The curse of the contract extension
Many recent examples show that early deals for superstars are ill-advised
Making matters worse, the deal didn't even start immediately; instead, it was tacked on to the end of his contract. Starting in 2012, or almost two full seasons after it was signed, Howard's new contract would run through the 2016 season, just shy of his 37th birthday.
If two seasons doesn't seem like that long, think about what Major League Baseball looked like exactly two years ago. At this time in 2012, David Wright was coming off a monster first half, and Chase Headley was in the midst of a monster stretch run; both third basemen were arguably among the top five players in the game. Over in the American League, Derek Jeter was on his way to leading the majors in hits. Justin Verlander was a year removed from being the league MVP and Cy Young winner. Nobody had ever heard of Yasiel Puig. The Houston Astros were still in the National League.
In baseball, a lot can change in a short period of time.
Of course, the Phillies obviously couldn't have anticipated that Howard would blow out his Achilles tendon in Game 5 of the 2011 NLCS. But that's sort of the point.
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A fractured foot will likely force Chris Sale to miss the Opening Day start for the White Sox.