We’ve seen plenty of large contracts in recent years -- both for free agents and teams extending players already on their roster. Here’s a look at each team’s largest free-agent contract and biggest extension by total value, along with the season that it was signed either during or entering, and the amount added to the deal in the cases of extensions.
AMERICAN LEAGUE EAST
FA contract: George Springer, OF (6 years/$150M, 2021)
Extension: Vernon Wells, OF (7/$126M, 2007)
The Blue Jays’ latest big offseason addition set a record for total value, surpassing Russell Martin’s $82 million deal, which was the prior largest for a Toronto-bound free agent. Wells never played out the entirety of his extension, which ran through 2014, in Toronto, as he was traded to the Angels in January 2011 and to the Yankees in March 2013.
FA contract: Chris Davis, 1B (7/$161M, 2016)
Extension: Adam Jones, OF (6/$85M, 2012)
After three and a half seasons with the Rangers and four and a half with the Orioles, Davis hit free agency following a 2015 season where he crushed 47 homers to lead the Majors. He tested free agency, but he still re-upped with the Orioles. Jones, on the other hand, got his extension during the season in 2012 -- a year he’d go on to finish sixth in the AL MVP voting, the highest finish of his career.
FA contract: Zach Eflin, RHP (3/$40M, 2023)
Extension: Wander Franco (11/$182M, 2022)
Franco’s contract -- which includes a 12th-year club option and can max out at $223 million -- represents the largest deal of any kind in Rays history, topping the six-year, $100 million extension Evan Longoria signed after the 2012 season. Eflin's deal broke a longstanding record for the largest free-agent contract in Rays history. The previous mark belonged to Wilson Alvarez, who signed a five-year, $35 million deal before the Rays franchise had played a game.
FA contract: David Price, LHP (7/$217M, 2016)
Extension: Rafael Devers (11/$331M, 2023)
At the time, Price’s deal was the largest by total value for a pitcher. He didn’t play out the entire contract in Boston following a February 2020 trade to the Dodgers. Devers' $331 million extension surpassed Price's deal for the largest Red Sox contract of any kind and Adrián González's seven-year, $154 million contract signed in 2011 as the franchise's largest extension.
FA contract: Aaron Judge, OF (9/$360M, 2023)
Extension: Derek Jeter, SS (10/$189, 2001)
Hitting the open market after setting an AL record with 62 homers and winning the AL MVP Award in 2022, Judge received serious overtures from the hometown Giants but ultimately returned to the Yankees, reaching the largest free-agent deal in MLB history. Jeter’s extension helped ensure that the Hall of Famer would play his entire career in pinstripes. When the extension was over, he signed one more deal with the Yankees in free agency, retiring at the end of that contract in 2014.
FA contract: Edwin Encarnación, 1B/DH (3/$60M, 2017)
Extension: José Ramírez, 3B (5/$124M, 2022)
Ramírez’s extension – which came ahead of his 10th season in Cleveland – more than doubled Encarnación’s deal, previously the largest by total value in franchise history. As part of the agreement, Cleveland has exercised Ramírez’s $13 million team option for 2023. The extension will kick in after that, keeping the third baseman with the club through 2028. Encarnación played the first two years of his deal with the Guardians before he was traded to the Mariners in a three-team deal that also involved the Rays. During his time in Cleveland, he put up two 30-homer seasons.
FA contract: Alex Gordon, OF (4/$72M, 2016)
Extension: Salvador Perez (4/$82M, 2021)
It seems hard to imagine now, but there was a point when it wasn’t a given that Gordon would be a Royal for life. When he hit free agency after the 2015 season, he was a newly minted World Series champion and had been an All-Star in three straight years. He eventually re-signed with Kansas City, signed one last deal entering 2020 and then hung up his cleats after the season. Perez is another Royals lifer, and his $82 million extension is set to begin in 2022, a year after he led the Majors in homers (48) and RBIs (121).
FA contract: Prince Fielder, 1B (9/$214M, 2012)
Extension: Miguel Cabrera, 1B (8/$248M, 2014)
Fielder was on the heels of a third-place NL MVP finish when he signed with the Tigers for the 2012 season. He was traded to the Rangers after the first two years of the deal, but a neck injury forced Fielder to step away in 2016 after he was not cleared medically. The Marlins traded Cabrera to the Tigers in December 2007, and he signed his extension after back-to-back MVP seasons.
FA contract: Carlos Correa, SS (6/$200M, 2023)
Extension: Joe Mauer, C (8/$184M, 2010)
Correa's agreement in January 2023 topped his $105.3 million deal with the Twins from the previous year as the franchise's largest for a free agent. That three-year pact contained opt-outs after each of the first two years, which Correa exercised following the 2022 season. However, his journey on the open market was a wild one, featuring reported deals with the Giants and Mets that fell through due to apparent medical concerns. That allowed the Twins to get back into the sweepstakes and bring back the star shortstop. Mauer’s contract is the largest by total value for a catcher, and it ensured that the only line on the St. Paul, Minn., native’s transaction file reads: drafted first overall by the Twins in the 2001 MLB Draft.
FA contract: Andrew Benintendi, OF (5/$75M, 2022)
Extension: Yoán Moncada, 3B (5/$70M, 2020)
The White Sox reached an agreement with Benintendi to fill a corner outfield need as well as the need for a solid left-handed bat in a predominantly right-handed lineup. Moncada had a breakout season in 2019, his third year with the White Sox after arriving from Boston in the Chris Sale trade, and got his extension the following spring.
FA contract: Anthony Rendon, 3B (7/$245M, 2020)
Extension: Mike Trout, OF (10/$360M, 2019)
After winning a World Series title with the Nationals, the ever-consistent Rendon joined the Angels and continued at the same level he’d been playing at since 2017 in his first year before dealing with injuries in 2021. Trout’s deal was added on to an existing two years and $66.5 million he had left on his prior extension, so the full contract is for 12 years and $426.5 million, which was the largest in North American professional sports at the time it was signed.
FA contract: Carlos Lee, 1B/LF (6/$100M, 2007)
Extension: Jose Altuve, 2B (5/$151M, 2018)
Lee played the first five and a half years of the contract with the Astros, winning a Silver Slugger Award in his first year in 2007, when he also got an All-Star nod. In July 2012, the Astros traded him to the Marlins, where he finished off the final months of the deal. The Astros have the 2017 AL MVP under contract through 2024, which he inked just months after winning the World Series.
FA contract: Billy Butler, 1B/DH (3/$30M, 2015)
Extension: Eric Chavez, 3B (6/$66M, 2004)
Butler signed with the A’s after spending the first eight years of his career in Kansas City. After 236 games with the club in 2015-16, the A’s released him in September 2016 before the deal’s second year was over. Oakland extended Chavez before the 2004 season, on the heels of three straight Gold Glove Awards. He played out the duration of the contract before joining the Yankees and D-backs on smaller deals to finish his career. The A’s also signed Yoenis Céspedes to a four-year, $36 million deal, but that is not noted above as it was an international signing, not via traditional free agency.
FA contract: Robinson Canó, 2B (10/$240M, 2014)
Extension: Julio Rodríguez, CF (13/$210M, 2022)
Canó spent the first nine years of his career with the Yankees before joining the Mariners in free agency following four straight top six MVP finishes, Silver Slugger Awards and All-Star selections. The Mariners traded him and Edwin Díaz in a deal to the Mets after the fifth year of the deal. Rodríguez's extension guarantees 13 years and $210 million, but could max out at 18 years and $470 million. The team's prior largest extension belonged to Félix Hernández, another Seattle icon, like Rodríguez has quickly become.
FA contract: Corey Seager, SS (10/$325M, 2022)
Extension: Elvis Andrus, SS (8/$120M, 2013)
Nearly 20 years after signing Alex Rodriguez to a 10-year, $252 million deal, the largest by total value at the time, the Rangers struck again to add another star shortstop, reaching a 10-year, $325 million contract with Seager. Andrus, Texas' starting shortstop until he was traded to the A's in 2021, had played four full seasons at the time of his extension, including a second-place Rookie of the Year finish in his first year in 2009.
NATIONAL LEAGUE EAST
FA contract: B.J. Upton, OF (5/$75.25M, 2013)
Extension: Austin Riley, 3B (10/$212M, 2022)
Upton played the first two years of his deal with the Braves before an offseason trade to the Padres. After a season in San Diego, the Padres traded him to the Blue Jays in July 2016. Riley took the baton from departed first baseman Freddie Freeman with the largest extension, and largest deal, in Braves history. Riley's deal, signed in August 2022, runs through 2032 with an option year for 2033.
FA contract: José Reyes, SS (6/$106M, 2012)
Extension: Giancarlo Stanton, OF (13/$325M, 2015)
Reyes, a reigning batting champ at the time, was part of a group of stars the Marlins signed entering the 2012 season, when they were rebranding and opening Marlins Park. In November 2012 after a year in Miami, he was traded to the Blue Jays in a deal involving 12 players. At the time it was signed, Stanton’s contract was the largest by total value in baseball history, and it’s still tied for the longest contract by years. Stanton was traded to the Yankees after the 2017 season.
FA contract: Carlos Beltrán, OF (7/$119M, 2005)
Extension: Francisco Lindor, SS (10/$341M, 2021)
Lindor's extension came before he'd even played a game in a Mets uniform, after a January 2021 trade from Cleveland to New York. The extension, which kicks in during the 2022 season -- meaning Lindor will be in Flushing for 11 years -- is the third-largest contract by total value in baseball history. Beltrán’s Mets tenure was the most productive of his career by certain measures -- his 149 homers and .500 slugging percentage were each his highest with any team. The Mets traded him to the Giants in July 2011, the final year of his deal, for Zack Wheeler.
FA contract: Stephen Strasburg, RHP (7/$245M, 2020)
Extension: Strasburg (7/$175M, 2016)
Nationals fans should be unsurprised to learn that Strasburg holds both spots on this list. The No. 1 overall pick in the 2009 MLB Draft signed his lucrative extension during the season in 2016, with the deal first reported while he was on the mound in a game and made official the next day. The contract had an opt-out after the 2019 season, which Strasburg took -- days after winning the World Series MVP Award as the Nats won the title in seven games. He re-upped with the Nationals in free agency, signing the franchise’s largest such deal.
FA contract: Bryce Harper, OF (13/$330M, 2019)
Extension: Cole Hamels, LHP (6/$144M, 2012)
At the time, Harper’s contract set a record largest free-agent deal in MLB history. The previous Phillies free-agent record was the $120 million deal signed by Cliff Lee after the 2010 season. Hamels’ contract was the second largest for a pitcher at the time, as well as the largest extension for a pitcher. The Phillies traded him to the Rangers in July 2015 -- his final start with the Phils was a no-hitter at Wrigley Field.
FA contract: Lorenzo Cain, OF (5/$80M, 2018)
Extension: Christian Yelich, OF (7/$188.5M, 2020)
After spending seven years with the Royals and winning the 2015 World Series, Cain rejoined the Brewers as a free agent -- the team he’d been drafted by in 2004 and debuted with in '10 before being part of a trade to Kansas City for Zack Greinke. For Yelich, the contract extension came after two straight MVP-level seasons in Milwaukee after a trade from the Marlins. The slugger won the 2018 award and finished second to the Dodgers' Cody Bellinger in '19.
FA contract: Matt Holliday, OF (7/$120M, 2010)
Extension: Paul Goldschmidt, 1B (5/$130M, 2019)
The A’s traded Holliday to the Cardinals in July 2009, when he was months shy of free agency. After hitting .353 in 63 regular-season games with St. Louis after the trade, he signed with the team as a free agent. Goldschmidt also arrived in a trade from a West team, when the D-backs sent him to St. Louis in December 2018. Before Goldschmidt had even played a regular-season game for the club, the Cardinals ensured they’d have him through the 2024 season with an extension.
FA contract: Jason Heyward, OF (8/$184M, 2016)
Extension: Carlos Zambrano, RHP (5/$91.5M, 2007)
The Cubs signed Heyward after a year with the division-rival Cardinals where he received MVP votes and won a Gold Glove Award. The move to Chicago paid off for him and the team immediately, as the club won the World Series in his first year with the Cubs in 2016 during a postseason run where his defense was a notable contribution. When the Cubs extended Zambrano in August 2007, he was in the midst of his third Cy Young vote-worthy season. Ultimately, the club traded him to the Marlins after the 2011 season, when he was entering the final year of the deal.
FA contract: Francisco Liriano, LHP (3/$39M, 2015)
Extension: Bryan Reynolds, OF (8/$106.75M, 2023) (source)
Less than 13 months after Ke’Bryan Hayes signed what was the richest deal in Pirates history at $70 million over eight years, Reynolds topped it with his eight-year, $106.75 million contract (per a source). Reynolds, who joined the Pirates in the 2018 trade that sent franchise icon Andrew McCutchen to San Francisco, would have been eligible for free agency after the 2025 season. The Pirates’ largest free-agent contract was signed by Liriano following the 2014 campaign. The deal was Liriano’s second with the Pirates, after initially signing a two-year contract entering the 2013 season. He did not play out the latter contract in Pittsburgh, instead being traded to the Blue Jays during the 2016 season.
FA contract: Nick Castellanos/Mike Moustakas (4/$64M, 2020)
Extension: Joey Votto, 1B (10/$225M, 2012)
The Reds’ most lucrative free-agent contract by total value is a tie between two deals signed within two months of each other. In December 2019, the team added Castellanos on a four-year, $64 million pact before adding Moustakas for the same terms in January 2020. The largest extension, and overall contract, belongs to the team’s current franchise player and MVP winner in Votto, who has hit more than 300 home runs in a Reds uniform -- the only one he’s ever worn.
FA contract: Zack Greinke, RHP (6/$206.5M, 2016)
Extension: Corbin Carroll, OF (8/$111M, 2023)
Greinke opted out of a contract with the Dodgers in favor of free agency after the 2015 season, signing with the D-backs in a somewhat unexpected move at the time. After an uncharacteristic first season in Arizona, he returned to his All-Star ways over the next three years before he was traded to the Astros at the Trade Deadline in 2019. Carroll had just 38 days of MLB service time when he agreed to his deal, but the D-backs evidently saw enough from the highly touted prospect to guarantee him $111 million. Carroll's deal exceeded catcher Miguel Montero's $60 million pact (signed in 2012), which was previously the largest extension in D-backs history.
FA contract: Freddie Freeman (6/$162M, 2022)
Extension: Mookie Betts, OF (12/$365M, 2020)
Betts’ extension was the next step after a February 2020 trade sent the 2018 AL MVP winner from the Red Sox to the Dodgers, and he signed it before the ‘20 season began. The Dodgers added another former MVP Award winner when they signed Freeman (the '20 NL MVP) to a six-year deal in free agency after the '21 season. The move was a surprise for the first baseman, who was widely expected to return to the Braves after spending his first 12 seasons with the team and helping Atlanta win a World Series title in '21.
FA contract: Johnny Cueto, RHP (6/$130M, 2016)
Extension: Buster Posey, C (8/$167M, 2013)
After 7 1/2 years in Cincinnati and a half-season with the Royals that led to a World Series title, Cueto joined the Giants in free agency and immediately turned in a strong season, receiving MVP and Cy Young votes, as well as an All-Star selection. His frequent batterymate, Posey, received his extension after he followed up his 2010 Rookie of the Year Award with an MVP in 2012. Posey was the catcher on all three World Series-winning teams for the Giants in 2010, ‘12 and ‘14.
FA contract: Manny Machado, 3B (10/$300M, 2019)
Extension: Machado (11/$350M, 2023)
The Padres' signing of Machado in free agency came a year after the team added Eric Hosmer on a eight-year, $144 million deal, signaling that A.J. Preller and company were preparing for a new era of baseball in San Diego. Machado's contract gave him the ability to opt out at the end of 2023, but he signed an 11-year extension that will keep him in a Padres uniform through 2033. Machado's new $350 million deal topped the 14-year, $340 million pact Fernando Tatis Jr. signed in 2021 for the largest extension and overall contract in franchise history.
FA contract: Kris Bryant, OF (7/$182M, 2022)
Extension: Nolan Arenado, 3B (7/$234M, 2019)
The Rockies entered the spring of 2022 looking to add a big bat into the middle of their lineup. They found it in Bryant, a former MVP and four-time All-Star who had spent his first six full seasons with the Cubs before ending 2021 in the NL West with the Giants. Although injuries sapped Bryant's power in 2018 and 2020, he rebounded in 2021 by slamming 25 homers and posting a 124 OPS+ The move for the 30-year-old Bryant, a longtime third baseman, came a little more than a year after Colorado traded star third baseman to Nolan Arenado to the Cardinals.