Grading Every MLB Team's Most Expensive Free-Agent Signing in History
The past two MLB offseasons have seen Shohei Ohtani and Juan Soto sign record-shattering deals of $700 million and $765 million, respectively, and while there is no payday of that caliber on the horizon this winter, we've already seen one huge signing.
Dylan Cease joined the Blue Jays on a seven-year, $210 million deal that stands as the largest free-agency addition in club history, and that serves as the perfect jumping-off point to dig into each team's largest free-agency deal.
Ahead, we've highlighted each team's most expensive free-agent signing based on total value of the contract, and given a grade to the signing based on individual production, role in team success and any potential trades that factored in before the deal was over.
Contract extensions were not considered, and to focus exclusively on outside additions, players who became free agents and then re-signed with their previous teams were also excluded. As a result, you will not find Chris Davis (BAL), Alex Gordon (KC), Carlos Correa (MIN), Aaron Judge (NYY), Francisco Liriano (PIT) and Matt Holliday (STL) in the following article, though they technically signed the largest free-agency deals in their respective club's history.
AL East
1 of 6
Baltimore Orioles: SS Miguel Tejada (2004)
Contract: 6 years, $72 million
Coming off a four-year run in Oakland where he averaged 31 home runs, 116 RBI and 4.7 WAR while winning 2002 AL MVP, Tejada was one of the biggest names in his free-agent class. He made three straight All-Star teams after joining the O's, racking up an AL-leading 150 RBI in his debut. After the fourth year of his contract, he was traded to the Astros for a package of five players.
Grade: B
Boston Red Sox: LHP David Price (2016)
Contract: 7 years, $217 million
The Red Sox signed Price to what was at the time the largest total money contract ever given to a pitcher, and while his four seasons in Boston were a mixed bag, his role on the 2018 World Series champs made it a success. He went 3-1 with a 3.46 ERA over 26 innings during the 2018 postseason, and logged quality starts in Game 2 and Game 5 of the World Series. The Red Sox ultimately shipped him to the Dodgers as a salary dump in the Mookie Betts blockbuster.
Grade: B
New York Yankees: RHP Gerrit Cole (2020)
Contract: 9 years, $324 million
Through his first six years with the Yankees, Cole has gone 59-28 with a 3.12 ERA, 1.03 WHIP and 915 strikeouts in 759 innings, and he finally won a long-awaited Cy Young in 2023. However, he made just 17 starts in 2024 and then spent the entire 2025 season sidelined following Tommy John surgery that is also expected to make him unavailable for 2026 Opening Day. He needs to win a ring to secure his legacy in the Bronx.
Grade: C
Tampa Bay Rays: RHP Zach Eflin (2023)
Contract: 3 years, $40 million
Eflin finished sixth in 2023 AL Cy Young voting, going 16-8 with a 3.50 ERA and 186 strikeouts in 177.2 innings in his Rays debut. As is often the case, the front office backloaded his deal, with an $11 million salary over the first two years and $18 million for the third. It then traded him midway through the second year, bringing back a package of three prospects.
Grade: B
Toronto Blue Jays: RHP Dylan Cease (2026)
Contract: 7 years, $210 million
The Blue Jays struck first on this year's pitching market, paying a pretty penny for Cease's swing-and-miss stuff, despite a good-not-great contract year where he posted a 4.55 ERA, 1.33 WHIP and 215 strikeouts in 168 innings. It is the seventh-largest total payday given to a pitcher, matching the $210 million contracts of Max Scherzer and Corbin Burnes.
Grade: Incomplete
AL Central
2 of 6
Chicago White Sox: OF Andrew Benintendi (2023)
Contract: 5 years, $75 million
At this point, Benintendi is serving the purpose of helping keep the White Sox payroll high enough that Major League Baseball does not start hassling them to spend more. Aside from that, he has managed just 0.6 WAR in 402 games over the first three years of his deal.
Grade: D
Cleveland Guardians: DH Edwin Encarnación (2017)
Contract: 3 years, $60 million
Encarnación provided his power production in 2017 (.881 OPS, 38 HR, 107 RBI) and 2018 (.810 OPS, 32 HR, 107 RBI) before he was traded to the Mariners in a three-team deal that reunited Cleveland with Carlos Santana. He didn't prove to be the missing piece for a team that reached the World Series the year before he was signed, but he produced up to expectations.
Grade: B
Detroit Tigers: 1B Prince Fielder (2012)
Contract: 9 years, $214 million
In hindsight, it's hard to believe Fielder only spent two seasons with the Tigers, joining Miguel Cabrera to form a dynamic one-two punch in 2012 (.940 OPS, 30 HR, 108 RBI) and 2013 (.819 OPS, 25 HR, 106 RBI). After two years, he was traded to the Rangers along with $30 million in exchange for Ian Kinsler, who went on to log three straight 5-WAR campaigns in Detroit.
Grade: B
Kansas City Royals: RHP Ian Kennedy (2016)
Contract: 5 years, $70 million
Kennedy lived up to his contract in his first season in Kansas City with a 3.68 ERA over 195.2 innings, but he struggled the next two years before shifting to the bullpen. That resulted in a career renaissance, as he logged 30 saves over 63 appearances in 2019, but he closed out the contract with a 9.00 ERA in 15 games during the abridged 2020 campaign.
Grade: D
Minnesota Twins: 3B Josh Donaldson (2020)
Contract: 4 years, $92 million
After a stellar one-year run with the Braves, Donaldson cashed in with a four-year deal, despite the fact that he was entering his age-34 campaign. Injuries limited him to 28 games in 2020, and when he bounced back with 26 home runs and 3.0 WAR in 135 games the following year, the Twins sold high and traded him to the Yankees for Gary Sanchez and Gio Urshela. The signing looked like a bad idea from the start, but they successfully cut their losses.
Grade: C
AL West
3 of 6
Athletics: RHP Luis Severino (2025)
Contract: 3 years, $67 million
The signing was a direct result of the tight-fisted Athletics trying to avoid a grievance from the MLBPA due to their lack of spending. Severino threw the ball well on the road (14 GS, 3.02 ERA, 80.1 IP), but struggled mightily in the team's temporary home in Sacramento (15 GS, 6.01 ERA, 82.1 IP). He could be on the move this winter.
Grade: Incomplete
Houston Astros: OF Carlos Lee (2007)
Contract: 6 years, $100 million
Lee hit the open market coming off four straight 30-homer seasons and back-to-back All-Star selections, and the Astros added him to a lineup that already featured Lance Berkman and Hunter Pence. Over his five full seasons in Houston, he hit .286/.338/.486 while averaging 26 home runs and 101 RBI, but during that time the Astros went from fringe contender to full-scale rebuild. He did not play a single postseason game in Houston.
Grade: C
Los Angeles Angels: 3B Anthony Rendon (2020)
Contract: 7 years, $245 million
Will this go down as the worst signing in MLB history? Rendon racked up 2.2 WAR in 52 games during the shortened 2020 season, but in five years since that solid Angels debut, he has played in a grand total of 205 games and tallied 1.7 WAR. The discussion has turned to a potential buy out ahead of the final year of his contract as he is expected to retire.
Grade: F
Seattle Mariners: 2B Robinson Canó (2014)
Contract: 10 years, $240 million
Canó hit .296/.353/.472 with 107 home runs and 23.9 WAR over five seasons in Seattle, but a PED suspension in 2018 tainted his accomplishments. That offseason, he was shipped to the Mets along with closer Edwin Díaz in a blockbuster deal, and he was hit with a year-long PED suspension in 2021. He did nab three All-Star selections and a pair of top-10 finishes in AL MVP voting during his time in Seattle, but he did not end up being the face of the franchise as expected.
Grade: D
Texas Rangers: SS Corey Seager (2022)
Contract: 10 years, $325 million
Regardless of how things unfold over the final six years of his contract, Seager has already established himself as an all-time great in Rangers history. He has racked up 22.1 WAR over four seasons, and he won 2023 World Series MVP honors while helping lead the club to its first-ever title. Even playing only 102 games in 2025, he was still a 6.2-WAR player and has shown no signs of slowing down heading into his age-32 campaign.
Grade: A
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NL East
4 of 6
Atlanta Braves: OF B.J. Upton (2013)
Contract: 5 years, $75.25 million
A talented but flawed player even at his best in Tampa Bay, Upton reached free agency after a 2012 season where he had a .298 on-base percentage and 169 strikeouts in 146 games, but that didn't stop the Braves from opening their wallets. He ended up hitting .198 with negative-1.7 WAR in 267 games in Atlanta over two seasons before he was attached to Craig Kimbrel and dumped on the Padres.
Grade: F
Miami Marlins: SS José Reyes (2012)
Contract: 6 years, $106 million
Reyes won the NL batting title (.337 BA) while swiping 39 bases and scoring 101 runs in his final season with the Mets, and the Marlins signed him as part of a spending spree to usher in their new stadium that also included adding Mark Buehrle and Heath Bell. All three players were gone a year later following a 69-93 finish, with Reyes and Buehrle both shipped to the Blue Jays as part of a massive 12-player blockbuster deal.
Grade: D
New York Mets: OF Juan Soto (2025)
Contract: 15 years, $765 million
A year after Shohei Ohtani signed a $700 million deal with significant deferred money, Soto topped it with a $765 million payday and no deferrals. Despite a heavily scrutinized slow start, he still ended up hitting .263/.396/.525 with 43 home runs, 105 RBI and a career-high 38 steals in a 6.2-WAR season. Still only 27 years old, he is on a Hall of Fame trajectory and will be the face of the franchise for the next decade.
Grade: Incomplete
Philadelphia Phillies: 1B/OF Bryce Harper (2019)
Contract: 13 years, $330 million
Harper has now spent the same number of seasons with the Phillies as he did with the Nationals at the start of his career, and he has added three Silver Sluggers, two All-Star selections and 2021 NL MVP honors during his time in Philadelphia. A World Series title is still the missing piece of the puzzle, and with an aging core, the Phillies window is starting to close. Is Harper still an elite-level star?
Grade: B
Washington Nationals: RHP Max Scherzer (2015)
Contract: 7 years, $210 million
Scherzer belongs squarely in the conversation alongside Greg Maddux to the Braves, Randy Johnson to the D-backs, Manny Ramirez to the Red Sox and Barry Bonds to the Giants for the title of best free-agent signing in MLB history. He won two Cy Young Awards and finished in the top 10 in balloting four other times over the life of the contract, also helping deliver a World Series title in 2019 and bringing back top prospects Keibert Ruiz and Josiah Gray on his way out the door in 2021.
Grade: A
NL Central
5 of 6
Chicago Cubs: OF Jason Heyward (2016)
Contract: 8 years, $184 million
A pair of Gold Glove Awards, 9.1 WAR and one legendary rain delay speech during Game 7 of the 2016 World Series are not enough to call the Heyward signing a successful move by the Cubs front office. He hit just .245 with an 85 OPS-plus during his time with the team, and after logging negative-0.6 WAR over 48 games in 2022 he was released ahead of the final year of his contract.
Grade: D
Cincinnati Reds: OF Nick Castellanos/3B Mike Moustakas (2020)
Contract: 4 years, $64 million
The Reds signed these two sluggers to matching deals during the 2019-20 offseason. Castellanos had a decent first season and hit .309/.362/.576 with 34 home runs and 100 RBI in his second year before exercising an opt-out clause and walking in free agency. Moustakas lasted three years and hit .216 with negative-1.8 WAR in 184 games before he was released.
Castellanos Grade: B
Moustakas Grade: F
Milwaukee Brewers: OF Lorenzo Cain (2018)
Contract: 5 years, $80 million
Cain emerged as one of the stars for a Royals team that reached back-to-back World Series in 2014 and 2015, then cashed in when he reached free agency after the 2017 season. He logged 6.8 WAR in his Brewers debut and won a Gold Glove the following year, but injuries limited him to 126 total games over the final three years of his contract.
Grade: C
Pittsburgh Pirates: C Russell Martin (2013)
Contract: 2 years, $17 million
The Pirates made the playoffs in both seasons that Martin served as their starting catcher, which was no small feat considering they had not reached the postseason in the 20 years prior to him joining the team. He tallied 9.8 WAR in 238 games and received down-ballot MVP votes both years before landing a five-year, $82 million deal from the Blue Jays.
Grade: A
St. Louis Cardinals: C/1B Willson Contreras (2023)
Contract: 5 years, $87.5 million
A quick reminder that Matt Holliday played 63 games for the Cardinals in 2009 after he was acquired in a midseason trade before signing his seven-year, $120 million deal, so he did not qualify for inclusion. Contreras has a terrific 127 OPS-plus in his three seasons in St. Louis, but has lost a significant chunk of his overall value since shifting from catcher to first base. Will he be traded this winter?
Grade: C
NL West
6 of 6
Arizona Diamondbacks: RHP Corbin Burnes (2025)
Contract: 6 years, $210 million
The D-backs made a surprise splash when they inked Burnes, though it was not their first dive into the deep end of the free agency pitching pool as they gave Zack Greinke a six-year, $206.5 million deal a decade earlier. He had a 2.66 ERA, 1.17 WHIP and 63 strikeouts in 64.1 innings over 11 starts before he was lost for the year to Tommy John surgery, and he is expected to open 2026 on the injured list.
Grade: Incomplete
Colorado Rockies: OF Kris Bryant (2022)
Contract: 7 years, $182 million
At 29 years old, Bryant had a NL MVP award, NL Rookie of the Year award, World Series ring and four All-Star selections on his resume, and the Rockies spent big to add him as the face of the franchise. Unfortunately, a degenerative back condition has limited him to 170 games and negative-1.6 WAR over the first four seasons of his contract, and there's a chance he has played his last game.
Grade: F
Los Angeles Dodgers: DH/RHP Shohei Ohtani (2024)
Contract: 10 years, $700 million
Two years into a contract that reshaped MLB free agency, Shohei Ohtani has won two World Series rings and two NL MVP awards while firmly establishing himself as the best player on the planet. According to insider Joon Lee, the Dodgers already made back the entirety of his $700 million contract in ticket sales, marketing deals and global merchandising in his first year with the team.
Grade: A
San Diego Padres: 3B Manny Machado (2019)
Contract: 10 years, $300 million
Machado was entering his age-26 season when he reached free agency and the Padres signed him to a massive 10-year deal, and after four seasons they inked him to a new 11-year, $350 million contract to override an impending opt-out in that initial deal. During his seven seasons in San Diego, he has three All-Star selections, three Silver Sluggers and 27.1 WAR. With 2,069 hits and 369 home runs, he is on track to surpass some major milestones before his time with the team is up.
Grade: B
San Francisco Giants: SS Willy Adames (2025)
Contract: 7 years, $182 million
A few months after signing Matt Chapman to a long-term extension, the Giants new-look front office led by Buster Posey made another splash with the Adames signing. After a slow start, he had an .828 OPS with 18 home runs after the All-Star break to reach 30 long balls for the third time in four years. Will he continue to produce into his mid-to-late 30s?
Grade: Incomplete
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