Every $25+ Million Contract

• SS Jay Bell, $34 million, 1998-2002
• LHP Randy Johnson, $52.4 million, 1999-2002
• RHP Todd Stottlemyre, $32 million, 1999-2002
• 3B Troy Glaus, $45 million, 2005-08
• RHP Russ Ortiz, $33 million, 2005-08
• OF Cody Ross, $26 million, 2013-15
• RHP Zack Greinke, $206.5 million, 2016-21
• LHP Madison Bumgarner, $85 million, 2020-24

Best: Randy Johnson

This may have been the greatest free-agent acquisition in MLB history. The Diamondbacks signed Johnson to a four-year deal, and he won the NL Cy Young in all four of those seasons, including a triple crown in 2002 with 24 wins, 334 strikeouts and a 2.32 ERA. And during Arizona’s World Series run in 2001, the “Big Unit” tossed 41.1 innings with a 1.52 ERA.

Worst: Madison Bumgarner

For a while, it was the Russ Ortiz contract. The Snakes cut him 1.5 years into that four-year deal with a hideous 7.00 ERA. Brutal production from a guy who was signed for a little over 10 percent of their annual payroll at the time. But Bumgarner wasn’t much better (5.23 ERA), and his $23 million salary in 2022 accounted for more than 25 percent of their Opening Day payroll. That’s much worse. They still have to pay him deferred money through 2027, too.

Every $25+ Million Contract

• RHP Greg Maddux, $28 million, 1993-97
• RHP John Smoltz, $31 million, 1997-2000
• OF Brian Jordan, $40 million, 1999-2003
• RHP John Smoltz, $30 million, 2002-04
• RHP Derek Lowe, $60 million, 2009-12
• OF B.J. Upton, $75.25 million, 2013-17
• OF Nick Markakis, $44 million, 2015-18
• LHP Will Smith, $40 million, 2020-22
• OF/DH Marcell Ozuna, $65 million, 2021-24

Best: Greg Maddux

If Randy Johnson wasn’t the greatest free-agent signing in MLB history, it’s probably Maddux signing with Atlanta, yeah? He won the NL Cy Young and led the majors in ERA in each of the first three years of this deal, and had overall marks of 2.13 ERA and 0.96 WHIP over the duration of that half-decade. He also made 15 postseason starts from 1993 to ’97 with a 2.38 ERA.

Worst: B.J. Upton

Atlanta has only once spent more than $65 million on a free agent, and it sure did regret that decision. In Upton’s two years with the Braves before they traded him and Craig Kimbrel to the Padres, he hit .198 and was worth negative-1.8 bWAR. He wasn’t even a starter anymore by the end of his first season and went 0-for-3 with three strikeouts as a pinch hitter/runner in the postseason.

Every $25+ Million Contract

• 1B Rafael Palmeiro, $30.35 million, 1994-98
• OF Brady Anderson, $31 million, 1998-2002
• OF Albert Belle, $65 million, 1999-2003
• SS Miguel Tejada, $72 million, 2004-09
• C Ramón Hernández, $27.5 million, 2006-09
• RHP Ubaldo Jiménez, $50 million, 2014-17
• RHP Darren O’Day, $31 million, 2016-19
• 1B Chris Davis, $161 million, 2016-22
• OF Mark Trumbo, $37.5 million, 2017-19
• RHP Alex Cobb, $57 million, 2018-21

Best: Rafael Palmeiro

Was he on PEDs at the time? We’ll never know. But Palmeiro sure was productive for the Orioles, batting .292 and mashing 182 home runs for five seasons in the mid-90s—two of which were truncated by the player’s strike, which probably kept him from averaging 40 dingers per year. While he didn’t finish top five in any of the votes, “Raffy” received MVP votes in each of those five years.

Worst: Chris Davis

The Ubaldo Jiménez signing certainly wasn’t great, amounting to 0.1 bWAR over the course of those four seasons. Making Albert Belle the highest-paid player in the game in 1999 didn’t go particularly well for Baltimore, either. But re-signing Davis to that megadeal legitimately broke this franchise for more than half a decade. “Crush” was solid for the first season of that monster contract, but he was worth negative-5.8 bWAR over his final four seasons before retiring with two years left on his deal.

Every $25+ Million Contract

• OF Manny Ramírez, $160 million, 2001-08
• OF J.D. Drew, $70 million, 2007-11
• RHP John Lackey, $82.5 million, 2010-14
• OF Carl Crawford, $142 million, 2011-17
• SS/OF Hanley Ramirez, $88 million, 2015-18
• 3B Pablo Sandoval, $95 million, 2015-19
• LHP David Price, $217 million, 2016-22
• OF/DH J.D. Martinez, $110 million, 2018-22
• RHP Nathan Eovaldi, $68 million, 2019-22
• SS Trevor Story, $140 million, 2022-27
• Guys who signed contracts with Boston worth $25-$50 million: Jason Varitek ($40M), Edgar Renteria ($40M), Shane Victorino ($39M), Mike Lowell ($37.5M), Julio Lugo ($36M), Mike Napoli ($32M), Kenley Jansen ($32M), Johnny Damon ($31M), Ryan Dempster ($26.5M), Jose Offerman ($26M), David Ortiz* ($26M), Keith Foulke ($25.5M), Matt Clement ($25M)

Best: Manny Ramírez

With honorable mentions to both J.D. Martinez and Johnny Damon, it’s hard to argue with the ROI Boston got from its eight-year deal with Ramírez. He was an All-Star in all eight seasons, hitting .312/.411/.588 with 274 home runs and a bunch of top-10 finishes for AL MVP. In 43 career postseason games with Boston, he had a .980 OPS with 11 home runs and two World Series titles. And even when the Red Sox traded him away with two months left on his deal, they replaced Ramírez with another MVP candidate, getting a fantastic year out of Jason Bay in 2009.

Worst: A tie between Pablo Sandoval and Carl Crawford

Though Crawford’s contract was for $47 million more than Sandoval’s, at least the Red Sox were able to con the Dodgers into taking the bulk of the outfielder’s deal after he appeared in just 161 games over his first two seasons with Boston. “Panda” also played in just 161 games for the Red Sox, and they got stuck paying that entire contract when they cut him in the third year of that deal. Forced to choose between the two, I’d have to go with Sandoval. But they were both horrific.

*Ortiz signed several extensions and short-term contracts with Boston, but the only $25+ million deal he signed as a free agent was a two-year contract before the 2013 season.

Every $25+ Million Contract

• 3B Aramis Ramirez, $75 million, 2007-11
• OF Alfonso Soriano, $136 million, 2007-14
• LHP Jon Lester, $155 million, 2015-20
• OF Jason Heyward, $184 million, 2016-23
• RHP Yu Darvish, $126 million, 2018-23
• RHP Marcus Stroman, $71 million, 2022-24
• RHP Jameson Taillon, $68 million, 2023-26
• SS Dansby Swanson, $177 million, 2023-29
• Guys who signed contracts with Chicago worth $25-$60 million: Ben Zobrist ($56M), Ryan Dempster ($52M), Edwin Jackson ($52M), Craig Kimbrel ($43M), Ted Lilly ($40M), Tyler Chatwood ($38M), John Lackey ($32M), Milton Bradley ($30M), Moises Alou ($27M)

Best: Jon Lester

Shouts to Moises Alou for giving Chicago three good seasons in his late 30s, and to Ben Zobrist, who was rock solid in his first year with the Cubs, culminating in a World Series MVP. But Lester played a much bigger role than Zobrist throughout that 2016 campaign and was also sensational in 2018. The last two years of his contract were a bit rough, and his career-long inability to pick off a baserunner became a comical punch line. Still, he was the ace of that championship team, which was worth every penny of his nine-figure deal.

Worst: Jason Heyward

In the first year of this albatross of a contract, the Cubs did finally win a World Series. But Heyward hit .104 with one RBI during the 2016 postseason, as they won that title in spite of him, not because of him. And it only got worse from there, as Heyward went from replacement level to unplayable to getting released with a year left on his deal. He was at least worth 9.0 bWAR for the Cubs, though. That probably keeps him from the No. 1 spot in a list of the worst contracts in MLB history.

Every $25+ Million Contract

• OF Albert Belle, $55 million, 1997-2001
• 1B Paul Konerko, $60 million, 2006-10
• 1B/DH Adam Dunn, $56 million, 2011-14
• LHP Dallas Keuchel, $55.5 million, 2020-22
• C Yasmani Grandal, $73 million, 2020-23
• RHP Liam Hendriks, $54 million, 2021-23
• OF Andrew Benintendi, $75 million, 2023-27
• Guys who signed contracts with Chicago worth $25-$50 million: José Abreu ($50M), David Robertson ($46M), Melky Cabrera ($42M), Paul Konerko ($37.5M), Adam LaRoche ($25M)

Best: José Abreu

Konerko’s five-year run from 2006 to ’10 was impressive, but he didn’t win an MVP like Abreu did in 2020. Abreu also received MVP votes in both 2021 and 2022, hitting .289 with a 10.1 bWAR in his last three seasons before relocating to Houston. While the team collapsed around him in 2022, he just kept hitting at a high level.

Worst: Yasmani Grandal

Grandal did at least play quite well in 2021 with a career-best OPS of .939. However, he only played in 93 games because of a leg injury and then was dreadful in both 2022 and 2023, ending his four-year run in Chicago with just a .718 OPS. His average fWAR for the five seasons before signing with the White Sox was 5.0. His total fWAR for those four years in Chicago was 4.7.

Every $25+ Million Contract

• LHP Eric Milton, $25.5 million, 2005-07
• RHP Francisco Cordero, $46 million, 2008-11
• 3B Nick Castellanos, $64 million, 2020-23
• 3B Mike Moustakas, $64 million, 2020-23

Best: Francisco Cordero

If the Reds had actually been able to keep Castellanos for all four years, he probably lands here with room to spare. Instead, he was able to opt out and sign a bigger contract with Philadelphia after his excellent 2021 campaign. So, give us Cordero, who saved 150 games with a sub-3.00 ERA in his four years with the Reds. It’s absurd that they made a closer their highest-paid player in both 2009 and 2011, but at least he was solid.

Worst: Mike Moustakas

Only four options for Cincinnati, but this might be a top 25 all-time awful MLB contract. In the three years before signing with Cincinnati, Moustakas hit a combined 101 home runs for the Royals and Brewers. But he turned 31 and just imploded. In three years with the Reds, he hit a grand total of 21 home runs and was released prior to the final season of his contract. He was worth negative-1.7 bWAR to the Reds.

Every $25+ Million Contract

• 2B Roberto Alomar, $32 million, 1999-2002
• LHP Chuck Finley, $27 million, 2000-02
• OF Nick Swisher, $56 million, 2013-16
• OF Michael Bourn, $48 million, 2013-16
• 1B/DH Edwin Encarnación, $60 million, 2017-19
• 1B/DH Josh Bell, $33 million, 2023-24

Best: Roberto Alomar

Cleveland traded Alomar to the Mets before the fourth and final year of this deal, but it sure got its money’s worth on the first three. Alomar was worth 20.3 bWAR for 1999 to 2001, named an All-Star and a Gold Glover in all three seasons. He also won a pair of Silver Sluggers and placed top four in the AL MVP vote in both ’99 and ’01.

Worst: Nick Swisher

Swisher’s first year in Cleveland was reasonably solid. He hit 22 home runs and was one of the most valuable players on the roster. But an injury-plagued second season was the beginning of the end for the outfielder who had eclipsed 20 home runs in nine consecutive seasons. He hit .208 in 2014 and .196 in 2015. After 2.5 years, Cleveland dumped both Swisher and Bourn to Atlanta—and made it to the World Series the year after doing so.

Every $25+ Million Contract

• LHP Mike Hampton, $121 million, 2001-08
• LHP Denny Neagle, $51 million, 2001-05
• OF Michael Cuddyer, $31.5 million, 2012-14
• OF Gerardo Parra, $27.5 million, 2016-18
• OF Ian Desmond, $70 million, 2017-21
• RHP Wade Davis, $52 million, 2018-20
• RHP Bryan Shaw, $27 million, 2018-20
• LHP Jake McGee, $27 million, 2018-20
• OF Kris Bryant, $182 million, 2022-28

Best: Michael Cuddyer

Most of these ended up being terrible for Colorado. (The jury is still out on Bryant’s contract, though it is definitely trending in a dreadful direction after two years.) But Cuddyer was a worthwhile investment. He did miss darn near half of the Rockies’ games from 2012 to ’14—and they finished at least 14 games below .500 in each of those seasons—but he hit .307/.362/.525 and received MVP votes in 2013.

Worst: The two pitchers signed in 2001

Credit to the Rockies for at least attempting to address the pitching woes that negated what was a sensational offense through the first eight years of the franchise’s existence. They threw a combined $172 million at Mike Hampton (NL Cy Young runner-up in 1999) and Denny Neagle (third place in NL Cy Young vote in 1997). But what an absolute disaster that was. Hampton lasted two years with a 5.75 ERA before getting traded to the Marlins. Neagle gave the Rockies a little over two years with a 5.57 ERA before his career ended. If forced to pick one, we’d have to go with Hampton, as he was more than twice as expensive. Quite the painful tandem signed within a week of each other, though.

Every $25+ Million Contract

• OF Magglio Ordonez, $75 million, 2005-09
• RHP Anibal Sanchez, $80 million, 2013-17
• 1B Prince Fielder, $214 million, 2012-20
• C/DH Victor Martinez, $64 million, 2015-18
• RHP Jordan Zimmermann, $110 million, 2016-20
• OF Justin Upton, $132.75 million, 2016-21
• LHP Eduardo Rodriguez, $77 million, 2022-26
• SS Javier Báez, $140 million, 2022-27
• Guys who signed contracts with Detroit worth $25-$50 million: Victor Martinez ($50M), Iván Rodríguez ($40M), Dean Palmer ($36M), Torii Hunter ($26M)

Best: Iván Rodríguez

“Pudge” was already well on his way to Cooperstown before he landed in Detroit, but he was great for the Tigers, who later picked up the club option for a fifth season on this deal. In each of the first four years, he was an All-Star, as well as a Gold Glove recipient in three of the four seasons. He hit .298, was worth 11.8 bWAR and helped get the Tigers into the 2006 World Series.

Worst: Jordan Zimmermann

Between Fielder and Upton, the Tigers have done one heck of a job of signing guys to massive contracts, only to trade them away right before they crashed and burned. (Miguel Cabrera extension notwithstanding.) But they did get stuck holding the bag with J-Zimm, who after several, durable, Cy Young-caliber seasons with the Nationals gave the Tigers a 5.63 ERA while making just 97 starts over the span of half a decade. (If we revisit this in a few years, though, Javier Báez is very much on track to take this dubious crown from Zimmermann.)

Every $25+ Million Contract

• LHP Andy Pettitte, $31.5 million, 2004-06
• OF Carlos Lee, $100 million, 2007-12
• RHP Scott Feldman, $30 million, 2014-16
• OF Josh Reddick, $52 million, 2017-20
• OF Michael Brantley, $32 million, 2019-20
• OF Michael Brantley, $32 million, 2021-22
• 1B Jose Abreu, $58.5 million, 2023-25
• RHP Rafael Montero, $34.5 million, 2023-25

Best: Andy Pettitte

Pettitte’s first and third years in Houston were nothing special, but he was masterful in 2005, making 33 starts with a 2.39 ERA, teaming with Roger Clemens and Roy Oswalt to anchor a rotation that made it to the World Series before getting swept by the White Sox. The Astros had consistently been a contender in the 1996 to 2004 timeframe, but it’s no coincidence that they finally made it to a Fall Classic in one of the best seasons of Pettitte’s career.

Worst: Rafael Montero

All six of the completed contracts worked out reasonably well for Houston. Lee was certainly overpaid by the end of his nine-figure deal, and the latter Brantley contract didn’t go nearly as well as the former. But there weren’t any immediate regrets. Except for maybe Montero, who had a fantastic 2022 campaign for the Astros that resulted in a three-year deal at the age of 32 with a career 4.64 ERA. He struggled mightily in 2023, though, and now might be getting paid eight figures to serve in a mop-up role for the next two years.

Every $25+ Million Contract

• RHP Gil Meche, $55 million, 2007-11
• OF José Guillén, $36 million, 2008-10
• RHP Jeremy Guthrie, $25 million, 2013-15
• LHP Jason Vargas, $32 million, 2014-17
• 2B Omar Infante, $30.25 million, 2014-17
• RHP Joakim Soria, $25 million, 2016-18
• OF Alex Gordon, $72 million, 2016-19
• RHP Ian Kennedy, $70 million, 2016-20

Best: Jason Vargas

Vargas missed most of 2015 and 2016 because of Tommy John surgery, but he pitched well while healthy, giving the Royals a 7.8 bWAR in his 74 games started. He made three October starts during their run to the 2014 World Series, and he was an All-Star in 2017. Can’t ask for much more than that from what averaged out to an $8 million salary.

Worst: José Guillén

$12 million per year for a 32-year-old, zero-time All-Star outfielder is a questionable investment for a mid-market franchise, even by 2023 standards. But for the small-market Royals in the late 2000s, Guillén’s contract was more than 15 percent of the total money spent for those three years. And he wasn’t even remotely worth it, giving them a negative-2.3 bWAR in what were the final three seasons of his career.

Every $25+ Million Contract

• 1B Mo Vaughn, $80 million, 1999-2004
• OF Vladimir Guerrero, $70 million, 2004-08
• OF Torii Hunter, $90 million, 2008-12
• LHP C.J. Wilson, $77.5 million, 2012-16
• 1B Albert Pujols, $240 million, 2012-21
• OF Josh Hamilton, $125 million, 2013-17
• 3B Anthony Rendon, $245 million, 2020-26
• Guys who signed contracts with Los Angeles worth $25-$60 million: Raisel Iglesias ($58M), Bartolo Colon ($51M), Gary Matthews Jr. ($50M), Tyler Anderson ($39M), Zack Cozart ($38M), Orlando Cabrera ($32M)

Best: Vladimir Guerrero

Most of these big contracts were horrendous for the Angels. But signing Guerrero was a rare W. He was the AL MVP in the first year of the deal, finished third in that vote in years No. 2 and 4 and got some votes in both years No. 3 and 5. He hit north of .300 in all five years, ending that half-decade at .323/.387/.558 with 158 home runs and 41 outfield assists.

Worst: Pick your favorite nine-figure disaster

The Mo Vaughn and Gary Matthews Jr. contracts were brutal for the Angels, but at least they were under $100 million. Spending a combined $610 million for Josh Hamilton, Albert Pujols and Anthony Rendon is more or less why this franchise completely wasted having both Mike Trout and Shohei Ohtani in recent years. At least Pujols was somewhat productive and at least there’s still a theoretical chance for Rendon to turn things around over the next three seasons. Hamilton gave them two pathetic seasons and then they paid him nearly $80 million to go to Texas. That may have been the ugliest of the ugly outcomes.

Every $25+ Million Contract

• RHP Kevin Brown, $105 million, 1999-2005
• RHP Zack Greinke, $147 million, 2013-18
• 3B Justin Turner, $64 million, 2017-20
• RHP Kenley Jansen, $80 million, 2017-21
• LHP Clayton Kershaw, $93 million, 2019-21
• RHP Trevor Bauer, $110 million, 2021-23
• 1B Freddie Freeman, $162 million, 2022-27
• Guys who signed contracts with Los Angeles worth $25-$60 million: Chris Taylor ($60M), Darren Dreifort ($55M), J.D. Drew ($55M), A.J. Pollock ($55M), Brandon McCarthy ($48M), Scott Kazmir ($48M), Rich Hill ($48M), Jason Schmidt ($47M), Manny Ramirez ($45M), Juan Pierre ($44M), Rafael Furcal ($39M), Andruw Jones ($36.2M), Derek Lowe ($36M), Justin Turner ($34M), Rafael Furcal ($30M), Joe Kelly ($25M)

Best: Zack Greinke

Greinke’s six-year, $147 million contract ended up only being a three-year, $70 million deal when he opted out of the final three years to sign his gigantic contract with the Diamondbacks. But the Dodgers sure were rewarded for their investment. Greinke made 92 regular-season starts with a 2.30 ERA, finishing top 10 for the NL Cy Young in all three years. (It is still absurd that he did not win the 2015 Cy Young, going 19-3 with a 1.66 ERA and 0.84 WHIP.) He also made six postseason starts for L.A., all of them quality starts.

Worst: Trevor Bauer

Fresh off winning the 2020 NL Cy Young, the Dodgers signed Bauer to a three-year, $110 million contract, making him one of the highest-salaried pitchers ever. And while he did give them a 2.59 ERA over 17 starts in the first three months of that contract, he hasn’t appeared in an MLB game since June 2021 following domestic violence allegations. The Dodgers were able to void a chunk of that contract while he was suspended, but SI‘s Tom Verducci reported last February that they ended up paying $61 million for those 17 starts. (One could certainly argue that paying Dreifort $55 million for 205.2 innings with a 4.64 ERA was even more detrimental on the field.)

Every $25+ Million Contract

• RHP Heath Bell, $27 million, 2012-14
• LHP Mark Buehrle, $58 million, 2012-15
• SS José Reyes, $106 million, 2012-17
• LHP Wei-Yin Chen, $80 million, 2016-20
• OF/DH Jorge Soler, $36 million, 2022-24
• OF Avisaíl García, $53 million, 2022-25

Best: Jorge Soler

To be clear, the Soler contract wasn’t anything special for the Marlins. He did hit 36 home runs this past season, but he was not productive in 2022 and opted out of the third year. All told, he was worth 2.2 bWAR for the Fish. But at least he was worth something on a team that made the postseason.

Worst: That entire free-spending experiment in 2012

In a vast ocean of seasons languishing near the bottom of the league in payroll, the Marlins randomly decided to spend a ton during the 2011-12 offseason, almost doubling their payroll while bringing in Heath Bell, Mark Buehrle and José Reyes on multiyear deals. But after a 93-loss season, they traded away all three (and more), immediately pulling the plug on that approach and not finishing within 15 games of first place in the NL East again until 2020. Reyes and Buehrle did at least play well during that one weird season in Miami, though.

Every $25+ Million Contract

• RHP Jeff Suppan, $42 million, 2007-10
• LHP Randy Wolf, $29.75 million, 2010-12
• 3B Aramis Ramírez, $36 million, 2012-14
• RHP Kyle Lohse, $33 million, 2013-15
• RHP Matt Garza, $50 million, 2014-17
• CF Lorenzo Cain, $80 million, 2018-22

Best: Aramis Ramírez

Giving this third baseman a three-year deal heading into his age-34 season was quite the risk taken by the Brewers, but it panned out reasonably well. He hit .300 with 50 doubles and finished ninth in the NL MVP vote in the first year of the contract, and he was an All-Star in year No. 3, hitting .288 and on a 162-game pace for 25 HR and 100 RBI in the first half of that campaign. They didn’t make the playoffs in any of those three years, though, so if you prefer Lorenzo Cain in this spot, I won’t argue with you.

Worst: Either Jeff Suppan or Matt Garza

Really tough call here. In both cases, the Brewers took a bit of a chance on a 30-something starting pitcher who had never been an All-Star and had never received a Cy Young vote. And both went miserably, each amounting to a negative-0.7 bWAR over the course of their four seasons in Milwaukee. Suppan and Garza did both have a decent first year with the Brewers, but the latter 75 percent of those contracts were painful.

Every $25+ Million Contract

• OF Kirby Puckett, $30 million, 1993-97
• RHP Ricky Nolasco, $49 million, 2014-17
• RHP Ervin Santana, $55 million, 2015-18
• 3B Josh Donaldson, $92 million, 2020-23
• SS Carlos Correa, $105.3 million, 2022-24
• SS Carlos Correa, $200 million, 2023-28
• C Christian Vázquez, $30 million, 2023-25

Best: Ervin Santana

Santana fell apart in the fourth year of this deal, but he was worth 10.4 bWAR in the first three seasons, including generating legitimate AL Cy Young consideration as a 34-year-old in 2017. He tossed three complete-game shutouts that year and carried what was otherwise a lackluster (to put it nicely) starting rotation in both 2016 and 2017.

(Honorable mention to Kirby Puckett, who played well for the first three years of that deal before the career-ending injury. But his contract is quite the testament to how much MLB salaries have ballooned in three decades. He finished second in the 1992 AL MVP vote, reached free agency and then re-signed with the Twins for $6 million per year—and was their highest-paid player in 1993, making 70 percent more than his closest teammate. Can’t even get a decent middle reliever for that price anymore.)

Worst: Ricky Nolasco

The Twins kind of had to sign Santana during the 2014-15 offseason, because their big pitching acquisition from the previous year was such a colossal disappointment. Nolasco made 57 appearances for Minnesota with a 5.44 ERA and 1.47 WHIP. The Twins did at least manage to trade the final 1.5 years of his contract to the Angels, but the main player they got for him (Héctor Santiago) was just as bad, making 26 appearances with a 5.61 ERA and 1.43 WHIP.

Every $25+ Million Contract

• OF Carlos Beltrán, $119 million, 2005-11
• OF Jason Bay, $66 million, 2010-13
• OF Yoenis Céspedes, $75 million, 2016-18
• OF Yoenis Céspedes, $110 million, 2017-20
• RHP Max Scherzer, $130 million, 2022-24
• OF Starling Marte, $78 million, 2022-25
• RHP Kodai Senga, $75 million, 2023-27
• RHP Justin Verlander, $86.7 million, 2023-24
• RHP Edwin Diaz, $102 million, 2023-27
• OF Brandon Nimmo, $162 million, 2023-30
• Guys who signed contracts with New York worth $25-$60 million: Curtis Granderson ($60M), Pedro Martinez ($53M), Billy Wagner ($43M), Kevin Appier ($42M), James McCann ($40.6M), Jay Bruce ($39M), Francisco Rodriguez ($37M), Oliver Perez ($36M), Tom Glavine ($35M), Robin Ventura ($32M), Jeurys Familia ($30M), Bobby Bonilla ($29M), Mark Canha ($26.5M), Cliff Floyd ($26M), Jose Quintana ($26M), Luis Castillo ($25M)

Best: Carlos Beltrán

It was the third-most expensive of New York’s 26 $25+ million contracts, but at least Beltrán delivered the goods. In his 6.5 seasons with the Mets, he was worth 31.1 bWAR and was rated by FanGraphs as the 11th-most valuable position player from 2005 to ’11. The switch-hitting center fielder was named an All-Star five times, an MVP vote recipient four times, a Gold Glover three times and a Silver Slugger twice.

Worst: Yoenis Céspedes

The Jason Bay contract has long been regarded as one of the most regrettable moves in MLB history, but the Mets may have out-done themselves when they signed Céspedes to his second, bigger contract. He was stellar in both 2015 and 2016, opting out of his first multiyear deal for an even larger one. But because of a litany of injuries, over the course of the latter four-year deal, he made an estimated $80.4 million to appear in 127 games.

Every $25+ Million Contract

• 1B Jason Giambi, $120 million, 2002-08
• 3B Álex Rodríguez, $275 million, 2008-17
• LHP CC Sabathia, $161 million, 2009-15
• 1B Mark Teixeira, $180 million, 2009-16
• RHP Masahiro Tanaka, $155 million, 2014-20
• OF Jacoby Ellsbury, $153 million, 2014-20
• RHP Gerrit Cole, $324 million, 2020-28
• OF Aaron Judge, $400 million, 2023-31
• LHP Carlos Rodón, $162 million, 2023-28
• Guys who signed contracts with New York worth $25-$100 million: D.J. LeMahieu ($90M), Mike Mussina ($88.5M), Bernie Williams ($87.5M), Aroldis Chapman ($86M), Brian McCann ($85M), A.J. Burnett ($82.5M), Jorge Posada ($52.4M), Johnny Damon ($52M), Chase Headley ($52M), Derek Jeter ($51M), Mariano Rivera ($45M), Carlos Beltran ($45M), Anthony Rizzo ($40M), Carl Pavano ($39.95M), Gary Sheffield ($39M), Zack Britton ($39M), Andrew Miller ($36M), Rafael Soriano ($35M), J.A. Happ ($34M), Anthony Rizzo ($32M), Mariano Rivera ($30M), Roger Clemens ($28M), Danny Tartabull ($25.5M)

Best: Mike Mussina

Gerrit Cole is rapidly trending in a direction to become the new No. 1 here, but we’re not quite ready to hand him the throne four seasons into his nine-year deal. So it goes to Mussina, who wasn’t actually named an All-Star in any of the six years on his $88.5 million deal, but who was just a solid B+ or A- pitcher for the duration of that contract. Per FanGraphs, “Moose” was the seventh-most valuable pitcher in the majors from 2001 to ’06, winning 92 of his 187 starts.

Worst: Jacoby Ellsbury

If Carlos Rodón’s next five years are anything like his first in pinstripes, it’ll go down as an all-time disaster of a signing. But, again, it’s too early to make that proclamation. Thus, Ellsbury remains the most regrettable big signing in Yankees history. He actually wasn’t that bad, at least in his first season. But between never even remotely approaching the phenom that he was for loathed Boston in 2011 and not even playing the final three years on the contract, Ellsbury will forever be the antithesis of a fan favorite in the Bronx.

Every $25+ Million Contract

• 1B Mark McGwire, $28 million, 1993-97
• OF Rubén Sierra, $28 million, 1993-97
• 1B/DH Billy Butler, $30 million, 2015-17

Best: Mark McGwire

“Big Mac” missed most of 1993 and 1994 with foot injuries, but there’s no question he was the most successful of these three candidates. Prior to getting traded to St. Louis in the summer of 1997, McGwire homered at a 162-game pace of 56.1 through the first 4.5 years of his contract, including leading the majors with 52 dingers in 1996.

Worst: Billy Butler

The lone time in the past three decades that Oakland decided to spend money on a free agent, it, uh, didn’t go well. Butler was fresh off a rough final season in Kansas City when the Moneyball A’s decided the 29-year-old who had a .298 batting average in his first seven seasons in the majors was the perfect buy-low candidate. However, Butler never did bounce back, released in September of the second season of his three-year deal.

Every $25+ Million Contract

• 1B Jim Thome, $85 million, 2003-08
• LHP Cliff Lee, $120 million, 2011-15
• OF/1B Bryce Harper, $330 million, 2019-31
• RHP Zack Wheeler, $118 million, 2020-24
• C J.T. Realmuto, $115.5 million, 2021-25
• OF Kyle Schwarber, $79 million, 2022-25
• OF Nick Castellanos, $100 million, 2022-26
• SS Trea Turner, $300 million, 2023-33
• Guys who signed contracts with Philadelphia worth $25-$75 million: Jake Arrieta ($75M), Taijuan Walker ($72M), Carlos Santana ($60M), Jonathan Papelbon ($50M), Andrew McCutchen ($50M), Jimmy Rollins ($38M), Raul Ibanez ($31.5M), Didi Gregorius ($28M), Carlos Ruiz ($26M)

Best: Zack Wheeler

Wheeler does have one more year left on this contract, but we’ve seen enough to declare this Philadelphia’s best free-agent signing. At least as far as FanGraphs is concerned, Wheeler has been the most valuable pitcher in the majors since the beginning of 2020, making 101 starts for the Phillies with a 3.06 ERA. And that doesn’t even account for how great he has been in the postseason, making 11 appearances with a 2.42 ERA.

Worst: Didi Gregorius

It was only $28 million, so you could easily make the case that Jake Arrieta’s $75 million contract was more detrimental to Philadelphia’s cause. But Gregorius sure did fool the Phillies by giving them a productive, fully healthy season in 2020 before re-signing for two more seasons and completely imploding. In the 166 games played in 2021 and 2022 before they cut him, Gregorius had an atrocious .613 OPS, hitting fewer home runs (14) than the number of errors he committed at shortstop (20).

Every $25+ Million Contract

• LHP Francisco Liriano, $39 million, 2015-17
• RHP Iván Nova, $26 million, 2017-19

Best: Iván Nova

It’s a good thing we included free agents who re-signed with the same team, or else Pittsburgh wouldn’t have had a player on the list. And between Nova and Liriano—neither of whom made it to the third season of their contract before getting traded away—Nova was slightly more productive and a good bit less expensive. It wasn’t great, though. He had nearly identical mediocre marks in both 2017 and 2018, giving the Pirates a 4.16 ERA and a 1.28 WHIP.

Worst: Francisco Liriano

The first year of Liriano’s deal was solid, posting a 3.38 ERA. Year No. 2 was a disaster, though. And when they finally decided they were done with him, they traded him, Reese McGuire and Harold Ramirez for Drew Hutchison, who logged just 11.1 innings for the Pirates. At least with Nova, the expectations were never particularly high. Liriano, however, was a Cy Young candidate in previous healthy seasons, including one with Pittsburgh in 2013. He just never got back to that level after his big payday.