65 Biggest Sports Contracts Ever

In the late 1950s, New York Yankees catcher Yogi Berra paid the bills by working in the offseason as a waiter. This was not uncommon. Shortly after shutting out the Los Angeles Dodgers in Game 2 of the 1966 World Series, Baltimore Orioles pitcher Jim Palmer supplemented his income to the tune of $150 a week selling suits at a men’s clothing store. NFL legend Jim Brown held a side gig as a sales rep with Pepsi, Hall of Fame quarterback Y.A. Tittle sold insurance and Dodgers outfielder Carl Furillo ran a deli.

Today’s top players don’t have to worry about working a side gig in the offseason. Nine-figure contracts, once unheard of, are now the norm for the biggest sports stars. Some of the largest contracts are spread out over a dozen years or more. Other athletes collect much more quickly, raking in untold riches in a little more than two years. 

In this study, GOBankingRates aggregated noteworthy contracts across multiple sports and ranked the most lucrative ones in descending order, from lowest to highest. The study used data from Spotrac, MLB and ESPN to dig into the contracts further. Boxing, baseball and basketball contracts came out on top. In some cases, more than one player tied with the same contract value, so readers should expect to see some values repeated. 

Keep reading to find out which players inked the deals that made them the highest-paid athletes in history.

Last updated: July 12, 2021

• Player information:
  • Sport: Basketball
  • Position: Point guard
• Contract:
  • Team at time of signing: Denver Nuggets
  • Current team/status (if different): N/A
  • Value: $158,253,000
  • Length of contract: 5 years (2020-2024)
  • Average per year: $31,650,600
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Basketball
  • Position: Small forward
• Contract:
  • Team at time of signing: New Orleans Pelicans
  • Current team/status (if different): N/A
  • Value: $158,253,000
  • Length of contract: 5 years (2020-2024)
  • Average per year: $31,650,600
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Basketball
  • Position: Power forward
• Contract:
  • Team at time of signing: Dallas Mavericks
  • Current team/status (if different): N/A
  • Value: $158,253,000
  • Length of contract: 5 years (2019–2024)
  • Average per year: $31,650,600
  • Signing bonus: N/A
  • End of Contract: Current

• Player information:
  • Sport: Basketball
  • Position: Center
• Contract:
  • Team at time of signing: Minnesota Timberwolves
  • Current team/status (if different): N/A
  • Value: $158,253,000
  • Length of Contract: 5 years (2019-2024)
  • Average per year: $31,650,600
  • Signing bonus: N/A
  • End of Contract: Current

Explore: Pro Athletes Who Have Lost Millions of Dollars

• Player information:
  • Sport: Basketball
  • Position: Shooting guard
• Contract:
  • Team at time of signing: Phoenix Suns
  • Current team/status (if different): N/A
  • Value: $158,253,000
  • Length of Contract: 5 years (2019-2024)
  • Average per year: $31,650,600
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Catcher
• Contract:
  • Team at time of signing: San Francisco Giants
  • Current team/status (if different): N/A
  • Value: $159,000,000
  • Length of contract: 8 years (2013-2021)
  • Average per year: $19,875,000
  • Signing bonus: $7,000,000
  • End of contract: Current

• Player information:
  • Sport: Basketball
  • Position: Point guard
• Contract:
  • Team at time of signing: Houston Rockets
  • Current team/status (if different): Phoenix Suns
  • Value: $159,730,592
  • Length of contract: 4 years (2018-2022)
  • Average per year: $39,932,648
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Left field
• Contract:
  • Team at time of signing: Los Angeles Dodgers
  • Current team/status (if different): Miami Marlins
  • Value: $160,000,000
  • Length of contract: 2012-2019
  • Average per year: $20,000,000
  • Signing bonus: $2,000,000
  • End of contract: Released

• Player information:
  • Sport: Baseball
  • Position: Left field
• Contract:
  • Team at time of signing: Boston Red Sox
  • Current team/status (if different): Retired
  • Value: $160,000,000
  • Length of contract: 8 years (2001-2008)
  • Average per year: $20,000,000
  • Signing bonus: N/A
  • End of contract: Retired

• Player information:
  • Sport: Football
  • Position: Quarterback
• Contract:
  • Team at time of signing: Dallas Cowboys
  • Current team/status (if different): N/A
  • Value: $160,000,000
  • Length of contract: 4 years (2021 – 2024)
  • Average per year: $40,000,000
  • Signing bonus: $10 million
  • End of contract: Upcoming

• Player information:
  • Sport: Baseball
  • Position: First base
• Contract:
  • Team at time of signing: Baltimore Orioles
  • Current team/status (if different): N/A
  • Value: $161,000,000
  • Length of contract: 7 years (2016-2022)
  • Average per year: $23,000,000
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team at time of signing: New York Yankees
  • Current team/status (if different): Retired
  • Value: $161,000,000
  • Length of contract: 7 years (2009-2015)
  • Average per year: $23,000,000
  • Signing bonus: N/A
  • End of contract: Retired

• Player information:
  • Sport: Basketball
  • Position: Power forward
• Contract:
  • Team at time of signing: Boston Celtics
  • Current team/status (if different): N/A
  • Value: $163,000,590
  • Length of contract: 5 years (2021-2025)
  • Average per year: $32,600,118
  • Signing bonus: N/A
  • End of contract: Upcoming

• Player information:
  • Sport: Basketball
  • Position: Power forward
• Contract:
  • Team at time of signing: Miami Heat
  • Current team/status (if different): N/A
  • Value: $163,000,590
  • Length of contract: 5 years (2021-2025)
  • Average per year: $32,600,118
  • Signing bonus: N/A
  • End of contract: Upcoming

• Player information:
  • Sport: Basketball
  • Position: Shooting guard
• Contract:
  • Team at time of signing: Utah Jazz
  • Current team/status (if different): N/A
  • Value: $163,000,590
  • Length of contract: 5 years (2021-2025)
  • Average per year: $32,600,118
  • Signing bonus: N/A
  • End of contract: Upcoming

• Player information:
  • Sport: Basketball
  • Position: Point guard
• Contract:
  • Team at time of signing: Sacramento Kings
  • Current team/status (if different): N/A
  • Value: $163,000,590
  • Length of contract: 5 years (2021-2025)
  • Average per year: $32,600,118
  • Signing bonus: N/A
  • End of contract: Upcoming

• Player information:
  • Sport: Baseball
  • Position: Second base
• Contract:
  • Team at time of signing: Houston Astros
  • Current team/status (if different): N/A
  • Value: $163,500,000
  • Length of contract: 7 years (2018-2024)
  • Average per year: $23,357,143
  • Signing bonus: $21,000,000
  • End of contract: Current

• Player information
  • Sport: Basketball
  • Position: Small forward
• Contract:
  • Team at time of signing: Golden State Warriors
  • Current team/status (if different): Brooklyn Nets
  • Value: $164,255,700
  • Length of contract: 2019-2023
  • Average per year: $41,063,925
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Basketball
  • Position: Point guard
• Contract:
  • Team at time of signing: Denver Nuggets
  • Current team/status (if different): N/A
  • Value: $169,650,000
  • Length of contract: 5 years (2020–2025)
  • Average per year: $33,930,000
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Basketball
  • Position: Point guard
• Contract:
  • Team at time of signing: Washington Wizards
  • Value: $171,131,520
  • Years in effect: 4 years (2019-2023)
  • Average per year: $42,782,880
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Basketball
  • Position: Power forward
• Contract:
  • Team at time of signing: Los Angeles Clippers
  • Current team/status (if different): Detroit Pistons
  • Value: $171,174,820
  • Length of contract: 5 years (2017-2022)
  • Average per year: $34,234,964
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team at time of signing: Washington Nationals
  • Current team/status (if different): N/A
  • Value: $175,000,000
  • Length of contract: 7 years (2016-2023)
  • Average per year: $25,000,000
  • Signing bonus: $10,000,000
  • End of contract: Opted out

• Player information:
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team at time of signing: Seattle Mariners
  • Current team/status (if different): Atlanta Braves
  • Value: $175,000,000
  • Length of contract: 7 years (2013-2019)
  • Average per year: $25,000,000
  • Signing bonus: $6,000,000
  • End of contract: Expired, not revisited

• Player information:
  • Sport: Basketball
  • Position: Point guard
• Contract:
  • Team at time of signing: Philadelphia 76ers
  • Current team/status (if different): N/A
  • Value: $169,650,000
  • Length of contract: 5 years (2020-2025)
  • Average per year: $33,930,000
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Basketball
  • Position: Small forward
• Contract:
  • Team at time of signing: Milwaukee Bucks
  • Current team/status (if different): N/A
  • Value: $177,500,000
  • Length of contract: 5 years (2019-2024)
  • Average per year: $35,500,000
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: First base
• Contract:
  • Team at time of signing: New York Yankees
  • Current team/status (if different): Retired
  • Value: $180,000,000
  • Length of contract: 8 years (2009-2016)
  • Average per year: $22,500,000
  • Signing bonus: $5,000,000
  • End of contract: Expired/retired

• Player information:
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team at time of signing: contract signed with the Detroit Tigers
  • Current team/status (if different): Houston Astros
  • Value: $180,000,000
  • Length of contract: 7 years (2013-2019)
  • Average per year: $25,714,286
  • Signing bonus: N/A
  • End of contract: Expired, followed by extension

• Player information:
  • Sport: Basketball
  • Position: Small forward
• Contract:
  • Team at time of signing: Philadelphia 76ers
  • Current team/status (if different): N/A
  • Value: $180,000,000
  • Length of contract: 5 years (2019-2024)
  • Average per year: $36,000,000
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: First base
• Contract:
  • Team at time of signing: Minnesota Twins
  • Current team/status (if different): Retired
  • Value: $184,000,000
  • Length of contract: 2011-2018
  • Average per year: $23,000,000
  • Signing bonus: N/A
  • End of contract: Expired

• Player information:
  • Sport: Baseball
  • Position: Right field
• Contract:
  • Team at time of signing: Chicago Cubs
  • Current team/status (if different): N/A
  • Value: $184,000,000
  • Length of contract: 8 years (2016-2023)
  • Average per year: $23,000,000
  • Signing bonus: $20,000,000
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Left field
• Contract:
  • Team at time of signing: Milwaukee Brewers
  • Current team/status (if different): N/A
  • Value: $215,000,000
  • Length of contract: 7 years (2020-2028)
  • Average per year: $23,888,889
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Shortstop
• Contract:
  • Team at time of signing: New York Yankees
  • Current team/status (if different): Retired
  • Value: $189,000,000
  • Length of contract: 2001-2010
  • Average per year: $18,900,000
  • Signing bonus: $16,000,000
  • End of contract: Expired, followed by extension

• Player information:
  • Sport: Basketball
  • Position: Power forward
• Contract:
  • Team at time of signing: Los Angeles Lakers
  • Current team/status (if different): N/A
  • Value: $189,903,600
  • Length of contract: 5 years (2020-2024)
  • Average per year: $37,980,720
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Basketball
  • Position: Shooting guard
• Contract:
  • Team at time of signing: Golden State Warriors
  • Current team/status (if different): N/A
  • Value: $189,903,600
  • Length of contract: 5 years (2019-2024)
  • Average per year: $37,980,720
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Basketball
  • Position: Point guard
• Contract:
  • Team at time of signing: Portland Trail Blazers
  • Current team/status (if different): N/A
  • Value: $196,000,000
  • Length of contract: 4 years (2021-2025)
  • Average per year: $49,000,000
  • Signing bonus: N/A
  • End of contract: Upcoming

• Player information
  • Sport: Basketball
  • Position: Point guard
• Contract:
  • Team at time of signing: Golden State Warriors
  • Current team/status (if different): N/A
  • Value: $201,158,790
  • Length of contract: 4 years (2017-2022)
  • Average per year: $40,231,758
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Basketball
  • Position: Center
• Contract:
  • Team at time of signing: Utah Jazz
  • Current team/status (if different): N/A
  • Value: $205,000,002
  • Length of contract: 5 years (2021-2025)
  • Average per year: $41,000,000
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team at time of signing: Arizona Diamondbacks
  • Current team/status (if different): Houston Astros
  • Value: $206,500,000
  • Length of contract: 6 years (2016-2021)
  • Average per year: $34,416,667
  • Signing bonus: $18,000,000
  • End of contract: Current

• Player information:
  • Sport: Basketball
  • Position: Point guard
• Contract:
  • Team at time of signing: Oklahoma City Thunder
  • Current team/status (if different): Houston Rockets
  • Value: $206,794,070
  • Length of contract: 5 years (2018-2023)
  • Average per year: $41,358,814
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team at time of signing: Washington Nationals
  • Current team/status (if different): N/A
  • Value: $210,000,000
  • Length of contract: 7 years (2015-2021)
  • Average per year: $30,000,000
  • Signing bonus: $50,000,000
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Designated hitter
• Contract:
  • Team at time of signing: Detroit Tigers
  • Current team/status (if different): Retired
  • Value: $214,000,000
  • Length of contract: 9 years (2012-2020)
  • Average per year: $23,777,778
  • Signing bonus: N/A
  • End of contract: Released/retired

• Player information:
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team at time of signing: Los Angeles Dodgers
  • Current team/status (if different): N/A
  • Value: $215,000,000
  • Length of contract: 7 years (2014-2020)
  • Average per year: $30,714,286
  • Signing bonus: $18,000,000
  • End of contract: Opted out

• Player information:
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team at time of signing: Boston Red Sox
  • Current team/status (if different): Los Angeles Dodgers
  • Value: $217,000,000
  • Length of contract: 7 years (2016-2022)
  • Average per year: $31,000,000
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: First base
• Contract:
  • Team at time of signing: Cincinnati Reds
  • Current team/status (if different): N/A
  • Value: $225,000,000
  • Length of contract: 10 years (2014-2024)
  • Average per year: $22,500,000
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Basketball
  • Position: Shooting guard
• Contract:
  • Team at time of signing: Houston Rockets
  • Current team/status (if different): N/A
  • Value: $228,000,000
  • Length of contract: 6 years (2017-2023)
  • Average per year: $38,000,000
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Basketball
  • Position: Power forward 
• Contract:
  • Team at time of signing: Milwaukee Bucs
  • Current team/status (if different): N/A
  • Value: $228,200,826
  • Length of contract: 5 years (2021-2025)
  • Average per year: $45,640,165
  • Signing bonus: N/A 
  • End of contract: Upcoming

• Player information:
  • Sport: Baseball
  • Position: Second base
• Contract:
  • Team at time of signing: Seattle Mariners
  • Current team/status (if different): New York Mets
  • Value: $240,000,000
  • Length of contract: 10 years (2014-2023)
  • Average per year: $24,000,000
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Designated hitter
• Contract:
  • Team at time of signing: Los Angeles Angels
  • Current team/status (if different): N/A
  • Value: $240,000,000
  • Length of contract: 10 years (2012-2021)
  • Average per year: $24,000,000
  • Signing bonus: N/A
  • End of contract: Released, signed smaller contract with Dodgers

• Player information:
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team at time of signing: Washington Nationals
  • Current team/status (if different): N/A
  • Value: $245,000,000
  • Length of contract: 7 years (2020-2026)
  • Average per year: $35,000,000
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Third base
• Contract:
  • Team at time of signing: Los Angeles Angels
  • Current team/status (if different): N/A
  • Value: $245,000,000
  • Length of contract: 7 years (2020-2026)
  • Average per year: $35,000,000
  • Signing bonus: $4,000,000
  • End of contract: Current

• Player information:
  • Sport: Baseball 
  • Position: Designated hitter
• Contract:
  • Team at time of signing: Detroit Tigers
  • Current team/status (if different): N/A
  • Value: $248,000,000
  • Length of contract: 8 years (2016-2023)
  • Average per year: $31,000,000
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Designated hitter
• Contract:
  • Team at time of signing: Texas Rangers
  • Current team/status (if different): Retired
  • Value: $252,000,000
  • Length of contract: 2001-2010
  • Average per year: $25,200,000
  • Signing bonus: $10,000,000
  • End of contract: Opted out

• Player information:
  • Sport: Baseball
  • Position: Third base
• Contract:
  • Team at time of signing: Colorado Rockies
  • Current team/status (if different): St. Louis Cardinals
  • Value: $260,000,000
  • Length of contract: 8 years (2019-2026)
  • Average per year: $32,500,000
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Designated hitter
• Contract:
  • Team at time of signing: New York Yankees
  • Current team/status (if different): Retired
  • Value: $275,000,000
  • Years in effect: 10 years (2008-2017)
  • Average per year: $27,500,000
  • Signing bonus: $10,000,000
  • End of contract: Released/retired

• Player information:
  • Sport: Baseball
  • Position: Third base
• Contract:
  • Team at time of signing: San Diego Padres
  • Current team/status (if different): N/A
  • Value: $300,000,000
  • Length of contract: 10 years (2019-2028)
  • Average per year: $30,000,000
  • Signing bonus: $20,000,000
  • End of contract: Current

• Player information:
  • Sport: Baseball 
  • Position: Starting pitcher
• Contract:
  • Team at time of signing: New York Yankees
  • Current team/status (if different): N/A
  • Value: $324,000,000
  • Length of contract: 9 years (2020-2028)
  • Average per year: $36,000,000
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Designated hitter
• Contract:
  • Team at time of signing: Miami Marlins
  • Current team/status (if different): New York Yankees
  • Value: $325,000,000
  • Length of contract: 13 years (2015-2027)
  • Average per year: $25,000,000
  • Signing bonus: N/A

• Player information
  • Sport: Baseball
  • Position: Right field
• Contract:
  • Team at time of signing: Philadelphia Phillies
  • Current team/status (if different): N/A
  • Value: $330,000,000
  • Length of contract: 13 years (2019-2031)
  • Average per year: $25,384,615
  • Signing bonus: $20,000,000
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Short stop
• Contract:
  • Team at time of signing: San Diego
  • Current team/status (if different): N/A
  • Value: $340,000,000
  • Length of contract: 14 years (2021-2034)
  • Average per year: $24,285,714
  • Signing bonus: $10,000,000
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Short stop
• Contract:
  • Team at time of signing: New York Mets
  • Current team/status (if different): N/A
  • Value: $341,000,000
  • Length of contract: 10 years (2021-2031)
  • Average per year: $34,100,000
  • Signing bonus: $21,000,000
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Right field
• Contract:
  • Team at time of signing: Los Angeles Dodgers
  • Current team/status (if different): N/A
  • Value: $365,000,000
  • Length of contract: 12 years (2020-2032)
  • Average per year: $30,416,667
  • Signing bonus: $65,000,000
  • End of contract: Current

• Player information:
  • Sport: Boxing
  • Position: N/A
• Contract:
  • Streaming service: DAZN
  • Value: $365,000,000
  • Years in effect: 5 years (2018-2023)
  • Average per year: $73,000,000
  • Signing bonus: N/A
  • End of contract: Current

• Player information:
  • Sport: Baseball
  • Position: Center field
• Contract:
  • Team at time of signing: Los Angeles Angels
  • Current team/status (if different): N/A
  • Value: $426,500,000
  • Length of contract: 12 years (2019-2030)
  • Average per year: $35,541,667
  • Signing bonus: $20,000,000
  • End of contract: Current

• Player information:
  • Sport: Football
  • Position: Quarterback
• Contract:
  • Team at time of signing: Kansas City Chiefs
  • Current team/status (if different): N/A
  • Value: $450,000,000
  • Length of contract: 10 years (2020-2031)
  • Average per year: $45,000,000
  • Signing bonus: $10,000,000
  • End of contract: Current

• Player information:
  • Sport: Boxing
  • Position: N/A
• Contract:
  • Streaming service: Showtime/CBS
  • Value: $450,000,000
  • Length of contract: 2.5 years (2013-2015)
  • Average per year: $180,000,000
  • Signing bonus: N/A
  • End of contract: Retired with scattered fights, runs own production company

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Andrew Lisa contributed to the reporting for this article. 

Photo disclaimer: Please note that photos are for representation purposes only and may not reflect the athlete’s current team.