The 10 Most Insane Sports Contracts
You won’t find a “boatload of cash” on any conversion table, but that's roughly the amount of money Giancarlo Stanton just received from the Miami Marlins.
On Wednesday, the team held a press conference to announce the outfielder’s groundbreaking 13-year, $325 million contract, per ESPN.com. That’s more than half of what it cost to build Marlins Park.
Was the investment wise or foolish? Only time will tell.
If the deal doesn’t work out, it wouldn’t be the first time a team overextended itself. Here are 10 gigantic sports contracts, ranked from mildly insane to completely bonkers. Spoiler alert—Alex Rodriguez and Rick DiPietro fall under the bonkers category.
Honorable Mentions
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Elvis Andrus, SS, Texas Rangers (8 Years, $120 Million)
Nine figures for a .272 lifetime hitter? Good one, Texas.
Clearly, the Rangers haven’t learned from their mistakes. Last offseason, they threw $130 million at Shin-Soo Choo while absorbing the remainder of Prince Fielder’s nine-year deal. The result was their worst finish since 1985.
At least Elvis Andrus and Adrian Beltre have enjoyed an interesting dynamic on the left side of the infield.
Drew Bledsoe, QB, New England Patriots (10 Years, $103 Million)
The New England Patriots thought they had a franchise quarterback in Drew Bledsoe. Then Tom Brady showed up.
Awkwarddddd.
All things considered, Bledsoe’s career didn’t turn out too badly. He got a ring as Brady’s backup in 2001 and went to the Pro Bowl a year later as a member of the Buffalo Bills.
Speaking of Buffalo, have you seen all the snow they’re getting? Mother Nature is a mad scientist, Jerry.
Carl Crawford, OF, Boston Red Sox (7 Years, $142 Million)
Remember that time Britney Spears got married in Las Vegas and had it annulled a few days later?
That pretty much describes Carl Crawford’s time in Boston. It was a mistake from the beginning, and the Red Sox realized it almost immediately. Now he’s Don Mattingly’s problem in Los Angeles.
Andy Dalton, QB, Cincinnati Bengals (6 Years, $115 Million)
Andy Dalton must have the world’s best agent. How else could you explain this preposterous contract?
Dalton still hasn’t won a playoff game, and his performance against Cleveland earlier this year was one of the worst we’ve ever seen.
The Cincinnati Bengals could back out of the deal now, and it would only cost them about $17 million, so at least it’s not a life sentence.
Ryan Howard, 1B, Philadelphia Phillies (5 Years, $125 Million)
Ryan Howard’s five-year extension began in 2012. The Philadelphia Phillies haven’t made the playoffs since 2011. You do the math.
Now the Phillies are just hoping someone will take Howard off their hands. At a rate of $25 million per season, that seems unlikely.
No. 10: Barry Zito, SP, San Francisco Giants (7 Years, $126 Million)
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Apparently, the market inefficiency in 2007 was soft-throwing left-handers.
Zito certainly milked the Giants for all he was worth, but San Francisco can’t be too upset with the outcome of his seven-year deal. After all, the team won the World Series twice during his tenure.
According to ESPN.com's Jerry Crasnick, the 36-year-old is making a comeback. If he gets signed, Zito’s next contract should be much more reasonable.
No. 9: Gilbert Arenas, G, Washington Wizards (6 Years, $111 Million)
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The Wizards inked Gilbert Arenas to a six-year deal and immediately regretted their decision. That’s called pulling a Ron Burgundy.
Arenas was never the same after gun charges forced him to miss most of the 2008-09 season. His NBA career ended after a brief stint with Memphis in 2012.
The last we heard, Arenas was gearing up for an elaborate and very illegal Fourth of July celebration. I wonder how it turned out.
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No. 8: Rashard Lewis, F, Orlando Magic (6 Years, $126 Million)
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Think Washington’s deal with Arenas was crazy? Think again.
The Orlando Magic took fiscal irresponsibility to a whole new level when they signed Rashard Lewis to a six-year contract in 2007.
Lewis averaged at least 20 points per game three years in a row before signing with the Magic. After that, he never had another 20-point-per-game season.
As fate would have it, Lewis and Arenas were traded for each other in 2010. Misery loves company.
No. 7: Vernon Wells, OF, Toronto Blue Jays (7 Years, $126 Million)
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At the time, Toronto’s decision to sign Vernon Wells to a long-term contract was ambitious. Seven years later, “ambitious” seems too kind a word.
Wells self-destructed in 2009 and was shipped out of town two years later. After two unproductive seasons in Anaheim, the Angels cut their losses and traded him to the New York Yankees. The Bronx Bombers showed him the door after one season.
Ambitious? No. Wells’ nightmare deal was nothing short of catastrophic.
No. 6: Mike Hampton, SP, Colorado Rockies (8 Years, $121 Million)
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Mike Hampton’s eight-year pact with Colorado remains one of the great heists in sports history. For Hampton, that is.
He only wound up pitching two seasons for the Rockies and was mostly a non-factor during a four-year stay in Atlanta (4.10 ERA in 509-plus innings).
To Hampton’s credit, he was an excellent hitter throughout his career (16 home runs, 79 RBI in 448 at-bats). If only he was a bit better at pitching, then he really would have been on to something.
No. 5: Johan Santana, SP, New York Mets (6 Years, $137.5 Million)
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When the New York Mets agreed to a megadeal with Santana in 2008, they thought they were signing a perennial ace. Instead, they got a lemon.
Elbow and shoulder issues limited Santana to just 109 games during his six-year stay in New York. That computes to roughly $1.26 million per start.
Suddenly, that Bobby Bonilla deal looks like a bargain.
No. 4: Ilya Kovalchuk, LW, New Jersey Devils (15 Years, $100 Million)
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The crazy thing is, this deal could have been so much worse.
Originally, the Devils and Ilya Kovalchuk agreed to a 17-year contract. Fortunately, the league intervened, and the two sides settled on a 15-year deal.
Kovalchuk never returned to the NHL after the lockout, opting to play in his native Russia. It was probably the nicest thing he could have done. By retiring, he saved the Devils $77 million.
Without this gesture of mercy, Kovalchuk would surely be in our top three.
No. 3: Albert Haynesworth, DT, Washington Redskins (7 Years, $100 Million)
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NFL Network called the Albert Haynesworth signing the “worst free-agency move of the last decade.”
That's not wrong. Haynesworth came to training camp so out of shape, he couldn’t even pass a fitness test. For a professional athlete to take such little pride in his own craft is unforgivable.
This deal certainly qualifies as a train wreck. But Washington’s ability to rid itself of Haynesworth after only two years is why it doesn’t quite take the top spot.
No. 2: Alex Rodriguez, 3B, New York Yankees (10 Years, $275 Million)
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Alex Rodriguez did win a World Series for the New York Yankees in 2009. And even though $275 million is a huge chunk of change, his contract hasn’t made the Yankees any less aggressive in free agency.
Rodriguez hasn’t crippled the Yankees financially. But it’s still bad business to give a 10 -year contract to a player in his early 30s, especially if that player has PED connections and a centaur fetish.
There’s a case to be made for A-Rod being No. 1, but we’ll spare him the embarrassment.
No. 1: Rick DiPietro, G, New York Islanders (15 Years, $67.5 Million)
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A 15-year contract with Henrik Lundqvist would be one thing, but Rick DiPietro? That’s just reckless.
Injuries limited DiPietro to 50 games over his final five seasons. Even when healthy, he only made one All-Star appearance.
Did I mention he never won a playoff series? When it comes to bad sports contracts, this one takes the cake.
Congratulations, Rick. We mean about the money—not about making this list.
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