Dempster Diving: Predicting Where Ryan Dempster Will Sign

Ryan Dempster

Ryan Dempster may be one of the most interesting free agent pitchers of 2012. Despite pitching 200+ innings and having an ERA under 4.00 in four of the past five years, Dempster will likely be at best the Plan B option for teams who miss out on the prime free agent pitching talent this off season.

So why won’t he get more love?

First, Dempster will turn 36 next season. Secondly, after his mid-season trade to the Rangers, Dempster got absolutely lit up. There haven’t been that many hit balls in Texas since Debbie Does Dallas was released.

But because of his track record, durability and versatility (Dempster has closed games in the past) he should find a team willing to pay him millions for a one to two-year deal. Let’s look at where he might end up:

1. Milwaukee Brewers – The Brewers have expressed interest in bringing Zack Greinke back, but he might be too pricey. Dempster could be a good fallback option. He knows the NL Central from his days with the Cubs and the Brew Crew’s lineup would give Dempster plenty of run support for a change. But at this stage of his career, I think Dempster is chasing a ring more than money. Is Milwaukee good enough to entice him?

2. Toronto Blue Jays The Jays have traded for or signed just about every other free agent this year, so why not Dempster too? Toronto GM Alex Anthopoulos said in October he was going to revamp his pitching staff. And with the trade for Josh Johnson and Mark Buerhle … he’s obviously serious. Signing Dempster would give them a rotation nearly as strong as Tampa’s which is a must in the AL East. But with all their new acquisitions, will they have enough cash to make Dempster a good offer?

3. Detroit Tigers This suggestion deserves an asterisk. If Anibal Sanchez signs a big free agent contract elsewhere, I think Detroit would be interested in Dempster to fill out their rotation behind Verlander. It would put Dempster on a team that is going to win a lot of games and be a near lock for the playoffs in the horrible Al Central. Plus, the bratwursts in Michigan are almost as good as Dempster’s beloved Chicago.

And finally the team I believe Dempster will sign with:

4. The New York Yankees – This makes too much sense. The Yankees are in desperate need to shore up their rotation and can’t keep relying on studs from their past like Pettitte and Clemens to magically appear and bail them out (rumor is Ron Guidry and Whitey Ford both turned Brian Cashman down already.) And we all know money is no object to the evil pinstripe empire. I’m thinking Dempster signs with New York on a 1 year – $10 Million type deal

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Patrick O'Connor
Patrick O'Connor is an award-winning screenwriter currently focusing on feature comedies. He previously was a staff writer on the hit Disney animated show Kick Buttowski: Suburban Daredevil. He spent 11 years as a news writer/producer at KTLA-TV  where he won two Emmy awards, four Golden Mikes and two AP Writing awards. Follow him on Twitter @thepatoconnor