What the Hell Were You Thinking? Jake Westbrook Edition

*Over the next couple of weeks, Jorge Says No! will take an in depth look at some of the worst contracts in baseball. We'll evaluate why the player was signed, what went wrong, and future implications of the contract. Behind every bone head decision, there has to be a reason for it...right?*

Before the 2007 season began, the Indians signed Jake Westbrook to a contract extension from 2008-2010. During that time period, Westbrook has made just 5 starts for the Indians as the team has plummeted in the standings and has been forced to deal away two of their star pitchers. So what the hell were you thinking, Cleveland?

Why Re-Sign Westbrook: Even though Westbrook was far from an ace, he was a consistent and steady presence in the Indians' rotation and could be counted on to give the team 200+ IP every season. The 2007 free agent class was horrifically weak with starting pitchers, which is important because Westbrook would have been highly sought after on the open market. Realistically, the Indians probably knew that their chances of resigning CC Sabathia after the 2008 season were slim to none and it was important for the team to lock up a member of their starting rotation. Furthermore, the Indians were impressed with Westbrook's leadership abilities and thought very highly of him.

As GM Mark Shapiro noted at the time:

"Given the market for quality starting pitching, it's reasonable to assume that a healthy Westbrook could command somewhere in the neighborhood of $10 million a year. Rather than approach Westbrook about an extension at the end of the season, before the market got out of whack, the Tribe picked up his '07 option worth $6.1 million.

"Jake is a guy we value and believe in," Shapiro said. "He's truly taken on a leadership role as well. He's a guy we'd like to have here beyond next year."

What Went Wrong: Westbrook made 25 starts in 2007 after signing the extension, but he went down early in 2008 with elbow pain. Initially, Westbrook thought that he would be able to pitch through the pain, but by June, Westbrook was forced to undergo Tommy John Surgery that knocked him out for the rest of the 2008 season and all of the 2009 season.

Future Implications: Westbrook's extension is set to expire after this year so the impact of the contract will probably be minimal from here on out, but make no mistake about it, this deal has hinder the Indians' financial flexibility. In 2008, the Indians were forced to trade free agent to be CC Sabathia because they could not afford to resign him. In 2009, the Indians decided to move Cliff Lee even though he was signed through 2010 because they were convinced that they could not sign him. Westbrook's annual salary ($11 million) takes up roughly 14% of the Indians total payroll, which is a crushing blow for GM Mark Shapiro over the past year and a half.

Lesson Learned: I dunno if there is a specific lesson that the Indians can take from the Westbrook extension because injuries have forced Westbrook to miss most of the last two seasons. The Indians took a gamble by signing Westbrook to a long term extension, but the results have not been pretty. At the same time, if a small market team is going to spend 1/7th of their total payroll on a pitcher, his ceiling should be higher than that of a middle of the rotation starting pitcher, don't cha think?


Thoughts?

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