MLB Free Agency 2012: Grading Matt Cain and 10 Biggest Player Extensions

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MLB Free Agency 2012: Grading Matt Cain and 10 Biggest Player Extensions
Ezra Shaw/Getty Images

There have been quite a few baseball players who have signed contract extensions with their respective teams in the past couple of months. Some of them will turn out to be solid investments for the team, and others will keep owners and general managers up all night in regret.

Handing out extensions is risky business.

Sure, it sends a heartwarming message to the player that the club truly values them and that they don't want to risk losing him via free agency. However, it's very difficult to gauge what the market value will be for a specific player unless they actually hit the open market, so there always runs the risk of overpaying.

But that is where the hometown discount comes into play, which organizations undoubtedly desire every one of their players to take when signing an extension.

Players like Jered Weaver, who signed a five-year, $85 million contract last year, is the epitome of a player willing to take a hometown discount. Weaver could've made upwards of $120 million if he wished to test the free-agent market when the time came.

So while some players elected to take a discount, others held out for what the potential market value could've been had they became a free agent.

With that in mind, here's a grade for the 10 biggest contract extensions that were handed out recently.

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