The Most Expensive Screw-Ups in Sports History

Eric NewmanCorrespondent IIIMarch 29, 2013

The Most Expensive Screw-Ups in Sports History

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    We learn from our mistakes. Indeed! The poor sports personalities on this list learned hard and fast. And in the way it will most be remembered. That's right, the errors in this article cost folks and cost them fiercely. In some cases to the sorrowful tune of hundreds of millions.

    So dot those i's and cross those t's.

    Double-check the blueprints. Double-check those deadlines. 

    Click on too sea sum of the expensivest sports goofs of awl time. 

20. Tannenbaum's Sanchez Extension

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    Former Jets general manager Mike Tannenbaum gambled that an unproven Sanchez would be the Jets' golden boy.

    He signed Sanchez to a long-term contract extension. The Jets wound up 6-10 for the 2012 season. Sanchez gave up 18 interceptions and eight fumbles (the same exact numbers he put up for the 2011 season).

    Coupled with the Tebow fiasco, the Jets are in a hot mess QB-wise.

    And as for Tannenbaum? He's currently seeking employment.

19. Keith Mcleod's Missing Date

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    In the fall of 2011, the Spartans were making a run for the Scottish Cup. The team defeated Culter 2-0. However, a new contract that Spartan striker Keith Mcleod had signed the summer before was only dated once (rules dictate contracts must be dated twice). Crime of the century?

    Apparently it was; Mcleod was deemed to have been ineligible to play.

    The Spartan's were fined and thrown out of the tournament, losing out on a possible lucrative payout.

18. 1952 Topps Cards: The Burial at Sea

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    Got a glut of product? Dump it in the Atlantic. That's what the top brass over at Topps decided to do with their leftover '52s. (Think Mickey Mantle, think Willie Mays, think Jackie Robinson, think Pee Wee Reese.)

    Uh, fellas, wouldn't the wiser choice have been to warehouse the packs and sell them later for millions and millions?

    Ok, 20/20 hindsight, I know. But breaks your heart, doesn't it?

17. Cliff Avril Loses Out on the Lion's Share

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    A team offers you $30 million for 3 years of service; they must really want your services, right? Which means other teams would probably want them too.

    Those magic words start ringing in your ears: BIDDING WAR!

    So you turn down the 30 and wait for the big payout of...


    Whoopsie daisy.

16. Sultan Mizan Zainal Abidin Stadium Roof Collapses...Twice

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    What will close to $100 million buy you in the way of a stadium? Well, partner up that price tag with "serious engineering flaws, shoddy workmanship, inferior materials and lack of expertise in the key project management team" and you win...

    A roof that collapses after one year.

    And then again a few years after that. 

15. Raptors Field for Nash Flop

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    The soap opera summary:

    The Raptors want Steve Nash. The Knicks do, too. 

    The Raptors try to stymie the Knicks by offering big money to the underperforming Landry Field, who is the NY Knicks' only viable bargaining chip at this point. 

    Nash winds up with the Lakers. 

    The Raptors are still licking their wounds.

14. John Elway: Ponzied

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    Captain Comeback steered his finances into troubled waters when he and a business partner sank $15 million into a hedge fund managed by one Sean Mueller. 

    Mueller apparently got his hedging credentials with UPS. No, not the shipping company— it's the University of Ponzi Schemes I'm referring to. You know that school where Bernie Madoff graduated valedictorian?

    Mueller was arrested. 

    At least $3 million of Elway's investment are MIA.

13. Elvis Dumervil: Fax Gate

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    The offseason was looking spot-on for the Broncos. They scored big-time by snatching up Wes Welker. And again when they got Elvis Dumervil to stick around—with a pay cut!

    Only Dumervil's agent sent back the signed contract seven minutes past the NFL deadline. Dumervil became a free agent and then a Raven.

12. Ronaldinho's $1,550,000 Million Can of Pepsi

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    If you have a sponsorship deal with Nike, keep those Adidas hidden away in the back of your closet. If you have a sponsorship deal with Burger King, eat your Big Macs on the sly. 

    But the most obvious of all... If you are on the Coca-Cola payroll, keep your Pepsi in a brown paper bag.

    Woe to Ronaldinho, once proud sponsor of Coca-Cola who allegedly refreshed his palette with a sip of the wrong sweet nectar while speaking at a press conference for his new team, Atletico Mineiro.

    Coke canceled the contract, which still had more than a million-and-a-half US dollars in unpaid earnings. 

11. Rick DiPietro Gets 15 Years

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    Here's a stat for you: About fifty percent of NHL goalies last three seasons or less. Goaltending is notoriously tough on the knees, you see.

    So it must have taken a great mind to sign Rick DiPietro to a 15-year, $67.5 million deal with the New York Islanders. 

    And what do you know, just after signing, DiPietro's knees went all kablooey on him. So he spends much of his time on the bench figuring out what to do with the next yearly installment of $4.5 million.

10. Chelsea's Winston Bogarde Botch-Up

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    Ever hear the story of how Erik the Red named an desolate icy landmass Greenland so as to attract settlers? Some say it was the best marketing ploy in history.

    Well, Dutch soccer player Mario Melchiot may have trumped it. Somehow, he got Chelsea to take on the very mediocre Winston Bogarde for a very non-mediocre salary worth about £10 million over 4 years.

    Bogarde and the bench became good friends. 

9. 38 Studios: Game Over

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    As part of an economic development program, the state of Rhode Island offered former MLB pitcher Curt Schilling's fledgling video game company $75 million in loans. Money that came from the taxes of the good citizens of the state.

    Schilling, a man who reportedly lacked any business experience, took the carrot.

    The company put out one game then tanked.

    Schilling lost $50 million of his own fortune. Rhode Island is out the $75 million plus millions more in interest.

8. Buying Your Kid Hockey Gear

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    To equip your future Sidney Crosby hopefuls, this is about what you'll shell out.

    • Helmet: $50-$80
    • Pads: $150-$200
    • Skates: $60-$100
    • Stick: $20-$100
    • Miscellaneous items (hockey bag, stick tape, blade guards, etc.): $50
    • Total: $330-$530

    Three years later, when your kid gives up hockey and asks for improv classes instead, you'll be lucky to sell it all at a yard sale for $20.

7. Joao Havelange Stadium Roof Design

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    The majestic Rio de Janeiro stadium is just six years old; it was built for the 2007 Panamerican Games. Currently, it is Botafogo Football Club's home. It's next big international duty is to host the athletics events at the 2016 Olympic games.

    That is, if it doesn't pancake first. 

    Rio mayor Eduardo Paes has ordered the stadium closed indefinitely as a result of flawed construction that could lead to a roof collapse. 

    The stadium may need a multi-million dollar redux, if that is even possible and feasible. If not, Rio will have to churn out a new venue fast and furious-like. 

6. Gene Chizik's Contract Extension

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    Gene Chizik had a couple of good years with Auburn. Under his leadership, the Tigers had a 14-0 season and nabbed their first national title in more than 50 years.

    Chizik was someone Auburn athletic director Jay Jacobs wanted to keep around. So Jacobs offered a very, very lucrative contract extension.

    The next year, the Tigers lost their claws, finishing with a woeful 3-9.

    Chizik was the man of the hour no more. So he was paid $7.5 stop coaching.

5. Olympics Triplecast Belly Flops

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    NBC, who had the rights to the 1992 Summer Games in Barcelona, gambled that viewers would open up their wallets to see events live rather than with a tape delay. From that notion the Olympics Triplecast was born.

    Three pay-per-view channels: red, white, and blue, each featuring different live events.

    Very few people subscribed. Those that did weren't happy with what they got.

    The Triplecast will forever be the Ford Edsel of broadcast projects. The New Coke of soft drinks. The Hindenburg of airships.

4. Charles Pic’s $30 Million Dollar Braking Error

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    Fact: At the end of the Formula 1 season, the 10th place team gets a $40 million slice of media rights income.

    Fact: The 11th place team gets about a $10 million slice.

    So Charles Pic’s little braking error at the third turn of the 65th lap of the 2012 season-ending Brazilian Grand Prix cost the Marussia F1 Team oh so dearly.

3. The USFL Debacle

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    Launched in 1983, the United States Football League was a rival to the NFL. But not really. It bled, then hemorrhaged, then bled out. The league folded in 1985. 

    And it's no wonder with the ridiculous contract deals it made. Like the one given to QB Steve Young. Forty-three years, $40 million. Go ahead, read that again.

2. Lance Armstrong Fesses Up

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    Is it a screw-up to tell the truth? Certainly not. Coming clean is almost always the right thing to do. But maybe when the whole world already knows the truth anyway and gazillions of dollars of personal income are at stake...

    Well, silence has its merits.

1. Tiger Woods' 120 Alleged Infidelities

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    Some reports have Tiger clocking in at about 120 mistresses. With his loss of sponsorship deals and his divorce settlement, one estimate of his losses totals about $132.2 million. Or put another way, just over a million dollars per tryst.