Top 50 Sports Contracts For 2019

42. Todd Helton – Colorado Rockies, Major League Baseball:

Helton signed a nine-year contract in April 2001 and then a two-year extension with Colorado in March 2010. His deal totaled 11 years and $151,500,000, with an average of $13,772,727 per season and $85,016.83 per game.

Helton played all 17 of his seasons with Colorado and holds the club records for hits (2,519), home runs (369), doubles (592), walks (1,335), runs scored (1,401), runs batted in (RBI, with 1,406), games played (2,247), and total bases (4,292). He was definitely worth every penny of his contract.

41. Miguel Cabrera – Detroit Tigers, Major League Baseball:

Former MVP and Triple Crown Winner Cabrera signed an eight-year, $152,300,000 extension with Detroit in March 2008. The contract averaged $19,037,500 per season and $117,515.43 per game. At the time, it was the fourth-largest agreement in baseball history.

Cabrera won the Triple Crown in 2012 and the American League’s Most Valuable Player Award from 2012-2013. He has been hindered by injury the past two years, yet his track record proves his massive signing was by far a worthy one for the Tigers.          

40. Mike Conley – Memphis Grizzlies, Basketball:

Conley signed a five-year deal with the Memphis Grizzlies worth $152,605,576 in 2016. The deal averages $30,521,115 a season and $372,208.72 per game.

He averaged a career-high mark in per-game scoring average and became Memphis’ all-time scoring leader during 2018-2019, proving the contract was a good decision.

38. (tie). Kimi Räikkönen – Ferrari, Auto Racing:

Räikkönen left McLaren to sign a three-year deal with Scuderia Ferrari following the 2006 Italian Grand Prix. The huge deal paid him $153,000,000 with an average of $51,000,000 per year and $2,942,307.69 per race.

Ferrari announced he would be leaving their company towards the end of the 2009 season in exchange for driver Fernando Alonso. The deal may not have been quite as big of a home run the racing giant had hoped for.

38 (tie). Jacoby Ellsbury – New York Yankees, Major League Baseball:

Ellsbury signed a seven-year, $153,000,000 contract with the infamous New York Yankees in 2013. The deal averages $21,857,142 a season and $134,920.64 a game, with an option for an eighth season that extends the full value to $169 million.

The massive deal hasn’t exactly proven to be a great signing, as Ellsbury has dealt with many injuries over the past three seasons from 2017-2019.

37. Adrián González – Boston Red Sox, Major League Baseball:

González was traded to the Boston Red Sox for four players in 2010. He then signed a seven-year, $154,000,000 contract before the 2011 year that averaged $22,000,000 a year and $135,802.67 per game.

He was traded to the Dodgers in August 2012, suggesting it was not the greatest deal.

35 (tie). Masahiro Tanaka – New York Yankees, Major League Baseball:

Japanese hurler Tanaka signed a seven-year, $155,000,000 contract with the Yankees in 2014 after his team Rakuten posted him to MLB and made a cool$20 million fee. His deal averaged $22,141,857 a year and $136,684.30 a game.

He opted not to utilize the opt-out clause for the last three years of his contract in late 2017. Tanaka is still throwing heat for the Yankees. This was a solid deal.

35 (tie). Jon Lester – Chicago Cubs, Major League Baseball:

The Cubs lavished a six-year, $155,000,000 deal on Lester in late 2015. It averaged $25,833,333 a year and $159,465.02 per game.

He pitched in relief duty in their Game 7 in the 2016 World Series where they beat Cleveland in historic fashion to break their World Series drought. He threw as the Cubs’ Opening Day starter for the third consecutive season in 2019, suggesting this was another solid deal.

34. Troy Tulowitzki – Colorado Rockies, Major League Baseball:

The now-34-year-old Tulowitzki signed a ludicrous 10-year, $157,750,000 deal averaging $15,775,000 per year and $97,376.54     per game in late 2010.

The unreal shortstop had torn up the National League for several years. But he unfortunately ran into injuries. He hurt his groin, rib, and hip in successive seasons. The onetime star was traded to the Toronto Bluejays in 2015. He then hurt his quad, hamstring, and ankle in a second three-year stretch. He now earns the league minimum for the New York Yankees. This did not end up being a good deal.

32 (tie). Matt Kemp – Los Angeles Dodgers, Major League Baseball:

Slugger Kemp signed a Los Angeles-record eight-year, $160,000,000 deal with the team following 2011. It paid him an average of $20,000,000 per season and $123,456.79 per game.

Kemp was traded to the San Diego Padres in 2014, then to the Atlanta Braves, Dodgers again, and the Reds. Cincinnati released him on May 4. The New York Mets signed him to a minor league deal three weeks later. This record deal did not pan out for LA.

32 (tie). Manny Ramírez – Boston Red Sox, Major League Baseball:

Ramirez signed an eight-year, $160,000,000 contract that actually ended up being 10 years and $200 million with Boston in December 2000. The deal had options for two final years averaged $20,000,000 a year and $123,456.79 a game.

He was looking for a straight-up 10-year contract from the start. But it didn’t matter. Ramirez became a Red Sox legend. Over his career, he hit .312 batting average, 555 home runs, and 1,831 RBI while helping Boston finally win the World Series. Great deal.

30 (tie). CC Sabathia – New York Yankees, Major League Baseball:

Sabathia signed a seven-year, $161,000,000 averaging $23,000,000 a year and $141,975.31 a game in December 2008. The contract was then a record for the biggest pitcher deal in baseball history.

It paid off immediately as New York won the World Series in 2009. Sabathia is a six-time All-Star. He experienced some injuries in the middle of his run with the Yanks but has gotten back on track the past three seasons. A huge deal that was worth it.

30 (tie). Chris Davis – Baltimore Orioles, Major League Baseball:

Davis signed a seven-year, $161,000,000 contract with the Baltimore Orioles in early 2016 after hitting 47 home runs and 117 runs batted in (RBI) in 2015. The massive signing averaged $23,000,000 a year and $141,975.31 a game.

He proceeded to hit .221 the first year of the deal with a league-leading 219 strikeouts. Davis followed that up with a .215 batting average and 195 strikeouts the following season.

But he hit some new lows in 2018 with a. 168 batting average, .243 on base percentage, and .296 slugging percentage. All of those figures were the lowest in the league. This was not a good deal, but somehow he still plays for Baltimore.

29. Buster Posey – San Francisco Giants, Major League Baseball:

All-Star Posey signed a nine-year $167,000,000 deal with the San Francisco Giants in 2013. The massive contract averaged $18,555,556 a year and $114,540.47 per game.

Posey has hit .304 with 1,314 hits, 135 home runs, and 652 RBI For San Francisco, winning two World Series titles also. This was a good deal.

28. Blake Griffin – Los Angeles Clippers, Basketball:

Griffin signed with the Los Angeles Clippers for 5 years and $172,260,000 in July 2017. The contract averaged $34,452,000 a season and $420,146.34 a game.

This was not a strong contract. Griffin was largely injured after he signed it and later traded to the Detroit Pistons.

26 (tie). Félix Hernández – Seattle Mariners, Major League Baseball:

Hernandez signed with the Mariners for 7 years and $175,000,000 in February 2013, voiding the last years of his previous deal. The contract averaged $25,000,000 a season and $154,320.99 a game.

“King Felix” broke the record for the biggest pitching contract in baseball history. Justin Verlander broke it one month later. It’s debatable as to how good this deal is after time has passed. He was one of the more dominant pitchers in baseball for quite a while, yet injuries have plagued him for the past few years.

26 (tie). Stephen Strasburg – Washington Nationals, Major League Baseball:

Strasburg extended his contract with the Nats for 7 years and $175,000,000 in 2016. The contract extension averaged a staggering $25,000,000 a year and $154,320.99 a game.

He’s racked up a 101-56 record with 1,559 strikeouts for Washington, and despite some serious injuries, he’s pitched well.

24 (tie). Mark Teixeira – New York Yankees, Major League Baseball:

Following a slugging start to his career with Texas, the Braves, and the Angels, Teixeira signed on for 8 years and $180,000,000 with New York in 2008. The deal averaged $22,500,000 a season, $138,888.89 per game, and included a $5 million signing bonus.

Teixeira won the World Series with the Yanks in 2009. He also hit 39 home runs and 111 RBI in 2011. But he unfortunately went through a long series of injuries from there on out. They sapped him of his skills and he retired in 2016. This deal wasn’t what it could have been.

24 (tie). Justin Verlander  – Detroit Tigers, Major League Baseball:

Verlander re0signed with the Tigers, the team that drafted him in 2005, He re-signed with the team for 7 years and $180,000,000 before the 2013 season. His contract was the biggest in MLB history for a pitcher at the time. It averaged $25,714,286 per season and $158,730.16 per game.

Verlander was worth it even though he had a pair of mediocre years in 2012 and 2013. Following his big 2011 season, he was the second pitcher in history to win all three of the Rookie of the Year, Cy Young, and Most Valuable Player awards. He was the Cy Young runner-up in 2016. The Tigers traded him to the Houston Astros for three players at the trade deadline in 2017. He was the American League Championship (ALCS) MVP and promptly helped the Astros win the World Series that year. Whatever he got paid, he earned it.

22 (tie). Joe Mauer – Minnesota Twins, Major League Baseball:

Mauer signed with Minnesota for 8 years and $184,000,000 in 2010. It made him the highest-paid catcher in baseball history and averaged $23,000,000 per season and $141,975.31 a game.

Mauer was the first American League catcher to win a batting title, and he did it three times. He deserved to make what he did in that deal. The Twins great retired in 2018.

22 (tie). Jason Heyward – Chicago Cubs, Major League Baseball:

Outfielder Heyward signed an eight-year, $184,000,000 deal with the Cubs in late 2015. The deal averaged $23,000,000  a season and $141,975.31 a game.

Heyward had a letdown first season in Chicago. But he paid for it in spades by leading an inspirational meeting during a World Series rain delay. He also became the first position player in MLB history to win three consecutive Gold Gloves for three different teams that season. This contract was solid because it helped the Cubbies finally win the World Series.

21. Derek Jeter – New York Yankees, Major League Baseball:

Jeter signed with the Yankees for 10 years and $189,000,000 after they drafted him in the 1992 draft and he played for six successful years. The deal averaged $18,900,000 a year and $116,666.67 each game.

It’s beyond safe to say the deal was worth it. Jeter played his entire 20-year career with the Yankees, batting .310 with 3,465 hits, 260 home runs, and 1,311 RBIs. He’s also the Yankees’ all-time leader in hits, games played, stolen bases, plate appearances, and at-bats. He also hit .321 in the World Series.

20. Stephen Curry – Golden State Warriors, Basketball:

Curry re-signed with Golden state for 5 years and $201,200,000 before the 2017 season. The massive NBA deal averaged $40,200,000 a season and $490,243.90 a game.

Curry has won two NBA MVP awards and three titles with the Warriors. It could be argued that he almost singlehandedly changed the game of professional basketball with its renewed focus on three-point shots. You could argue Curry is the best shooter in NBA history. He set the NBA record for threes in 2013 and broke it in 2015 and 2016. He’s earned every dollar of his huge payday.

19. Russell Westbrook – Oklahoma City Thunder, Basketball:

Westbrook re-signed with the Oklahoma Thunder for 5 years and $205,000,000 in September 2017. The massive deal is the biggest guaranteed contract in NBA history and contains an option for a sixth year, making it $233 million total. It averages $41,000,000 per year and $491,000.00 per game.

The Thunder haven’t won the title with Westbrook, but it isn’t his fault. He averaged a triple-double for three straight seasons. He’s arguably the most complete player in the NBA today and would earn this kind of money on essentially any team.

18. Zack Greinke – Arizona Diamondbacks, Major League Baseball:

This is remarkably the second appearance Greinke makes on this list. He signed a six-year, $206,500,000 with Arizona in December 2015. The deal pays him $34,416,667 per year and $212,448.56 per game.

Greinke has earned his many massive paydays. He’s made the All-Star team the last two seasons and has won four straight Golden Gloves. His exhaustive preparation for each start is often respected, proving that he works hard to make his huge paydays.

17. Max Scherzer – Washington Nationals, Major League Baseball:

Scherzer signed a strange seven-year contract with the Washington Nationals in January 2015 that paid him $210,000,000    total. It pays him $30,000,000 a season and $185,185.19 a game and also includes a $50 million signing bonus over 14 years.

Scherzer threw two no-hitters in 2015 and won his second and third Cy Young awards in 2016 and 2017, respectively. This was a good deal.

16. Prince Fielder – Detroit Tigers, Major League Baseball:

In January 2012, former Milwaukee star Fielder signed with Detroit for 9 years and $214,000,000. At the time, it was the largest contract in the history of the team when it topped surpassing Miguel Cabrera’s 8-year, $185.3 million deal. It paid Fielder an average of $23,777,777 a season and $146,776.40 per game.

He was later traded to the Texas Rangers in November 2013. He retired in 2016 after sustaining serious neck injuries. It’s tough to call his contract a bad deal because injuries sapped him of his skills, but clearly, it didn’t work out for the Tigers.

15. Clayton Kershaw – Los Angeles Dodgers, Major League Baseball:

Ace Kershaw re-signed with LA for a record 7 years and $215,000,000 after the 2013 season. The contract pays him $30,714,285 a season, a record for highest single-season value in baseball, and $186,120.37 a game.

The deal once again set the record for biggest contract MLB for a pitcher. Kershaw has earned every dime, however. He won his third Cy Young and the National League MVP award the year after he signed the contract, and led the Dodgers to the World Series in 2017.

14. David Price – Boston Red Sox, Major League Baseball:

Price signed with the Red Sox for 7 years and $217,000,000 in late 2015. It was a Boston record. The contract topped Kershaw’s aforementioned record for single-season value at $31,000,000 and averaged $191,358.02 per game.

He went through several nagging injuries during the 2017 season but bounced back strong in 2018. There, Price started the Red Sox’ World Series-clinching Game 5, earning the American League Comeback Player of the Year award. It’s safe to say this huge deal was a good one.

13. Joey Votto – Cincinnati Reds, Major League Baseball:

Votto re-signed with the Reds for 10 years and $225,000,000 in April 2012. The deal also included the last two years on his prior contract, making his new contract 12 years and $251.5 million. It was the longest contract in MLB at the time. It paid him $22,500,000 a season and $138,888.89 a game.

Votto has played his entire career with the Reds since 2007. He has hit .309 with 1,797 hits, 277 home runs, and 917 RBI. While he plays in a smaller market of Cincinnati, he’s the face of the franchise. He’s also been as consistent as they come. This was a good signing.

12. James Harden – Houston Rockets, Basketball:

The bearded star re-signed with the Rockets for 4 years and $160,000,000 in the summer of 2017. The extension was added to the 4-year, $118.1 million deal he was given the previous summer. All told, his contract was six years and $228 million guaranteed, the biggest contract in NBA history. It pays him $38,000,000 per year and $463,414.64 per game.

Harden was named the league MVP following the 2017-2018 NBAA year. The Rockets haven’t won a title with him as their top player, but he is essentially the team. His streak of 30-point games last season was unbelievable. It could be argued he’s the most effective scorer in the NBA, so this was a deal that had to be paid.

10 (tie). Robinson Canó – Seattle Mariners, Major League Baseball:

Cano signed a massive 10-year, $240,000,000 with Seattle in December 2013. The deal was for a cool $24,000,000 a season and $148,148.15 per game.

Cano made the All-Star game in three out of the following four seasons, winning the game’s MVP award in 2017. He was suspended for using diuretics the following season. Cano was traded to the New York Mets in late 2018.

10 (tie). Albert Pujols – Los Angeles Angels, Major League Baseball:

The Angels signed Pujols away from the St. Louis Cardinals for 10 years and$ 240,000,000 in late 2011. The massive deal averaged $24,000,000 a season and $148,148.15 a game.

It’s hard to say it was fully worth it, however. Pujols has seen his batting average dip consistently after signing with Los Angeles, including career-lows of career-lows in batting average, on base percentage, slugging, doubles, and walks in 2017. He tied his career-low for RBI with 64 in 2018.

9. Miguel Cabrera – Detroit Tigers, Major League Baseball:

Like Greinke, Cabrera makes a second appearance on the list when he re-signed with Detroit 8 years and $247,000,000 before the 2016 season. The extension averaged $31,000,000 a year and $191,358.02 per game.

Like it was mentioned earlier, he has been plagued by injuries in recent years, so it’s tough to say if this deal will be worth it.

8. Alex Rodriguez – Texas Rangers, Major League Baseball:

Rodriguez signed with Texas for 10 years $252,000,000 before the 2001 season in his first appearance of two on the list of richest sports contracts. At the time, it was the biggest contract in MLB history by a large margin. It outpaced every other MLB contract by $63 million in fact. The deal averaged $25,200,000 a season and $155,555.56 per game.

It wasn’t worth it for the Texas Rangers. Rodriguez was gone from the team by 2003, heading to sign another huge long-term deal with the Yankees.

7. Nolan Arenado – Colorado Rockies, Major League Baseball:

This deal rates as one of the newer huge deals on the list. Arenado signed with the Rockies for 8 years and $260,000,000 before the 2019 season. The contract extension averages $32,500,000 a year and $200,617.28 a game.

The jury is still out on this particular contract extension as the player is still in the first year of it.

6. Alex Rodriguez – New York Yankees, Major League Baseball:

‘A-Rod’s’ second appearance on this list with his controversial contract with the Yankees. Initially, he and agent Scott Boras said he would not re-sign with New York because he “was unsure of the future composition” of the team. However, relief pitcher Mariano Rivera convinced A-Rod to stay. He signed for 10 years and $275,000,000, averaging $27,500,000 a season and $169,753.09 a game. The deal was laden with incentives based on home run-hitting milestones.

Rodriguez was later involved in the Biogenesis of America performance-enhancing drug scandal in 2009. In January 2014, he admitted to the EA he had used PEDs. He was suspended for the entire 2014 season as a result. The league suspended Rodriguez for the “use and possession of numerous forms of prohibited performance-enhancing substances, including Testosterone and human Growth Hormone (hGH), over the course of multiple years” and “attempting to cover-up his violations of the Program by engaging in a course of conduct intended to obstruct and frustrate the Office of the Commissioner’s investigation.” It’s hard to say his contract was worth it based on that.

5. Manny Machado – San Diego Padres, Major League Baseball:

Former Oriole and Los Angeles Dodger Machado signed for 10 years and $300,000,000 with San Diego before this year began. The contract pays him $30,000,000 per year and $185,185.19 per game. It was the biggest free-agent contract in baseball history until another name on this list signed a bigger deal two weeks later.

Like Nolan Arenado earlier on this list, the jury is still out on if the deal was worth it.

4. Giancarlo Stanton – Miami Marlins, Major League Baseball:

The Marlins thought it wise to sign Stanton to a 13-years, $325,000,000 million deal in November 2014, the largest total contract in team sports history at the time. It averaged $25,000,000 a season and $154,320.99 a game.

He hit .281 with 59 home runs and 132 RBI in 2017, winning the MVP award for the National League. But the Marlins traded him to New York after the season, making him only the second player in Major League history to be traded after a 50-home run year. It’s fair to wonder why Miami lavished such a long, expensive contract on Stanton only to trade him after he had his best statistical output of all-time.

3. Bryce Harper – Philadelphia Phillies, Major League Baseball:

Harper signed with the Phillies for 13 years and $330,000,000 in 2019. The contract was the biggest in the history of baseball and North American team sports at the time. The deal pays Harper $25,384,615 a season and $156,695.16 per game.

As is the case with two of the huge new deals of Manny Machado and Nolan Arenado, we’re not sure just how worth it this record deal is just yet. But Harper is a six-time All-Star and was the 2015 NL MVP. The Phillies were ready to spend big money, so there wasn’t a more high-profile name to pick up outside of Harper.

2. Canelo Álvarez – Boxing (DAZN):

Star boxer Álvarez signed with streaming service DAZN for 5 years and 11 fights for a total of $365,000,000 in November 2018. The deal averages $73,000,000 a year and $33,181,818.18 per fight. The deal would replace his previous contract with HBO.

With Álvarez one of the biggest stars in boxing, this deal is worth it even if it absolutely huge. DAZN made big waves in the sports world with the signing.

1. Mike Trout – Los Angeles Angels, Major League Baseball:

Finally, we’ve reached the richest overall sports contract on our list. Superstar Trout re-signed with the Angels for 12 years and $426,500,000 in March 2019. The signing topped Bryce Harper’s deal as the biggest in the history of baseball and North American team sports. The extension pays Trout $35,541,666 a year and $219,393 a game.

Largely touted as the No. 1 player in baseball, the Angels had no other move to make here. Trout is a two-time American League MVP. He rewarded the Angels for signing him to such a huge extension by becoming the AL Player of the Week for the fourth time this April.