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A-Rod's laughing all the way to the bank.
The Contract: 10 years, $275 million
Stats During Contract: 620 G, .282/.370/.503, 129 HR, 447 RBI, 53 SB
In the fall of 2007, Alex Rodriguez was coming off of his second AL MVP-winning season in four years and was well on his way to becoming baseball's all-time home run king.
In a move that only seems like a good idea to people totally in love with themselves, Rodriguez and agent Scott Boras decided that Game 4 of the 2007 World Series was the appropriate time to announce that A-Rod was opting out of the 10-year, $252 million deal he was playing under.
Rodriguez would go around both Boras and Yankees GM Brian Cashman, negotiating a new contract with Hank and Hal Steinbrenner, who by this time had taken control of the franchise as their father, George, saw his health continue to deteriorate.
Now, it's true that the first three seasons of this deal were solid ones for Rodriguez and that the New York Yankees would not have won the 2009 World Series without his contributions.
But that simply doesn't make up for the dead fish that Rodriguez has become—and to whom the Yankees will be paying big money through the 2017 season.
Since signing the contract, Rodriguez has been involved with two PED scandals, admitted to doping during his days with the Texas Rangers and become one of the most reviled athletes in all of sports, not just baseball.
He's also become injury-prone, requiring surgery on both hips, the latest of which is expected to keep him out of action until after this year's All-Star break.
Rodriguez hasn't played more than 138 games in any season since signing the deal, and he's averaged only 110 games over the last two years.
His chase of Barry Bonds and Hank Aaron atop the career home run list has become essentially worthless to everyone except Rodriguez, who stands to make an extra $30 million on top of his salary if he continues to climb the charts.
The Yankees owe Rodriguez a $6 million bonus for each of five milestones that, at the time of the deal being signed, were thought to be historic milestones: tying the home run marks of Willie Mays (660), Babe Ruth (714), Hank Aaron (755) and Barry Bonds (762) and breaking Bonds' major league record.
A-Rod and his contract have become the most untradeable assets in baseball. The Yankees would take a corned beef sandwich from the Carnegie Deli in exchange for him, but there isn't a general manager alive who wouldn't think they were overpaying in that deal.