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The 9 biggest, and 3 weirdest sports contracts of all time

The big, the bold, and mustache addendums!

World Series - Boston Red Sox v Los Angeles Dodgers - Game Five Photo by Harry How/Getty Images

The Padres and free agent Manny Machado are finalizing terms on a 10-year, $300M contract, which would be the richest in free agent history. The move will likely change the landscape of future baseball contracts, and could bleed into other sports when up-and-coming stars are due to get their payday.

This got us thinking: What are the largest sports contracts in history, what were their terms, and is there a bigger contract we all might have forgotten?

The three largest free agent contracts in history.

No. 1 — Manny Machado, 10-years, $300M, San Diego Padres (2018)

World Series - Boston Red Sox v Los Angeles Dodgers - Game Four Photo by Harry How/Getty Images

Machado was the crown jewel in MLB free agency this year with the Yankees, Phillies, White Sox, Angels, Cubs, and Dodgers all being finalists for the 26-year-old’s services. Assuming Machado plays every game for the duration of the contract it will net him a cool $185,185 per game.

No.2 — Alex Rodriguez, 10-years, $275M, New York Yankees (2008)

A-Rod wins the award for contract hustle. He managed to negotiate his deal with the Yankees, under tenuous terms (after opting out of his final year), all without his superstar agent Scott Boras.

No. 3 (tied) — Robinson Cano, 10-years, $240M, Seattle Mariners (2014)
Albert Pujols, 10-years, $240M, Los Angeles Angels (2012)

Cano spurned the Yankees in a move that was shocking at the time. Reportedly offered a seven-year, $175M deal, Cano wanted a longer-term deal that would presumably carry him through the end of his career (he was 31 when the deal as signed). In the end it was Seattle who ponied up to the table and made it happen.

Pujols was a career Cardinal when he was reportedly insulted by the team when they offered to only give him a five-year contract extension. Teams lined up for his services, but ultimately went with the Angels after they agreed to add a no-trade clause to the contract.

The three largest contract extensions of all time.

No.1 — Giancarlo Stanton, 13-years, $325M, Miami Marlins (2014)

While this isn’t the biggest contract in terms of yearly salary or per-game, it is the highest total extension an athlete has reached. That long-term deal looks brilliant now for Stanton, who was traded to the Yankees, while the Marlins are still the Marlins.

No.2 — Miguel Cabrera, 8-years, $247M, Detroit Tigers (2014)

Hot off the heels of his second MVP season, Cabrera cashed in to the tune of $247M. He’s made three all-star appearances in that time.

No.3 — James Harden, 6-years, $226M, Houston Rockets (2017)

Houston Rockets v Phoenix Suns Photo by Christian Petersen/Getty Images

Harden’s supermax extension paid him like an entire team — because, well, he kind of is an entire team if you think about it.

The three largest sports contracts of all time, per game/appearance

No. 1 — Canelo Álvarez, $33M per fight, DAZN

This one is simply mind-boggling. In 2018 Álvarez inked a five-year deal with the streaming service DAZN to exclusively carry his next 11 fights. That was signed for a total of $365M, meaning that every time he gets in the ring he’s earning over $30M, before he gets to share gate tickets, marketing dollars, etc.

Simply astounding.

No.2 — Kimi Räikkönen, $2.9M per race, Ferrari

Formula 1 will never crack the top list when it comes to total contract size, but considering the short term of contracts it’s here where F1 shines. Räikkönen signed a three-year, $153M deal in 2007 that paid him over $50M a year, and almost $3M a race.

No. 3 — Michael Shumacher, $1.9M per race, Ferrari

Michael Schumacher of Germany and the Ferrari team celebrates with team principal Jean Todt

Shumacher signed a four-year, $124M deal with Ferrari, which may have been less than Räikkönen overall — but it should be noted it was inked in 1996. No contract during the mid nineties touched what Shumacher was earning. Nothing.

The three weirdest contract clauses of all time.

No. 1 — Rollie Fingers’ mustache addendum, Oakland Athletics (1973)

I had you at “mustache addendum,” didn’t I? This rider, built into Fingers’ 1973 contract extension came after Fingers won an in-club mustache competition. It declared that for the duration of Fingers’ one-year-deal he would be supplied with “the finest mustache wax money could buy.”

No. 2 — Stefan Schwartz must stay on Earth (2002)

Soccer player Stefan Schwartz was well-known for his love of outer space, and Sunderland knew this. So concerned was the English Premier League team in 2002 that they added an addendum into his contract saying he “must remain on Earth,” as a means to protect their investment.

Schwartz did not go to space.

No. 3 — Roy Oswalt gets a bulldozer (2005)

Cincinnati Reds v Houston Astros Photo by Bob Levey/Getty Images

Oswalt’s dream was to own a bulldozer, so in 2005 Drayton McLane drew up an agreement that said if Oswalt won Game 6 of the NCLS he would get a bulldozer. He did, and the rest is history.