51 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 quicker — the tab for the richest deal in the sporting world, worth nearly a half-billion dollars, comes due in just 2.5 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, like with Stephen Strasburg and Anthony Rendon, 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: June 18, 2020

Pictured: Yogi Berra in his New York Yankees office after signing his reported $50,000 contract in 1961.

• Player information:
  • Age: 24
  • Sport: Basketball
  • Position: Center
• Contract:
  • Team: Minnesota Timberwolves
  • Value: $158,253,000
  • Years in effect: 2019-2024
  • Average per year: $31,650,600
  • Signing bonus: N/A

• Player information:
  • Age: 24
  • Sport: Basketball
  • Position: Power forward
• Contract:
  • Team: Dallas Mavericks
  • Value: $158,253,000
  • Years in effect: 2019–2024
  • Average per year: $31,650,600
  • Signing bonus: N/A

• Player information:
  • Age: 23
  • Sport: Basketball
  • Position: Shooting guard
• Contract:
  • Team: Phoenix Suns
  • Value: $158,253,000
  • Years in effect: 2019-2024
  • Average per year: $31,650,600
  • Signing bonus: N/A

• Player information:
  • Age: 33
  • Sport: Baseball
  • Position: Catcher
• Contract:
  • Team: San Francisco Giants
  • Value: $159,000,000
  • Years in effect: 2013-2021
  • Average per year: $19,875,000
  • Signing bonus: $7,000,000

• Player information:
  • Age: 35
  • Sport: Basketball
  • Position: Point guard
• Contract:
  • Team: Oklahoma City Thunder (contract signed with the Houston Rockets)
  • Value: $159,730,592
  • Years in effect: 2018-2022
  • Average per year: $39,932,648
  • Signing bonus: N/A

• Player information:
  • Age: 48
  • Sport: Baseball
  • Position: Left field
• Contract:
  • Team: Retired (contract signed with the Boston Red Sox)
  • Value: $160,000,000
  • Years in effect: 2001-2008
  • Average per year: $20,000,000
  • Signing bonus: N/A

• Player information:
  • Age: 35
  • Sport: Baseball
  • Position: Left field
• Contract:
  • Team: Miami Marlins (contract signed with the Los Angeles Dodgers)
  • Value: $160,000,000
  • Years in effect: 2012-2019
  • Average per year: $20,000,000
  • Signing bonus: $2,000,000

• Player information:
  • Age: 34
  • Sport: Baseball
  • Position: First base
• Contract:
  • Team: Baltimore Orioles
  • Value: $161,000,000
  • Years in effect: 2016-2022
  • Average per year: $23,000,000
  • Signing bonus: N/A

• Player information:
  • Age: 39
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team: Retired (contract signed with the New York Yankees)
  • Value: $161,000,000
  • Years in effect: 2009-2015
  • Average per year: $23,000,000
  • Signing bonus: N/A

• Player information:
  • Age: 30
  • Sport: Baseball
  • Position: Second base
• Contract:
  • Team: Houston Astros
  • Value: $163,500,000
  • Years in effect: 2018-2024
  • Average per year: $23,357,143
  • Signing bonus: $21,000,000

• Player information:
  • Age: 31
  • Sport: Basketball
  • Position: Small forward
• Contract:
  • Team: Brooklyn Nets (contract signed with the Golden State Warriors)
  • Value: $164,255,700
  • Years in effect: 2019-2023
  • Average per year: $41,063,925
  • Signing bonus: N/A

• Player information:
  • Age: 23
  • Sport: Basketball
  • Position: Point guard
• Contract:
  • Team: Philadelphia 76ers
  • Value: $169,650,000
  • Years in effect: 2020-2025
  • Average per year: $33,930,000
  • Signing bonus: N/A

• Player information:
  • Age: 23
  • Sport: Basketball
  • Position: Point guard
• Contract:
  • Team: Denver Nuggets
  • Value: $169,650,000
  • Years in effect: 2020-2025
  • Average per year: $33,930,000
  • Signing bonus: N/A

• Player information:
  • Age: 29
  • Sport: Basketball
  • Position: Point guard
• Contract:
  • Team: Washington Wizards
  • Value: $171,131,520
  • Years in effect: 2019-2023
  • Average per year: $42,782,880
  • Signing bonus: N/A

• Player information:
  • Age: 31
  • Sport: Basketball
  • Position: Power forward
• Contract:
  • Team: Detroit Pistons (contract signed with the Los Angeles Clippers)
  • Value: $171,174,820
  • Years in effect: 2017-2022
  • Average per year: $34,234,964
  • Signing bonus: N/A

• Player information:
  • Age: 31
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team: Washington Nationals
  • Value: $175,000,000
  • Years in effect: 2016-2023
  • Average per year: $25,000,000
  • Signing bonus: $10,000,000

• Player information:
  • Age: 34
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team: Atlanta Braves (contract signed with the Seattle Mariners)
  • Value: $175,000,000
  • Years in effect: 2013-2019
  • Average per year: $25,000,000
  • Signing bonus: $6,000,000

• Player information:
  • Age: 28
  • Sport: Basketball
  • Position: Small forward
• Contract:
  • Team: Milwaukee Bucks
  • Value: $177,500,000
  • Years in effect: 2019-2024
  • Average per year: $35,500,000
  • Signing bonus: N/A

• Player information:
  • Age: 37
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team: Houston Astros (contract signed with the Detroit Tigers)
  • Value: $180,000,000
  • Years in effect: 2013-2019
  • Average per year: $25,714,286
  • Signing bonus: N/A

• Player information:
  • Age: 27
  • Sport: Basketball
  • Position: Small forward
• Contract:
  • Team: Philadelphia 76ers
  • Value: $180,000,000
  • Years in effect: 2019-2024
  • Average per year: $36,000,000
  • Signing bonus: N/A

• Player information:
  • Age: 40
  • Sport: Baseball
  • Position: First base
• Contract:
  • Team: Retired (contract signed with the New York Yankees)
  • Value: $180,000,000
  • Years in effect: 2009-2016
  • Average per year: $22,500,000
  • Signing bonus: $5,000,000

• Player information:
  • Age: 30
  • Sport: Baseball
  • Position: Right field
• Contract:
  • Team: Chicago Cubs
  • Value: $184,000,000
  • Years in effect: 2016-2023
  • Average per year: $23,000,000
  • Signing bonus: $20,000,000

• Player information:
  • Age: 37
  • Sport: Baseball
  • Position: First base
• Contract:
  • Team: Retired (contract signed with the Minnesota Twins)
  • Value: $184,000,000
  • Years in effect: 2011-2018
  • Average per year: $23,000,000
  • Signing bonus: N/A

• Player information:
  • Age: 45
  • Sport: Baseball
  • Position: Shortstop
• Contract:
  • Team: Retired (contract signed with the New York Yankees)
  • Value: $189,000,000
  • Years in effect: 2001-2010
  • Average per year: $18,900,000
  • Signing bonus: $16,000,000

• Player information:
  • Age: 30
  • Sport: Basketball
  • Position: Shooting guard
• Contract:
  • Team: Golden State Warriors
  • Value: $189,903,600
  • Years in effect: 2019-2024
  • Average per year: $37,980,720
  • Signing bonus: N/A

• Player information:
  • Age: 29
  • Sport: Basketball
  • Position: Point guard
• Contract:
  • Team: Portland Trail Blazers
  • Value: $196,000,000
  • Years in effect: 2021-2025
  • Average per year: $49,000,000
  • Signing bonus: N/A

• Player information:
  • Age: 32
  • Sport: Basketball
  • Position: Point guard
• Contract:
  • Team: Golden State Warriors
  • Value: $201,158,790
  • Years in effect: 2017-2022
  • Average per year: $40,231,758
  • Signing bonus: N/A

• Player information:
  • Age: 36
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team: Houston Astros (contract signed with the Arizona Diamondbacks)
  • Value: $206,500,000
  • Years in effect: 2016-2021
  • Average per year: $34,416,667
  • Signing bonus: $18,000,000

• Player information:
  • Age: 31
  • Sport: Basketball
  • Position: Point guard
• Contract:
  • Team: Houston Rockets (contract signed with the Oklahoma City Thunder)
  • Value: $206,794,070
  • Years in effect: 2018-2023
  • Average per year: $41,358,814
  • Signing bonus: N/A

• Player information:
  • Age: 35
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team: Washington Nationals
  • Value: $210,000,000
  • Years in effect: 2015-2021
  • Average per year: $30,000,000
  • Signing bonus: $50,000,000

• Player information:
  • Age: 36
  • Sport: Baseball
  • Position: Designated hitter
• Contract:
  • Team: Retired (contract signed with the Detroit Tigers)
  • Value: $214,000,000
  • Years in effect: 2012-2020
  • Average per year: $23,777,778
  • Signing bonus: N/A

• Player information:
  • Age: 28
  • Sport: Baseball
  • Position: Left field
• Contract:
  • Team: Milwaukee Brewers
  • Value: $215,000,000
  • Years in effect: 2020-2028
  • Average per year: $23,888,889
  • Signing bonus: N/A

• Player information:
  • Age: 32
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team: Los Angeles Dodgers
  • Value: $215,000,000
  • Years in effect: 2014-2020
  • Average per year: $30,714,286
  • Signing bonus: $18,000,000

• Player information:
  • Age: 34
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team: Los Angeles Dodgers (contract signed with the Boston Red Sox)
  • Value: $217,000,000
  • Years in effect: 2016-2022
  • Average per year: $31,000,000
  • Signing bonus: N/A

• Player information:
  • Age: 36
  • Sport: Baseball
  • Position: First base
• Contract:
  • Team: Cincinnati Reds
  • Value: $225,000,000
  • Years in effect: 2014-2024
  • Average per year: $22,500,000
  • Signing bonus: N/A

• Player information:
  • Age: 30
  • Sport: Basketball
  • Position: Shooting guard
• Contract:
  • Team: Houston Rockets
  • Value: $228,000,000
  • Years in effect: 2017-2023
  • Average per year: $38,000,000
  • Signing bonus: N/A

• Player information:
  • Age: 40
  • Sport: Baseball
  • Position: Designated hitter
• Contract:
  • Team: Los Angeles Angels
  • Value: $240,000,000
  • Years in effect: 2012-2021
  • Average per year: $24,000,000
  • Signing bonus: N/A

• Player information:
  • Age: 37
  • Sport: Baseball
  • Position: Second base
• Contract:
  • Team: New York Mets (contract signed with the Seattle Mariners)
  • Value: $240,000,000
  • Years in effect: 2014-2023
  • Average per year: $24,000,000
  • Signing bonus: N/A

• Player information:
  • Age: 31
  • Sport: Baseball
  • Position: Starting pitcher
• Contract:
  • Team: Washington Nationals
  • Value: $245,000,000
  • Years in effect: 2020-2026
  • Average per year: $35,000,000
  • Signing bonus: N/A

• Player information:
  • Age: 30
  • Sport: Baseball
  • Position: Third base
• Contract:
  • Team: Los Angeles Angels
  • Value: $245,000,000
  • Years in effect: 2020-2026
  • Average per year: $35,000,000
  • Signing bonus: $4,000,000

• Player information:
  • Age: 37
  • Sport: Baseball 
  • Position: Designated hitter
• Contract:
  • Team: Detroit Tigers
  • Value: $248,000,000
  • Years in effect: 2016-2023
  • Average per year: $31,000,000
  • Signing bonus: N/A

• Player information:
  • Age: 44
  • Sport: Baseball
  • Position: Designated hitter
• Contract:
  • Team: Retired (contract signed with the Texas Rangers)
  • Value: $252,000,000
  • Years in effect: 2001-2010
  • Average per year: $25,200,000
  • Signing bonus: $10,000,000

• Player information:
  • Age: 29
  • Sport: Baseball
  • Position: Third base
• Contract:
  • Team: Colorado Rockies
  • Value: $260,000,000
  • Years in effect: 2019-2026
  • Average per year: $32,500,000
  • Signing bonus: N/A

• Player information:
  • Age: 44
  • Sport: Baseball
  • Position: Designated hitter
• Contract:
  • Team: Retired (contract signed with the New York Yankees)
  • Value: $275,000,000
  • Years in effect: 2008-2017
  • Average per year: $27,500,000
  • Signing bonus: $10,000,000

• Player information:
  • Age: 27
  • Sport: Baseball
  • Position: Third base
• Contract:
  • Team: San Diego Padres
  • Value: $300,000,000
  • Years in effect: 2019-2028
  • Average per year: $30,000,000
  • Signing bonus: $20,000,000

• Player information:
  • Age: 29
  • Sport: Baseball 
  • Position: Starting pitcher
• Contract:
  • Team: New York Yankees
  • Value: $324,000,000
  • Years in effect: 2020-2028
  • Average per year: $36,000,000
  • Signing bonus: N/A

• Player information:
  • Age: 30
  • Sport: Baseball
  • Position: Designated hitter
• Contract:
  • Team: New York Yankees (contract signed with the Miami Marlins)
  • Value: $325,000,000
  • Years in effect: 2015-2027
  • Average per year: $25,000,000
  • Signing bonus: N/A

• Player information:
  • Age: 27
  • Sport: Baseball
  • Position: Right field
• Contract:
  • Team: Philadelphia Phillies
  • Value: $330,000,000
  • Years in effect: 2019-2031
  • Average per year: $25,384,615
  • Signing bonus: $20,000,000

• Player information:
  • Age: 29
  • Sport: Boxing
  • Position: N/A
• Contract:
  • Streaming service: DAZN
  • Value: $365,000,000
  • Years in effect: 2018-2023
  • Average per year: $73,000,000
  • Signing bonus: N/A

• Player information:
  • Age: 28 
  • Sport: Baseball
  • Position: Center field
• Contract:
  • Team: Los Angeles Angels
  • Value: $426,500,000
  • Years in effect: 2019-2030
  • Average per year: $35,541,667
  • Signing bonus: $20,000,000

• Player information:
  • Age: 43
  • Sport: Boxing
  • Position: N/A
• Contract:
  • Streaming service: Showtime/CBS
  • Value: $450,000,000
  • Years in effect: 2013-2015
  • Average per year: $180,000,000
  • Signing bonus: N/A

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