Shohei Ohtani is widely expected to sign a record breaking contract this offseason. The following list shows the biggest free agent contract of each MLB offseason dating back to Mark Langston in 1990.
Contracts signed by Barry Bonds ahead of the 1993 season, Albert Belle in 1997, Kevin Brown in 1999, Alex Rodriguez in 2001, Max Scherzer in 2015 and Aaron Judge in 2023 represent inflection points in what is possible contractually for MLB free agents.
The current era of the MLB has seen fewer superstars actually become free agents by signing extensions such as Mike Trout’s 12-year, $426.5 million deal with the Angels in 2019.
* When the average annual value was similar, the larger overall contract was counted as the biggest one from the year.
- 1990: Mark Langston, Angels, $16 million, five years ($3.2 million AAV)
- 1991: Darryl Strawberry, Dodgers, $20.25 million, five years ($4.1 million AAV)
- 1992: Bobby Bonilla, Mets, $29 million, five years ($5.8 million AAV)
- 1993: Barry Bonds, Giants, $43.75 million, six years ($7.3 million AAV)
- 1994: Will Clark, Rangers, $30 million, five years ($6 million AAV)
- 1995: Larry Walker, Rockies, $22.5 million, four years ($5.6 million AAV)
- 1996: David Cone, Yankees, $19.5 million, three years ($6.5 million AAV)
- 1997: Albert Belle, White Sox, $55 million, five years ($11 million AAV)
- 1998: Kenny Lofton, Indians, $24 million, three years ($8 million AAV)
- 1999: Kevin Brown, Dodgers, $105 million, seven years ($15 million AAV)
- 2000: Greg Vaughn, Rays, $34 million, four years ($8.5 million AAV)
- 2001: Alex Rodriguez, Rangers, $252 million, 10 years ($25.2 million AAV)
- 2002: Jason Giambi, Yankees, $120 million, seven years ($17.1 million AAV)
- 2003: Jim Thome, Phillies, $87.5 million, six years ($14.6 million AAV)
- 2004: Vladimir Guerrero, Angels, $70 million, five years ($14 million AAV)
- 2005: Carlos Beltran, Mets, $119 million, seven years ($17 million AAV)
- 2006: Johnny Damon, Yankees, $52 million, four years ($13 million AAV)
- 2007: Alfonso Soriano, Cubs, $136 million, eight years ($17 million AAV)
- 2008: Alex Rodriguez, Yankees, $275 million, 10 years ($27.5 million AAV)
- 2009: Mark Teixeira, Yankees, $180 million, eight years ($22.5 million AAV)
- 2010: Matt Holliday, Cardinals, $120 million, seven years ($17.1 million AAV)
- 2011: Cliff Lee, Phillies, $120 million, five years ($24 million AAV)
- 2012: Albert Pujols, Angels, $254 million, 10 years ($25.4 million AAV)
- 2013: Josh Hamilton, Angels, $125 million, five years ($25 million AAV)
- 2014: Robinson Cano, $240 million, 10 years ($24 million AAV)
- 2015: Max Scherzer, $210 million, seven years ($30 million AAV)
- 2016: Zack Greinke, $206.5 million, six years ($34.4 million AAV)
- 2017: Yoenis Cespedes, $110 million, four years ($27.5 million AAV)
- 2018: Yu Darvish, Cubs: $126 million, six years ($21 million AAV)
- 2019: Bryce Harper, Phillies, $330 million, 13 years ($25.4 million AAV)
- 2020: Gerrit Cole, Yankees, $324 million, nine years ($36 million AAV)
- 2021: Trevor Bauer, Dodgers, $102 million, three years ($34 million AAV)
- 2022: Corey Seager, Rangers, $325 million, 10 years ($32.5 million AAV)
- 2023: Aaron Judge, Yankees, $360 million, nine years ($40 million AAV)
- 2024: Shohei Ohtani, ???, $??? million, ? years