Do the Indians Have a Shot at Signing Jake Westbrook?

When the Indians traded Jake Westbrook to the Cardinals this summer, there was a near-universal suggestion that the Tribe could sign him this off-season, since 2010 was the final year of his three-year contract extension.

Now that he’s played a few months with the Cardinals, the notion that we have a shot to bring Jake back into the fold is looking to be less than a sure thing.

According to Derrick Goold of the St. Louis Post Dispatch, Jake is already thinking about a potential deal with the Cardinals:

“I’m definitely going to be open-minded about pretty much everything.  If [the Cardinals] had interest, I’ve definitely enjoyed my time here. I’ve gotten to know the guys well. The organization is definitely one that everybody knows about, that I’ve certainly heard a lot about, and now, firsthand, I’ve gotten to see that everybody was right.”

There’s not a lot to that quote in my opinion: it sounds like pretty benign player-speak to me.  My suspicion is that Jake, like all baseball players, is going to want to get his first taste of free agency before signing with anyone.

But it still begs the point: was trading Jake worth the increased likelihood that we cost ourselves a chance to sign him back?  Is it even true that moving Jake makes it less likely for the Indians to sign him?

These questions come up a lot, and teams like the Indians have to weigh the benefits of trading players like Jake (cutting payroll and getting prospects) with the cost of potentially not keeping the player around for upcoming seasons.

In fact, I’m reminded of the Carl Pavano move last year.  Pavano’s underlying performance with the Tribe was actually pretty good in 2009, and anyone who was looking closely knew that he was likely to have a better 2010.  But once he got a taste of a contending club, it was unlikely that he’d sign back with a rebuilding team like the Indians.  Sure enough, he signed a deal with the Twins over the winter and will likely be their number two starter in the playoffs.

Trading Westbrook and Pavano were, in my opinion, the right moves to make.  But I have to remind myself of the possibility that moving these guys in the last months of their deals does make it more difficult to sign them.  A taste of winning and contention will do that to a player.

When Jake hits free agency, I would give the Indians nearly no chance to sign him: not only will we likely low-ball him on a contract compared to other offers, but we’re also not in a great position to make the playoffs next year—something the Cardinals (and other teams) can likely offer.  Maybe we’re better off going young next year, but I can’t help but wonder if trading Jake cost us any chance we had to have him here in 2011.