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: Wilson Alvarez, LHP (5/$35M, 1998)
Extension: Evan Longoria, 3B (6/$100M, 2013)
Amazingly, Alvarez signed his deal before the Rays franchise had played a game. The average annual value of his deal has been topped many times by Rays free agents, but not the total value. Meanwhile, Longoria never played out his deal with Tampa Bay after he was traded to San Francisco prior to the 2018 season.
FA contract: David Price, LHP (7/$217M, 2016)
Extension: Adrián González (7/$154M, 2011)
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. Trades to the Dodgers are actually a theme here, as González was also traded there partway into his deal during the 2012 season.
FA contract: Gerrit Cole, RHP (9/$324M, 2020)
Extension: Derek Jeter, SS (10/$189, 2001)
Cole’s contract set numerous records, including the most total value on any contract for a pitcher and the highest average annual value on any contract at $36 million. 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: Travis Hafner, 1B/DH (4/$57M, 2007)
Encarnación played the first two years of his deal with the Indians 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. Hafner’s extension kept him with the Indians through the 2012 season, at which point he signed a one-year deal in '13 with the Yankees, where he finished his career.
FA contract: Alex Gordon, OF (4/$72M, 2016)
Extension: Danny Duffy, LHP (5/$65M, 2017)
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. Duffy is another Royals lifer -- at least so far -- and his contract runs through the 2021 season.
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: Josh Donaldson, 3B (4/$92M, 2020)
Extension: Joe Mauer, C (8/$184M, 2010)
After missing much of the 2018 season due to injury, Donaldson signed a one-year deal with the Braves for 2019 and played like the MVP candidate he’d been in the past. A Twins team that had just set a single-season club homer record added him for the 2020 season in a deal that is ongoing. 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: Yasmani Grandal, C (4/$73M, 2020)
Extension: Yoán Moncada, 3B (5/$70M, 2020)
After Grandal took a one-year bet on himself with a deal in Milwaukee for 2019, the White Sox inked him to the long-term deal he was seeking for 2020 and beyond. 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, if not before, in his first year. 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: Félix Hernández, RHP (7/$175M, 2013)
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. Hernández’s extension kept him in Seattle through the 2019 season, at which point the 15-year veteran pitched an emotional "goodbye" game during the final homestand of the year.
FA contract: Alex Rodriguez, SS (10/$252M, 2001)
Extension: Elvis Andrus, SS (8/$120M, 2013)
After spending his first seven years in Seattle, Rodriguez signed a $252 million deal with the Rangers, the largest by total value at the time. Texas traded him to the Yankees after three years, where he later opted out and re-signed, setting another contract record. Andrus 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: Freddie Freeman, 1B (8/$135M, 2014)
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. It’s fitting that the largest extension, and largest deal, in Braves history belongs to Freeman, the team’s next franchise-level star after Chipper Jones. The reigning NL MVP is signed through 2021.
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: David Wright, 3B (8/$138M, 2013)
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. When Wright signed his extension in December 2012, he was coming off the second-best season of his career by WAR and entering his age-30 season. Ultimately, he had to stop playing due to injury after the 2018 season.
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 franchise’s first No. 1 overall pick in the 2009 MLB Draft. He 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)
Harper’s contract set records for both the longest deal and most money given to a free agent, with the length tying Stanton’s extension for any contract. The prior largest free-agent deal the Phillies had handed out was $120 million to Cliff Lee. 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: Andrew McCutchen, OF (6/$51.5M, 2012)
This deal was Liriano’s second with the Pirates, after initially signing a two-year contract entering the 2013 season. After a 3.20 ERA in 55 starts during that span, he re-signed with the club after 2014, but he did not play all three years in Pittsburgh, instead being traded to the Blue Jays during the 2016 season. The Pirates extended McCutchen entering the 2012 season -- a year before he’d win the NL MVP Award -- after his first three seasons in the Majors. The team traded him to the Giants entering the final year of his deal in January 2018, and he was traded to the Yankees during that 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 almost 300 home runs in a Reds uniform -- the only one he’s ever worn.
FA contract: Zack Greinke, RHP (6/$206.5M, 2016)
Extension: Miguel Montero, C (5/$60M, 2012)
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. When Montero signed his extension during the season in 2012, he was on the heels of a 2011 season where he was a first-time All-Star and received MVP votes. The D-backs traded him to the Cubs after the 2014 season, where he helped the team win the World Series in ‘16.
FA contract: Zack Greinke, RHP (6/$147M, 2013)
Extension: Mookie Betts, OF (12/$365M, 2020)
Greinke has the unique position of holding the largest free-agent contract distinction for both the D-backs and the Dodgers. His contract in Los Angeles came first, when he signed with the team entering the 2013 season, and he proceeded to post a 2.30 ERA in 92 starts for the Dodgers over three years before opting out. 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. That gives Betts more than 10 years to become the second player to win MVP honors in both leagues.
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: Fernando Tatis Jr., SS (14/$340M, 2021) -- per source
The Padres' signing of Machado came a year after the team added Eric Hosmer in a eight-year, $144 million deal, signaling that A.J. Preller and company were preparing for the current Padres era we are now witnessing. But San Diego was not done committing big dollars to the left side of its infield. As Spring Training began in 2021, the club reached an agreement on a long-term deal with Tatis, less than two months after his 22nd birthday. In his first 143 MLB games split between 2019-20, Tatis already had established himself as one of the game's brightest stars, winning a Silver Slugger Award and finishing fourth in the NL MVP race in '20.
FA contract: Mike Hampton, LHP (8/$121M, 2001)
Extension: Nolan Arenado, 3B (7/$234M, 2019)
After a season with the Mets following a trade from the Astros, Hampton joined the Rockies in free agency and made the second All-Star Game of his career. He posted an ERA above 5.00 in each of his two seasons in Colorado before the team traded him to the Braves in 2002. After drafting Arenado in the second round of the 2009 MLB Draft, the third baseman has won a Gold Glove Award in each season of his career and had received MVP votes in four straight years at the time of his extension, which was signed in February 2019.