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Twenty years ago, Kevin Brown made baseball history when he signed the sport’s first $100 million contract; technically, a seven-year, $105 million deal with the Los Angeles Dodgers.

Now? There have been 85 such deals, the most recent being Ronald Acuna’s eight-year, $100 million extension.

For a long time, Alex Rodriguez held the honor of baseball’s loftiest contract at $252 million, and then he one-upped himself with a $275 million deal. This offseason alone, there have been four contracts handed out in the vicinity of A-Rod’s extensions: Mike Trout (12 years, $430 million), Bryce Harper (13 years, $330 million), Manny Machado (10 years, $300 million), and Nolan Arenado (eight years, $260 million).

You can’t fully evaluate a contract until the end – but you can get a pretty good idea right away. Case in point: Albert Pujols’ 10-year, $240 deal with the Los Angeles Angels extends through the 2021 season, but if given a mulligan on said contract, you know the Angels would take it. Pujols is just a .260/.315/.453 hitter with the Angels, having hit 188 home runs in seven seasons, earning just a single All-Star selection, and posting only 13.2 WAR (per Baseball Reference) during that span. He still has three years remaining on his contract, but chronic foot issues and rapidly declining plate discipline have reduced him to being a liability both at the plate and in the field.

Paying $168 million thus far for just over 13 wins above replacement is not likely what the Angels had in mind. That comes out to an average of just 1.89 WAR per year and $12.73 million paid per single WAR.

But what about other notable contracts? How does Robinson Cano’s 10-year, $240 million contract compare to that of others? What about Jon Lester’s six-year, $155 million contract? Or $175 million over seven years for Felix Hernandez? I looked at every player’s WAR and compared it to his AAV (average annual value), but also looked at other factors – All-Star selections, Cy Young or MVP awards, and World Series rings. Leading a team to a single world championship doesn’t in fact make the contract in itself worth it, but it sure does help.

I also looked at the number of teams the player played for during his contract. If a player is shipped out after one year of his contract and suits up for four different teams (as was the case of Jose Reyes), that’s a clear indicator the contract was a mistake.

Of the 85 such nine-figure contracts, five don’t even begin until the 2020 season – Alex Bregman, Chris Sale, Paul Goldschmidt, Jose Altuve, and Xander Bogaerts. Another seven just started in ’19 – Trout, Harper, Machado, Arenado, Patrick Corbin, Jacob deGrom, and Acuna. I removed these 12 contracts from the rankings, meaning this is a ranking of the 73 qualifying contracts. For what it’s worth, it’s difficult to rank the contracts that just started in 2018, but that’s where the ranking is largely based on a one-year sample size and a projection going forward.

Additionally, I did not factor in inflation. A $100 million contract 10 years ago is worth more now, but it’s difficult to know how to compare them to one another. With that in mind, let’s start with a contract that may go down as the worst one ever signed by a professional athlete.

73. Chris Davis, Baltimore Orioles (2015-2021)

Contract: 7 years, $161 million

Years Played: 3

Total WAR: 0.5

WAR/Year: 0.17

Cost Per 1 WAR: $138 million

We’ve seen teams hand out big contracts to players before and realize early on that it’s a mistake, but what we’re witnessing from the Chris Davis deal takes it to historic proportions. Since signing his deal, he’s a .200 hitter with strikeouts in 36 percent of his plate appearances. He hit a meager .168 in 2017 and threatened to break the single-season record for lowest WAR ever by a position player. I’ve said I won’t even factor in what has happened this far in 2019, but it’s difficult to ignore the fact that his 0-fer streak extended past 50 at-bats, setting a new major league record for position players. At this point, it may make sense for the Orioles to simply pay Davis out the rest of his money and release him.

72. Ryan Howard, Philadelphia Phillies (2012-2016)

Contract: 5 years, $125 million

Years Played: 5

Total WAR: -4.5

WAR/Year: -0.90

Cost Per 1 WAR: -$27.78 million

It’s not Ryan Howard’s fault that the Phillies handed him a $125 million extension early in 2010, one that wasn’t scheduled to start for two more seasons. But after suffering a torn Achilles on the final at-bat of the 2011 NLDS, Howard was never again the same player. He batted just .226 over the ensuing five years, averaging just 19 home runs per season, leading the league in strikeouts once, and ranking dead-last among all position players in WAR (-4.5) over that span. Remarkably enough, teams just haven’t picked up on the fact that signing one-dimensional power hitters to large contracts can be disastrous; see Albert Pujols, Miguel Cabrera, and Prince Fielder.

71. Josh Hamilton, Los Angeles Angels of Anaheim (2013-2017)

Contract: 5 years, $125 Million

Years Played: 5

Total WAR: 3.2
WAR/Year: 0.64

Cost Per 1 WAR: $39.06 million

Despite going first overall in the 1999 MLB draft, winning a league MVP award, hitting four home runs in a game, and blasting a record-setting 28 home runs in the 2008 Home Run Derby, Josh Hamilton is probably best known for what could have been. His career was frequently derailed by an unfortunate alcohol and drug addiction as well as numerous injuries that eventually forced him into early retirement. After signing his five-year contract, Hamilton just .255 with 31 home runs in two years with the Angels, and then was subsequently traded back to Texas after word of his relapse emerged. Hamilton lasted one year in Texas before knee problems ended his playing days.

70. Mike Hampton, Colorado Rockies (2001-2008)

Contract: 8 years, $121 million

Years Played: 8

Total WAR: 2.9
WAR/Year: 0.36

Cost Per 1 WAR: $41.72 million

The Colorado Rockies were apparently giddy over Mike Hampton’s 22-4 record with the Houston Astros in 1999 and thus inked him an offseason later to what was then the largest contract ever handed out to a pitcher. Hampton was a disaster on the mound in two seasons in Coors Field, posting a 21-28 record to go with a 5.75 ERA (the highest among all qualifying starting pitchers over that span) before he was shipped off to Atlanta. Hampton is possibly the best-hitting pitcher our generation has ever seen, blasting 10 home runs in his two years with the Rockies, but you don’t hand out $121 million for a pitcher who can hit.

69. Homer Bailey, Cincinnati Reds (2014-2019)

Contract: 6 years, $100 million

Years Played: 5

Total WAR: -1.2
WAR/Year: -0.24

Cost Per 1 WAR: -$72.92 million

If a $100 million deal seemed a little steep for a pitcher who fashioned a 4.25 career ERA at the time of signing, Homer Bailey has proven that it was indeed a colossal mistake. In five years since, he’s 18-32 with a 5.27 ERA including back-to-back 6.00-plus ERA seasons that saw him shipped to Kansas City for the final year of his deal. To date, he’s one of only three players to have accumulated negative WAR during his $100 million contract.

68. Albert Pujols, Los Angeles Angels of Anaheim (2012-2021)

Contract: 10 years, $240 million

Years Played: 7

Total WAR: 13.2
WAR/Year: 1.89

Cost Per 1 WAR: $12.73 million

The red flags were there even before Albert Pujols signed his $240 million deal in free agency. After 11 Hall of Fame seasons and a pair of world championships in St. Louis, he was coming off career-lows in hits (173), RBIs (99), and walks (61), as well as worsts in every major slash line percentage. If signing a 32-year-old slugger with bad knees to a near-historic deal seemed like a questionable move at the time, it has aged even worse.

At this point, Pujols can’t move very well and he’s been rendered to that of a DH with declining bat speed and subpar plate discipline. Pujols was a .328/.420/.617 hitter in St. Louis; he’s a .260/.315/.452 hitter in LA with three seasons still to go at a total of $87 million. The Angels probably thought they’d at least see Pujols put up a serious challenge to Barry Bonds’ career home run record, but at 633 home runs entering 2019, he likely won’t even reach 700.

67. Barry Zito, San Francisco Giants (2007-2013)

Contract: 7 years, $126 million

Years Played: 7

Total WAR: 2.4
WAR/Year: 0.34

Cost Per 1 WAR: $52.50 million

A onetime Cy Young award winner in Oakland, Barry Zito’s track record of success and remarkable durability at least suggested he might come close to fulfilling a mammoth free agent contract in San Francisco. What actually happened was that he turned in five straight losing seasons and was then left off the Giants’ postseason roster in 2010 (they won the World Series without him). Zito at least rebounded to go 15-8 for the ’12 team, outdueling reigning league MVP Justin Verlander in his lone World Series start and helping the Giants win a world championship. You can argue how much of a factor Zito was on those ’10 and ’12 Giants teams, but still, two titles in a three-year span can never be taken away and keeps him from a bottom-five ranking.

66. Miguel Cabrera, Detroit Tigers (2016-2023)

Contract: 8 years, $248 million

Years Played: 3

Total WAR: 4.6
WAR/Year: 1.53

Cost Per 1 WAR: $20.22 million

The physical and statistical similarities between Albert Pujols and Miguel Cabrera were uncanny; you’d think maybe Detroit would have realized that handing out $248 million over eight years to Cabrera was a bit too much given his body type and defensive limitations. And credit to FanGraphs for calling this as an awful deal at the time of signing.

Cabrera will be 40 years old and earning $32 million when his contract finishes up; the problem is that he played in just a combined 168 games during his age-34 and age-35 seasons from 2017-2018. If his body is breaking down already, that’s not a good sign for the foreseeable future. Cabrera is at 465 home runs; if he can play a DH role and hit .290 with 25 home runs and push for 600 home runs by the time 2023 rolls around, the Tigers would probably take that at this point.

65. David Wright, New York Mets (2013-2020)

Contract: 8 years, $138 million

Years Played: 6

Total WAR: 9.1
WAR/Year: 1.52

Cost Per 1 WAR: 11.37 million

The Mets couldn’t possibly have known David Wright’s back would give out so early into his contract. He was an All-Star in 2013 and still a productive player in 2014, but then injuries limited him to just 77 total games over the next four years before he was forced to retire. He’s still being paid $15 million in 2019 and $12 million in 2020. When it’s all said and done, the Mets will have paid a grand total of $138 million for just 9.1 total WAR.

64. Matt Cain, San Francisco Giants (2012-2017)

Contract: 6 years, $127 million

Years Played: 6

Total WAR: 2.7
WAR/Year: 0.45

Cost Per 1 WAR: $47.04 million

In totality, the Matt Cain contract was a disaster, as he never came close to duplicating his first year after signing the deal (16-5, 2.79 ERA, 193 strikeouts). But like Barry Zito, he played a pivotal role in a World Series championship, tossing seven strong innings in his lone Fall Classic start to help the Giants win a title. Cain’s final five years included a 19-40 record to go with a 4.82 ERA and 1.381 WHIP, but it’s the strong campaign in the title year that keeps him from ranking lower on the list.

63. Carl Crawford, Boston Red Sox (2011-2017)

Contract: 7 years, $142 million

Years Played: 7

Total WAR: 3.7
WAR/Year: 0.53

Cost Per 1 WAR: $38.38 million

Carl Crawford was a near-.300 career hitter who led the league in triples four times and steals four times before signing with Boston, but the problem is when you’re a 30-year-old without power and you begin to lose your speed, you’re not going to be worth $20 million per year. Crawford didn’t even make it full his whole contract; in six disappointing seasons with Boston and then the Los Angeles Dodgers, he amassed a .271 career batting average, 32 home runs, and 71 steals and dealt with a slew of injuries that saw him miss over half of his team’s games. Los Angeles paid out $35 million to release him after 2016.

62. Prince Fielder, Detroit Tigers (2012-2020)

Contract: 9 years, $214 million

Years Played: 7

Total WAR: 6.8
WAR/Year: 0.97

Cost Per 1 WAR: $24.48 million

It’s an interesting move to give a 275-pound first baseman $214 million in guaranteed money over a nine-year span; in fact, at the time that Detroit signed Prince Fielder, it was the fourth-highest total contract handed out to a player in baseball history – and two of those belonged to Alex Rodriguez. Fielder started out well, averaging .295 with 28 home runs and 107 RBIs over his first two seasons, while even leading the Tigers to a World Series appearance. Then Detroit traded him to Texas for Ian Kinsler, but hit just .269 with 34 home runs over parts of the next three seasons before multiple neck surgeries forced him into early retirement. It’s not Fielder’s fault he got hurt, but still, it leaves a lot to be desired on his contract.

61. Vernon Wells, Toronto Blue Jays (2008-2014)

Contract: 7 years, $126 million

Years Played: 7

Total WAR: 6.6
WAR/Year: 0.94

Cost Per 1 WAR: $19.09 million

There have been worse contacts than Vernon Wells, but he turned in pretty subpar performances for a player making $18 million over seven years. He averaged 22 home runs and 2.3 WAR from 2008-2010, then spent two mediocre years with the Angels, and then a dreadful year with the Yankees. In addition to being just a .255/.302/.433 hitter during the length of his contract, Wells was also a vastly subpar defense in center and left field.

60. Ryan Zimmerman, Washington Nationals (2014-2019)

Contract: 6 years, $100 million

Years Played: 5

Total WAR: 3.9
WAR/Year: 0.78

Cost Per 1 WAR: $21.37 million

Even more so than Bryce Harper, Ryan Zimmerman has been the face of the Washington Nationals for 15 years now. He was the team’s first-ever draft pick (fourth overall in 2005) and he’s the franchise’s all-time leader in home runs (265), runs batted in (995), and WAR (38.0). The only problem is that his current six-year, $100 million contract… is kind of a disaster. Zimmerman’s body just hasn’t withstood the wear and tear of playing regularly; in five seasons so far, he’s only suited up for even 100 games twice, and he’s missed 38 percent of his team’s contests. His career contributions to the team have been impressive, but 3.9 total WAR through five years of a $100 million contract is underwhelming.

59. Yu Darvish, Chicago Cubs (2018-2023)

Contract: 6 years, $126 million

Years Played: 1

Total WAR: -0.1
WAR/Year: -0.1

Cost Per 1 WAR: -$210 million

We’re only one season into the Yu Darvish contract, which means he has ample time to turn things around. But if 2018 was a sign of what’s to come, Theo Epstein may have issued even a worse contract than the Jason Heyward one. Darvish made just eight starts last year, winning one game and posting a 4.95 ERA. While I said I wouldn’t factor the small sample size of 2019 into my ranking, it’s hard to ignore the fact that he issued 11 walks in his first two outings. There’s plenty of time for Darvish to turn this around, but he also hasn’t been an effective pitcher in two full calendar years. This is worth monitoring.

58. Jordan Zimmermann, Detroit Tigers (2016-2020)

Contract: 5 years, $110 million

Years Played: 5

Total WAR: 1.2
WAR/Year: 0.4

Cost Per 1 WAR: $55.00 million

After years of being an underrated piece of the Washington Nationals, Jordan Zimmermann inked a $22 million-a-year deal with Detroit – and has been near-replacement level, save for one glorious month to start his Tigers tenure. In his first five outings in Detroit back in 2016, Zimmermann allowed a grand total of two earned runs and earned AL Pitcher of the Month honors. Aside from that, he’s been replacement-level over three seasons. Zimmermann is 19-28 with a 5.68 ERA since those first five starts and he’s missed significant time to an assortment of injuries. Hopefully he turns it around over the next two seasons, but don’t count on it.

57. Jose Reyes, Miami Marlins (2012-2017)

Contract: 6 years, $106 million

Years Played: 6

Total WAR: 9.1
WAR/Year: 1.52

Cost Per 1 WAR: $11.65 million

As it currently stands, Jose Reyes is the only man ever to sign a $100 million deal in free agency and not make it to year two with that team; he’s also the only player ever to suit up for four different ballclubs during the duration of the contract. He actually fared well in Miami in 2012, batting .287 with 60 extra-base hits, 40 steals, and a 3.0 WAR but was traded to Toronto that offseason in a massive trade that involved 12 total players. Reyes’ remaining five years were characterized by nagging soft tissue injuries and an ugly domestic violence assault charge as he bounced from team to team. Fortunately, he barely cracked the $100 million threshold, so he doesn’t rank as low as others on the list.

56. Matt Kemp, Los Angeles Dodgers (2012-2019)

Contract: 8 years, $160 million

Years Played: 7

Total WAR: 5.0
WAR/Year: 0.71

Cost Per 1 WAR: $28.00 million

The biggest problem with Matt Kemp’s production during the life of his contract hasn’t been his offense. Sure, you’d like more than a .279/.328/.480 statline with 152 home runs in seven years thus far, but it’s the defensive metrics are alarming. Kemp’s -96 defensive runs saved since signing his contract rate him as the single-worst defender in baseball; this after he won a Gold Glove and nearly the league MVP award in 2011. He’s been porous enough that he hasn’t even cleared one WAR per year.

55. Alfonso Soriano, Chicago Cubs (2007-2014)

Contract: 8 years, $136 million

Years Played: 8

Total WAR: 8.9
WAR/Year: 1.11

Cost Per 1 WAR: $15.28 million

Alfonso Soriano picked the perfect time to have his best year; he parlayed the majors’ fourth 40 HR-40 SB season ever (41-46 in 2007) into an eight-year, $136 million contract with the Chicago Cubs. Soriano’s power numbers stayed up during his contract, as he averaged 26 home runs and 75 runs batted in for the duration, but his awful plate discipline (.313 on-base percentage and 121 strikeouts per year) limited his overall offensive value. To be fair, he at least made two All-Star teams during his contract, even if 8.9 WAR is a low total for what was at the time the fifth-largest contract ever signed.

54. Jacoby Ellsbury, New York Yankees (2014-2020)

Contract: 7 years, $153 million

Years Played: 7

Total WAR: 9.9
WAR/Year: 1.98

Cost Per 1 WAR: $11.04 million

Like Johnny Damon, Jacoby Ellsbury went from the Boston Red Sox to the enemy, signing a long-term deal to wear the evil pinstripes. The Yankees must have been thinking Ellsbury could duplicate his onetime 32-home run production when they signed him to a ridiculous contract that averaged $22 million per year over seven years. So far, Ellsbury has been a .264 hitter in the Bronx who averages 20 steals a season and plays solid defense in center field. That’s not bad but it’s not worth what he’s earning, especially since Ellsbury hasn’t even played since 2017 due to hip and foot injuries. If Ellsbury can’t return to the field, he’s going to plummet on this list.

53. Jason Heyward, Chicago Cubs (2016-2023)

Contract: 8 years, $184 million

Years Played: 3

Total WAR: 5.1
WAR/Year: 1.70

Cost Per 1 WAR: $13.53 million

Through three seasons, it’s looking as if the Cubs gave Jason Heyward a $23 million-per-year deal to be a Gold Glove right fielder and a replacement-level hitter (plus a dynamic motivational speaker). Heyward was atrocious in the 2016 postseason (5-for-48; a .104 batting average) before giving The Speech Heard ‘Round the World that may or may not have helped Chicago win its first World Series championship in 108 years. We’ll pretend that Heyward’s speech makes 2016 worth it, but aside from that, his play in the field gives claim to the argument that Major League Baseball should institute a designated fielder who never has to bat.

52. Eric Hosmer, San Diego Padres (2018-2025)

Contract: 8 years, $144 million

Years Played: 1

Total WAR: 1.4
WAR/Year: 1.40

Cost Per 1 WAR: $12.86 million

Eric Hosmer is the player version of the antithesis of the San Francisco Giants; while the Giants won the World Series in even years 2010, 2012, and 2014, Hosmer has been at his best in odd years 2013, 2015, and 2017. Fortunately for him, his free agency bid correlated with an odd year and thus a 318/.385/.498 line to go with 25 home runs, 94 RBIs, and a 4.1 WAR. Unfortunately for San Diego, they reaped the even year Hosmer in ’18, as he batted just .253 with 18 home runs and a 1.4 WAR. If Hosmer continues his every other year trend, he could be a semi-productive player, but still, it’s difficult to see this contract being worth it by 2025.

51. Ken Griffey, Jr., Cincinnati Reds (2000-2008)

Contract: 9 years, $116 million

Years Played: 9

Total WAR: 13.3
WAR/Year: 1.48

Cost Per 1 WAR: $8.72 million

For the entire 1990s, Ken Griffey, Jr. was THE face of the sport. He was everyone’s favorite player and had the sweetest swing this game has seen since… maybe ever. The mere fact that he was allowed to leave Seattle in the first place was hard to comprehend, and that the Mariners let Randy Johnson, Griffey, and Alex Rodriguez all leave in successive seasons – and then won a record-tying 116 games – defies all odds.

Griffey made three All-Star teams in Cincinnati and smacked over 200 home runs, but he never came close to being the player he was in Seattle. Nagging lower leg injuries constantly derailed his playing time, as he missed nearly one-third of available games over nine years. Griffey accumulated just 13.3 wins above replacement in his Reds tenure, and over half of that came in his first two years.

50. Evan Longoria, Tampa Bay Rays (2017-2022)

Contract: 6 years, $100 million

Years Played: 2

Total WAR: 5.4
WAR/Year: 2.70

Cost Per 1 WAR: $6.17 million

It may have seemed like a good idea in November 2012 for the Rays to lock up Evan Longoria for a six-year extension that went through 2022. That way you have the franchise’s all-time leader in WAR and home runs playing out the rest of his potential Hall of Fame career with the team. But decline started earlier than expected for Longoria, and the Rays shipped him to San Francisco just one year into the six-year extension. He’s still an above-average third baseman but it’s doubtful his production matches the $73 million he’s still owed through the 2022 campaign.

49. Carlos Lee, Houston Astros (2007-2012)

Contract: 6 years, $100 million

Years Played: 6

Total WAR: 8.4
WAR/Year: 1.40

Cost Per 1 WAR: $11.90 million

Carlos Lee provided solid offensive production during the first three years of his contract, maintaining a .305/.354/.524 slash line and averaging 29 home runs and 107 runs batted in per season. But he declined faster than expected, posting just 1.5 total WAR over the final three seasons. Lee never had good plate discipline but his subpar speed and poor defense even in left field didn’t help his overall value.

48. Jayson Werth, Washington Nationals (2011-2017)

Contract: 7 years, $126 million

Years Played: 7

Total WAR: 8.8
WAR/Year: 1.26

Cost Per 1 WAR: $14.32 million

During his peak with the Philadelphia Phillies, Jayson Werth was an underrated asset – a power-hitting right fielder with elite speed and the ability to extend at-bats regularly. The Phillies would have loved to have kept him, but even much-maligned GM Ruben Amaro, Jr. knew he couldn’t possibly commit $126 million to Jayson Werth. Werth wasn’t awful with the Nationals by any stretch; after all, they won the division four times with him after having won none before his arrival. Werth’s patience at the plate resulted in a .355 on-base percentage and adjusted OPS 13 percent better than league average. Injuries and poor defense kept his overall value down, and when you look at Werth’s overall contributions during the duration of the contract, it’s doubtful the Nationals would do it over again if given the choice.

47. Troy Tulowitzki, Colorado Rockies (2011-2010)

Contract: 10 years, $157 million

Years Played: 8

Total WAR: 23.8
WAR/Year: 2.98

Cost Per 1 WAR: $5.28 million

For the first half of his megadeal, Troy Tulowitzki was one of the game’s best shortstops, making four All-Star squads, batting .303, and averaging 20 home runs per season while playing strong defense. But then he was traded to Toronto and the Blue Jays eventually ate $38 million of Tulowitzki’s remaining contract to release him. He’s since latched on with the Yankees, but the fact that he will have provided very little value on the back end of this contract has to bring his ranking down.

46. Shin-Soo Choo, Texas Rangers (2014-2020)

Contract: 7 years, $130 million

Years Played: 5

Total WAR: 7.3
WAR/Year: 1.46

Cost Per 1 WAR: $12.72 million

Shin-Soo Choo’s best attribute is his on-base percentage; he’s just a .276 career hitter (.260 since signing his contract), but his propensity to draw a high number of walks keeps his on-base percentage and thus his adjusted OPS up. He has medium-range power and made his first All-Star team in 2018. His contract will never go down as a bust, but similarly to Jayson Werth, it’s questionable that his team felt he was worth as much as they paid him.

45. Alex Rodriguez, New York Yankees (2008-2017)

Contract: 10 years, $275 million

Years Played: 10

Total WAR: 23.3
WAR/Year: 2.33

When you think of all-time great players to don the Yankees pinstripes, you think of Babe Ruth. Lou Gehrig. Mickey Mantle. Derek Jeter. Joe DiMaggio. Reggie Jackson. You don’t think of Alex Rodriguez. While he actually spent more time with the Yankees than any other team, it’s fair to say he was never fully embraced by the fans or media there. Ownership thought highly enough of him to hand out a $275 million contract to a 32 ½ year-old player in 2007, and they had to be hoping they would have him in uniform when he eventually broke Barry Bonds’ career home run record. What actually happened was a decade mired with controversy over A-Rod’s alleged and then admitted steroid usage, resulting in a year-long suspension and a forever-tarnished image. A slew of hip/knee injuries also kept Rodriguez out of action for extended periods of time, leading the Yankees to eventually release him/force him into early retirement in August 2016. There will always be the 2009 World Series championship in which A-Rod finally got over his postseason struggles by batting .365 in 15 playoff games, but there wasn’t enough consistent star production to make the deal worth it, especially at that price range.

44. Yoenis Cespedes, New York Mets

Contract: 4 years, $110 million

Years Played: 2

Total WAR: 3.1
WAR/Year: 1.55

Cost Per 1 WAR: $17.74 million

It’s a wonder the Mets couldn’t get Yoenis Cespedes for cheaper than $27.5 million per season over four years. They had to be hoping for 30 home runs and 100 RBIs per year; instead, they’ve gotten a total of 26 home runs and 71 RBIs over two seasons, with Cespedes missing 205 of a possible 324 games due to injury. There’s still time for Cespedes to turn it around but he’s not trending the right way so far.

43. Johnny Cueto, San Francisco Giants (2016-2021)

Contract: 6 years, $130 million

Years Played: 3

Total WAR: 8.8
WAR/Year: 2.93

How Johnny Cueto rebounds from last year’s Tommy John surgery will impact his overall slot on these rankings. He turned in a strong first season, winning 18 games, starting for the National League in the All-Star Game, and leading the Giants to a playoff appearance. Since then, Cueto has struggled to stay on the mound, dealing with a forearm injury, an elbow sprain, and eventually Tommy John surgery. Cueto isn’t the first pitcher to go under the knife and there are reasons to believe he can return to form when he’s back at the end of 2019 or early in 2020.

42. CC Sabathia, New York Yankees (2012-2016)

Contract: 5 years, $122 million

Years Played: 5

Total WAR: 7.1
WAR/Year: 1.4

Cost Per 1 WAR: $17.18 million

CC Sabathia’s five-year, $122 million contract he signed before 2012 was technically a reworking of his initial seven-year, $161 million deal, but we’ll evaluate them separately as was the case for Alex Rodriguez, Justin Upton, and others who signed similar contracts before their initial deal ended. Sabathia was fairly durable during his five-year deal (save for 2014), but the problem was that he just wasn’t that effective. In 127 starts, Sabathia was 47-45 with a 4.25 ERA, one that placed him slightly below league-average standards by adjusted ERA (97). He made an All-Star team and led the league in strikeout-to-walk ratio once, but that’s not $25 million-per-year production.

41. Adrian Gonzalez, Boston Red Sox (2012-2018)

Contract: 7 years, $154 million

Years Played: 7

Total WAR: 15.7
WAR/Year: 2.24

Cost Per 1 WAR: $9.81 million

It’s curious that the Red Sox signed Adrian Gonzalez to a $154 million extension in April 2011, and then traded him away just 16 months later, not even one full year into the new contract. Boston paid Gonzalez to be a power hitter and RBI machine, and that’s exactly what he was. Gonzalez averaged 23 home runs and 101 runs batted in during his first five seasons before injuries ended his effectiveness as a player. His 2.24 WAR per year average puts him squarely in the middle of the pack in terms of production.

40. Ryan Braun, Milwaukee Brewers

Contract: 5 years, $105 million

Years Played: 3

Total WAR: 6.7
WAR/Year: 2.23

Cost Per 1 WAR: $9.40 million

If you thought Evan Longoria’s contract extension was premature, the Brewers actually once signed Ryan Braun to a five-year extension that wasn’t set to start for five more years. Braun won the MVP award the year they signed him and finished runner-up the following year, but by the time the start of his new extension rolled around, Braun had a nasty PED suspension on his resume. He’s been a solid player since inking the deal – hitting .279/.341/.502 with an average of 22 home runs and 69 RBIs per year – but it’s highly doubtful the Brewers would have signed him had they known of his upcoming steroid allegation.

39. Kevin Brown, Los Angeles Dodgers (1999-2005)

Contract: 7 years, $105 million

Years Played: 7

Total WAR: 22.8
WAR/Year: 3.26

Cost Per 1 WAR: $4.61 million

The infamous Kevin Brown contract has taken a lot of slack over the years, especially considering $105 million back in 1999 projects as much more money 20 years later. The fact that Brown’s contract included chartered plane flights isn’t factored in, and there’s no way to deny that the Dodgers paid a heck of a lot of money for a 34-year-old pitcher. But Brown’s contract wasn’t as bad as people pretend it was; he gave LA a handful of strong seasons, winning 58 games in all, capturing an ERA title, and making multiple All-Star teams. The Dodgers eventually traded him to the Yankees where Brown endured a nightmarish two years that included a broken hand from punching a wall, a horrific start in Game 7 of the 2004 ALCS, and inclusion in the infamous Mitchell Report.

38. Felix Hernandez, Seattle Mariners (2013-2019)

Contract: 7 years, $175 million

Years Played: 6

Total WAR: 17.0
WAR/Year: 2.83

Cost Per 1 WAR: $8.82 million

By starting his major league career at just age 19, King Felix already had over 1,600 innings under his belt when he signed his $175 million extension, then the largest deal ever handed out to a pitcher. The Mariners will be glad when the deal expires after this year, but in reality, it was a solid investment. Hernandez is 70-52 with a 3.53 ERA since signing his contract, earning three All-Star selections and winning a league ERA title. He’s been a liability the last few seasons, but he’s still produced 17.0 WAR during the duration of the deal.

37. Masahiro Tanaka, New York Yankees (2014-2020)

Contract: 7 years, $155 million

Years Played: 5

Total WAR: 15.6
WAR/Year: 3.12

Cost Per 1 WAR: $7.10 million

A $155 million contract is a lot of money to hand out to a pitcher who had never before pitched in the major leagues, but hey, it’s the Yankees. Tanaka has been a solid starter since inking his deal, winning between 12 and 14 games every year and posting a 3.59 ERA to go with a stellar 4.99 K:BB ratio. He probably hasn’t been as dominant as the team had hoped and he’s still never topped 200 innings in a single season; that being said, there’s a good chance he’s performed well enough to earn an extension from the Yankees after 2020.

36. Johan Santana, New York Mets (2008-2013)

Contract: 6 years, $137 million

Years Played: 6

Total WAR: 15.3
WAR/Year: 2.55

Cost Per 1 WAR: $8.95 million

For five seasons in Minnesota, Johan Santana was arguably the game’s most dominant pitcher, winning a pitching triple crown, two ERA titles, and three strikeout titles. Even after he was traded to the Mets, Santana turned in a trifecta of strong seasons. The problem is that his contract was for six years and at $23 million per year. From ’08-’10, Santana was good for a 40-25 record and a 2.85 ERA and then he added a no-hitter in 2012. If he had been able to stay healthy longer, there’s a good chance he would be in the Hall of Fame.

35. Charlie Blackmon, Colorado Rockies (2018-2023)

Contract: 6 years, $108 million

Years Played: 1

Total WAR: 0.8
WAR/Year: 0.8

Cost Per 1 WAR: $22.50 million

Charlie Blackmon is just one year into his six-year extension, but he batted .291 with 29 home runs, 12 stolen bases, and an NL-best 119 runs scored. That seems like terrific production but when you factor in Blackmon’s horrendous defense in center field (-28 defensive runs saved), Blackmon accounted for just 0.8 WAR. As long as he can provide consistently strong offensive production, the Rockies should be happy with Blackmon.

34. Mark Teixeira, New York Yankees (2009-2016)

Contract: 8 years, $180 million

Years Played: 8

Total WAR: 20.5
WAR/Year: 2.56

Cost Per 1 WAR: $8.78 million

There are only five players to have 1) finished a $100 million contract with the team that originally signed him 2) make multiple All-Star appearances and 3) lead the team to a World Series title. Mark Teixeira is one of them. His contract was a little long by the end, but still, he hit 206 home runs and drove in over 600 runs during an eight-year period. Teixeira won’t make the Hall of Fame, but still, this is a contract the Yankees would likely do again.

33. Joe Mauer, Minnesota Twins (2011-2018)

Contract: 8 years, $184 million

Years Played: 8

Total WAR: 21.9
WAR/Year: 2.74

Cost Per 1 WAR: $8.40 million

It’s fairly risky to sign a catcher to a $184 million contract, but the Twins did it and got fairly good results from Joe Mauer. He wasn’t the same player who won the 2009 AL MVP award and three batting titles, but still, for the duration of his contract, he was a .290/.372/.405 hitter who made two All-Star teams and played solid to above-average defense behind the plate. When you get close to three WAR per year from a backstopper, it’s pretty good production even if you’re paying quite a pretty penny for it.

32. David Price, Boston Red Sox (2016-2022)

Contract: 7 years, $217 million

Years Played: 3

Total WAR: 9.0
WAR/Year: 3.00

Cost Per 1 WAR: $10.33 million

At this point in time, no pitcher has ever received a larger contract than the $217 million Boston handed David Price. Price has leveled off a bit from the ace that won the 2012 American League Cy Young award, but he’s still 39-19 with a 3.74 ERA and a 9.0 K/9 rate since signing the deal. At $31 million per year, there isn’t much grace for Price to suffer any sort of injury or serious decline, but he’s also been fairly consistent over the last decade. The biggest reason Price’s contract has been worth it so far is that he delivered a World Series championship to Boston in 2018, finally getting over his past postseason struggles to win both World Series starts and post a 1.98 ERA in the process.

31. Justin Upton, Los Angeles Angels of Anaheim (2018-2022)

Contract: 5 years, $106 million

Years Played: 1

Total WAR: 3.8
WAR/Year: 3.80

Cost Per 1 WAR: $5.58 million

If it seems like five teams in his career is a lot for a perennial 30-home run guy to play for, that’s because it is. The Angels agreed to a five-year contract with Justin Upton, one that should keep him with the team through 2022, and he’s played well through one year. Upton hit 30 home runs and drove in 85 runs for the club in ’18, and that’s pretty much what they paid him to do.

30. Justin Upton, Detroit Tigers (2016-2021)

Contract: 6 years, $132.8 million

Years Played: 3

Total WAR: 11.4
WAR/Year: 3.80

Cost Per 1 WAR: $5.82 million

Upton is technically on the hook for two separate $100 million deals; the initial six-year, $132 million deal was re-written as a five-year, $106 million contract when he was traded to the Angels, but we’re going to grade the initial one as if it was a complete deal. When the Tigers traded Upton, they managed to do so without paying any dead money. What they got was 66 home runs and 196 RBIs in two years, and Upton put up similar production with LA in year three. That means he’s essentially been worth the money he’s been paid; it’s just unusual that Detroit decided to rid themselves of him so soon.

29. Elvis Andrus, Texas Rangers (2015-2022)

Contract: 8 years, $120 million

Years Played: 4

Total WAR: 12.0
WAR/Year: 3.00

Cost Per 1 WAR: $5.00 million

A $120 million deal may seem like too much to spend for a .276 career hitter with no power, but when you spread it over eight years, it’s a fine deal for Texas. Andrus is a top-10 shortstop who plays good defense and runs the bases well. As long as he stays on the field and can maintain a three WAR season, Texas will be happy with it.

28. Robinson Cano, Seattle Mariners (2014-2023)

Contract: 10 years, $240 million

Years Played: 5

Total WAR: 23.8
WAR/Year: 4.76

Cost Per 1 WAR: $5.04 million

It’s hard to believe a 31-year-old second baseman got $240 million in free agency, which at the time had only been topped in total value – at any position – by Alex Rodriguez (twice). Signing a future Hall of Famer like Robinson Cano and then getting an average of a .296/.353/.472 slash line plus 21 home runs and 4.8 WAR per year had to have been exactly what the Mariners’ organization was looking for. But you know what they weren’t looking for? An unfortunate PED suspension that hit Cano midway through 2018 and led to his being traded to the Mets with Seattle also paying $20 million in dead money. He’ll probably still finish his 10-year deal with at least 35 WAR and he’ll eventually get his 3,000^th hit, but this isn’t the way Seattle drew it up.

27. Zack Greinke, Arizona Diamondbacks (2016-2021)

Contract: 6 years, $206 million

Years Played: 3

Total WAR: 12.2
WAR/Year: 4.07

Cost Per 1 WAR: $8.44 million

Zack Greinke’s $34.33 million average annual salary is the highest ever handed out to a pitcher, and it’s almost impossible to fulfill those standards. Since signing his extension, Greinke is eighth in the major leagues in innings pitched (568.2), ninth in wins (45), and 13^th in strikeouts (548). He’s durable, consistent, and a great fielder (three Gold Gloves). And he’s giving the Diamondbacks consistently strong production. It’s just not reasonably worth over one million dollars per start.

26. Cliff Lee, Philadelphia Phillies (2011-2015)

Contract: 5 years, $120 million

Years Played: 5

Total WAR: 20.5
WAR/Year: 4.10

Cost Per 1 WAR: $5.85 million

During the first three years of his contract, Cliff Lee was second to only Clayton Kershaw among National League pitchers in innings pitched (666.1), strikeouts (667), and ERA (2.80), and no pitcher threw more shutouts (7) or posted a better K:BB ratio (6.54). Eventually, elbow issues caused him to miss half of the 2014 season and all of 2015, meaning he missed nearly 30 percent of his starts. Still, his greatness when he did pitch still puts him in the upper half of $100 million contracts signed.

25. Kyle Seager, Seattle Mariners (2015-2021)

Contract: 7 years, $100 million

Years Played: 4

Total WAR: 14.7
WAR/Year: 3.68

Cost Per 1 WAR: $3.89 million

A $100 million deal is steep for a career .258 hitter with no speed, but the average annual value of Kyle Seager’s contract ($14.29 million) ranks as the third-lowest, and makes his production so far worth it. Since signing his extension, Seager has played four seasons and accumulated 14.7 WAR while averaging 26 home runs and 85 RBIs per year. He’s an average defender at the hot corner and never gets injured; that makes his performances worth the money.

24. Stephen Strasburg, Washington Nationals (2017-2023)

Contract: 7 years, $175 million

Years Played: 2

Total WAR: 9.0
WAR/Year: 3.00

Cost Per 1 WAR: $5.56 million

There are still a lot of things that could go wrong with nearly $200 million committed to a pitcher who has already had Tommy John surgery and has cleared 185 innings in a year just once. Durability will likely always be the biggest concern with Strasburg, as he’s averaged just 153 innings in two seasons since signing his extension. When he does pitch, however, Strasburg is a top-10 pitcher; he’s 25-11 with a 3.04 ERA and terrific 10.6 K/9 rate.

23. Dustin Pedroia, Boston Red Sox (2014-2021)

Contract: 8 years, $110 million

Years Played: 5

Total WAR: 13.9
WAR/Year: 2.78

Cost Per 1 WAR: $4.95 million

An eight-year deal for a 30-year-old second baseman is a hefty price to pay, but $110 million makes for a pretty light per-year investment. Pedroia missed nearly all of 2018 due to injuries, but he was a .296 hitter and Gold Glove defender for the first half of the contract. If he can rebound to be a viable contributor for the final three years of his deal, he will move up this list.

22. Jon Lester, Chicago Cubs (2015-2020)

Contract: 6 years, $155 million

Years Played: 4

Total WAR: 12.4
WAR/Year: 3.10

Cost Per 1 WAR: $8.33 million

Jon Lester has been exactly as advertised during his six-year extension. He’s not an elite pitcher but he’s a workhorse and a guy you want on your side in big games. Lester has been 61-31 with a 3.33 ERA since signing the contract, making every start, leading the league in wins once, and finishing runner-up in the 2016 Cy Young award voting. And he’s been money in the postseason, posting a 2.42 ERA in 10 starts in the playoffs, and leading the Cubs to a World Series championship. The only thing keeping Lester from ranking higher is an AAV of nearly $26 million per year.

21. J.D. Martinez, Boston Red Sox (2018-2022)

Contract: 5 years, $110 million

Years Played: 1

Total WAR: 6.4
WAR/Year: 6.40

Cost Per 1 WAR: $3.44 million

The Red Sox paid J.D. Martinez to flat out hit the cover off the ball, and that’s exactly what he did in 2018. He batted .330/.402/.629 with 43 home runs, a league-leading 130 RBIs, and a fourth place finish in the AL MVP voting. And then he batted .300 in the postseason and helped deliver a World Series title back to Boston. That’s David Ortiz-like production. Martinez doesn’t play the field, but the Red Sox know that, and they’re paying him to do exactly what he did this past year.

20. Jason Giambi, New York Yankees (2002-2008)

Contract: 7 years, $120 million

Years Played: 7

Total WAR: 22.1
WAR/Year: 3.16

Cost Per 1 WAR: $5.43 million

$100 million contracts were still fairly new when Jason Giambi signed his in 2002, and he provided the Yankees with pretty solid value over seven years. He hit 40 home runs twice, topped 30 five times, and reached base at a spectacular .404 clip during the life of the contract. Even when his batting average dipped substantially, Giambi’s penchant for drawing walks and hitting home runs at a high rate kept him a viable slugger.

19. Cole Hamels, Philadelphia Phillies (2013-2018)

Contract: 6 years, $144 million

Years Played: 6

Total WAR: 26.7
WAR/Year: 4.45

Cost Per 1 WAR: $5.39 million

While he ended up pitching for three different teams during his six-year contract, Cole Hamels produced exactly as would have been expected given his career to date. He averaged nearly 200 innings per year, posting a 65-54 record to go with a 3.47 ERA and a 3.03 strikeout-to-walk ratio. He threw a no-hitter for the Phillies in his final start before they traded him in a rebuilding move, and then he made an All-Star team in notorious hitters’ park Texas. To date, no starting pitcher has ever completed a $100-plus million deal and averaged more WAR per year (4.45) than Hamels.

18. Matt Holliday, St. Louis Cardinals (2010-2016)

Contract: 7 years, $120 million

Years Played: 7

Total WAR: 20.9
WAR/Year: 2.99

Cost Per 1 WAR: $5.74 million

Five years into his seven-year deal, Matt Holliday was a .295 hitter who averaged 24 homers and 93 runs batted in per season. The contract dragged on by the end, but still, Holliday was a pleasant signing for St. Louis. Holliday is one of only three players in history to sign and complete a $100 million deal with the same team, earn at least four All-Star appearances, and lead that team to a title.

17. Zack Greinke, Los Angeles Dodgers (2013-2018)

Contract: 6 years, $147 million

Years Played: 6

Total WAR: 29.9
WAR/Year: 4.98

Cost Per 1 WAR: $4.92 million

Zack Greinke technically opted out of the last three years of his initial six-year contract, which is one of those advantages to a player – if he’s doing well enough to command more in free agency than he would have gotten over the remainder of his deal, he can always opt out. However, if Greinke had been a bust during his initial deal, he would have declined his opt-out, so in this sense, we’ll grade the six-year deal as if he carried it out. That means Greinke gets credit for the 96 wins and 2.90 ERA he posted during the life of the contract, as well as four All-Star appearances, five Gold Gloves, a Silver Slugger, and the lowest single-season ERA by a pitcher with over 200 innings pitched (1.66 in 2015) since Greg Maddux in 1995.

16. Joey Votto, Cincinnati Reds (2014-2023)

Contract: 10 years, $225 million

Years Played: 5

Total WAR: 24.4
WAR/Year: 4.88

Cost Per 1 WAR: $4.61 million

The Reds gave Joey Votto a mammoth decade-long deal because of his unbelievable ability to draw walks, and so far, that’s exactly what he’s done. Since 2014, Votto ranks first among all qualifying hitters in walks (540) and on-base percentage (.437). He’s fifth in batting average (.306) and he’s one of only five players with at least 100 home runs and a .300 batting average since ’14. It’s likely Votto’s deal will extend too long – he’s set to earn $25 million in 2023 when he’s 40 years old – but so far, Votto has proven to be on a Hall of Fame path.

15. CC Sabathia, New York Yankees (2009-2015)

Contract: 7 years, $161 million

Years Played: 7

Total WAR: 21.3
WAR/Year: 3.04

Cost Per 1 WAR: $7.56 million

CC Sabathia gave the Yankees four dynamic years after signing what was then the largest pitching contract ever, and that, plus the fact that he delivered the team to the 2009 World Series title, makes the deal well worth it. From 2009-’12, Sabathia averaged 18 wins, a 3.22 ERA, and 205 strikeouts per season, three times finishing in the top four in AL Cy Young award voting, and leading the league in wins twice. It was his performance down the stretch in 2009 that was especially memorable; Sabathia was 5-1 with a 2.39 ERA in September, then going 3-1 with a 1.98 ERA in the playoffs, including the ALCS MVP award.

14. Carlos Beltran, New York Mets (2005-2011)

Contract: 7 years, $119 million

Years Played: 7

Total WAR: 32.3
WAR/Year: 4.61

Cost Per 1 WAR: $3.68 million

This was just a solid all-around good deal for both player and team. While with the Mets, Carlos Beltran batted .282/.369/.503 with 156 home runs and 101 steals, earning five All-Star selections. He was a multi-time Gold Glover in the field, a top power/speed guy, and gave the Mets a strong performance with three home runs in seven games in the 2006 National League Championship Series. Only three other players have ever signed a seven-year, $100 million-plus deal and matched Beltran’s average WAR per year (4.61), and they’re all HOF-level players – Albert Pujols, Alex Rodriguez, and Miguel Cabrera.

13. Giancarlo Stanton, Miami Marlins (2015-2027)

Contract: 13 years, $325 million

Years Played: 4

Total WAR: 18.2
WAR/Year: 4.55

Cost Per 1 WAR: $5.49 million

Question for the Miami Marlins. When they signed Giancarlo Stanton to a 13-year deal worth over $300 million, did they anticipate trading him away within three years? Stanton struggled with injuries early on, but he led the major leagues with an astounding 59 home runs in 2017 – the highest single-season total we’ve seen since Barry Bonds (and Sammy Sosa) in ’01 – while winning the National League MVP award. There’s not much more a player can do to provide value to his team, and when you consider that the organization also traded away Christian Yelich and Marcell Ozuna, it’s apparent that Derek Jeter had his head set on ridding every asset the team had. From a production standpoint, Stanton has averaged 38 home runs and 93 RBIs since signing the deal, and that’s what you have to hope for from a player with his power.

12. Todd Helton, Colorado Rockies (2003-2011)

Contract: 9 years, $141 million

Years Played: 9

Total WAR: 32.7
WAR/Year: 3.63

Cost Per 1 WAR: $4.31 million

Even with the inevitable Coors Field boost, Todd Helton could flat out hit a baseball. He hit .320 five times during the length of his contract, posting a .316/.423/.508 statline in all with 161 home runs and and 685 runs batted in. Sure, his home/road splits were evident of how much he benefited from Colorado, but that’s a case for the Hall of Fame voters. From a contractual standpoint, his production was worth what the Rockies paid him.

11. Clayton Kershaw, Los Angeles Dodgers (2014-2020)

Contract: 7 years, $215 million

Years Played: 5

Total WAR: 29.0
WAR/Year: 5.80

Cost Per 1 WAR: $5.30 million

It’s truly difficult to be a bargain when you’ve signed a $30 million per year deal, especially one that goes for a total of over $200 million. And the inevitable injury-riddled decline of Clayton Kershaw may have already started, as he hasn’t topped 175 innings pitched since 2015 and has yet to pitch in ’19. Still, when he actually does pitch, he’s easily the game’s best pitcher. Kershaw is 76-23 with a 2.12 ERA over the last five years with a 7.48 K:BB ratio. Those are Sandy Koufax-esque numbers. Kershaw even won the 2014 National League MVP award for good measure. All he’s doing at this point is making a case to be considered a top-10 pitcher who ever lived.

10. Freddie Freeman, Atlanta Braves (2014-2021)

Contract: 8 years, $135 million

Years Played: 5

Total WAR: 23.5
WAR/Year: 4.70

Cost Per 1 WAR: $3.59 million

When you sign a player to a pre-free agency deal like the Braves did with Freddie Freeman, you can get him for substantially below market value. So far through five seasons of his contract, Freeman is a .297/.390/.517 hitter who averages 24 home runs and 81 RBIs per year and plays good defense. Only three other qualifying National League hitters have a higher league and park-adjusted OPS than Freeman (145). The way he’s been hitting the ball as of late, there’s likely an MVP award in Freeman’s near future.

9. Justin Verlander, Detroit Tigers (2013-2019)

Contract: 7 years, $180 million

Years Played: 6

Total WAR: 27.2
WAR/Year: 4.53

Cost Per 1 WAR: $5.67 million

When the Tigers signed Justin Verlander to what was at the time the largest contract ever handed out to a pitcher, it was a risky move. He was already 30 years old with over 1,500 innings on his right arm; three times he had led the AL in innings pitched. Impressively enough, Verlander has proven to be worth every penny of the lucrative deal he signed.

He’s 80-58 with a 3.38 ERA since signing the deal, twice finishing runner-up in the AL Cy Young award voting, and he’s proven his value to two teams. In fact he’ll go down as one of the greatest midseason trade acquisitions of all-time, going 5-0 with a 1.04 ERA in the regular season for the 2017 Houston Astros, winning ALCS MVP, and eventually leading them to their first-ever World Series championship. Verlander was even better for the ’18 Astros, striking out a career-high 290 batters, and playing well enough to earn a two-year, $66 million extension that will keep him in Houston through 2021.

8. Buster Posey, San Francisco Giants (2013-2021)

Contract: 9 years, $167 million

Years Played: 6

Total WAR: 28.5
WAR/Year: 4.75

Cost Per 1 WAR: $4 million

Not only are Buster Posey and Joe Mauer the only catchers in history to earn $150 million contracts, they’re actually the only catchers ever to even clear the $85 million barrier, meaning they’ve essentially doubled the next highest-paid catcher ever. Posey inked his contract fresh off a National League MVP award and World Series championship with the Giants, and he’s proven his value thus far in six years of the contract. Posey has batted .303 since signing his deal while playing strong defense behind the plate and leading the Giants to another World Series title; it’s that combination of skills that will one day put Posey in the Hall of Fame.

7. Max Scherzer, Washington Nationals (2015-2021)

Contract: 7 years, $210 million

Years Played: 4

Total WAR: 29.1
WAR/Year: 7.28

Cost Per 1 WAR: $4.12 million

When they signed him to a $210 million contract, there’s no way the Nationals could have imagined Max Scherzer would be this good. In four seasons, his average production has been 17-8 with a 2.71 ERA, 282 strikeouts, and a ridiculous 0.926 WHIP. He’s won multiple Cy Youngs, finished second another time, led the league in strikeouts and WHIP three times and wins twice, and he’s thrown a pair of no-hitters. It’s a performance that will land Scherzer in Cooperstown on the first ballot, and he’s shown absolutely no signs of slowing down.

6. Manny Ramirez, Boston Red Sox (2001-2008)

Contract: 8 years, $160 million

Years Played: 8

Total WAR: 36.7
WAR/Year: 4.59

Cost Per 1 WAR: $4.36 million

Manny Ramirez is one of those special human beings who was put on this earth to hit a baseball. It’s a wonder Cleveland let him leave in free agency, but Boston swooped in and signed him to a historic $160 million contract and got everything they could have wanted. In eight years, Manny Being Manny hit a ridiculous .315/.415/.595 with 291 home runs and 921 runs batted in, drawing enough walks to lead the league in on-base percentage three separate times. He got the Red Sox over the playoff hump in 2004, winning World Series MVP as the team captured its first title in 86 years, and then he put up another strong performance in ’07 as the Sox won their second championship in four seasons. When Ramirez was traded to the Dodgers midway through the ’08 campaign, he turned in one of the more absurd two-month stretches you’ll ever find, batting .396 in the regular season and then .520 in the postseason.

5. Derek Jeter, New York Yankees (2001-2010)

Contract: 10 years, $189 million

Years Played: 10

Total WAR: 41.3
WAR/Year: 4.13

Cost Per 1 WAR: $4.58 million

There are a lot of things that can go wrong with a 10-year contract, but this is Derek Jeter we’re talking about. Jeter batted .310 over the duration of his deal, hitting 156 home runs and stealing 215 bases. He was an All-Star nearly every year (eight in all), won multiple Gold Gloves, and led the Yankees to the playoffs every year but one. Oh, and he was the face of baseball who batted .407 in the 2009 World Series championship for the Yankees.

4. Miguel Cabrera, Detroit Tigers (2008-2015)

Contract: 8 years, $152 million

Years Played: 8

Total WAR: 46.6
WAR/Year: 5.83

Cost Per 1 WAR: $3.26 million

Before the Tigers gave Miguel Cabrera a $248 million extension that could get really ugly, there was his initial eight-year deal he signed soon after the then-Florida Marlins traded him to Detroit. Cabrera earned MVP votes in all eight seasons with the Tigers, finished in the top five on five occasions, won consecutive awards from 2012-2013, and even earned the game’s first Triple Crown award in nearly 50 seasons. The production he put up during that span (162 adjusted OPS) compares very favorably to the careers of Jimmie Foxx and Stan Musial.

3. Mike Trout, Los Angeles Angels of Anaheim (2015-2020)

Contract: 6 years, $144 million

Years Played: 4

Total WAR: 36.6
WAR/Year: 9.15

Cost Per 1 WAR: $2.62 million

You can’t really put a price on all-time greatness. The Angels tried to recently, overwriting the remaining two years of Mike Trout’s initial six-year contract with a record-breaking $430 million deal. The initial proportions of Trout’s $144 million contract are still in effect, and he’s absolutely blowing the value out of the water. In just four seasons so far, Trout has averaged over nine WAR per year, which means he’s been a viable MVP performer every year. If being the best hitter isn’t enough (league-leading totals in adjusted OPS every year), Trout is also a perennial 30-homer and 20-steal guy who shows remarkable control of the strike zone and robs home runs in center field.

2. Alex Rodriguez, Texas Rangers (2001-2010)

Contract: 10 years, $252 million

Years Played: 10

Total WAR: 71.4
WAR/Year: 7.14

Cost Per 1 WAR: $3.53 million

For close to 15 seasons, Alex Rodriguez’s contract was the precedent for all free agent players. It’s not often a 26-year-old shortstop with his abilities hits the open market, and it’s even more uncommon for that player to then blow the parameters of the deal out of the water in terms of production. In a recent article, FanGraphs suggested A-Rod’s then-$252 million contract would be worth nearly $600 million today; even so, that would represent a bargain for the performances he turned in – averaging over seven WAR per year.

In 10 years, A-Rod won three league MVP awards, led the AL in home runs five times, and averaged 42 homers and 124 RBIs per year. It’s not his fault that Texas couldn’t stomach the initial contract; after all, they traded A-Rod the offseason after he won the AL MVP award and led the major leagues in home runs. In New York, Rodriguez was every bit as valuable, even putting forth his best offensive output (2007) and then leading the team to a World Series title (2009) with a postseason performance that included a .365 batting average.

1. Albert Pujols, St. Louis Cardinals (2004-2010)

Contract: 7 years, $100 million

Years Played: 7

Total WAR: 60.6
WAR/Year: 8.66

Cost Per 1 WAR: $1.65 million

In terms of production compared to dollars paid, Albert Pujols’ contract remains the single greatest nine-figure deal ever signed. For a mere $100 million, he produced a seven-year stretch that on its own would put him in the Hall of Fame on the first ballot. Pujols’ 60.6 WAR gives him 8.66 WAR per year, the highest-ever total for a completed $100 million contract, and he checks in at just a mere $1.65 million per WAR.

From a non-sabermetric standpoint, Pujols batted .330/.432/.630 with 294 home runs, 849 RBIs, and an absurd 610 walks to just 367 strikeouts. Three times he was named NL MVP and on two other occasions, he was named runner-up. He was a terrific fielder who won multiple Gold Gloves and deserved a whole lot more. Pujols also delivered one of the most famous home runs in postseason history, derailing Brad Lidge’s career for two years, and then helped deliver a World Series championship to the 2006 Cardinals.

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