Was the Dempster Signing Smart Money?

As NBC Chicago reported earlier today, Ryan Dempster and agreed to a new four-year contract with the club. According to the Tribune's Paul Sullivan, the deal is reportedly worth $52 million. Offseason! Woo! Everyone gets money! (Ahem. Except for Kerry Wood. Sorry Kerry.)

The deal isn't exactly a bank-breaking, especially not during an offseason when C.C. Sabathia could command $140 million over six years. Even given baseball's overall salary inflation in recent seasons (which, before we start complaining, coincides with the boom in baseball revenues; players basically deserve the money), this deal isn't so bad. It's what you'd give your second-best pitcher, and that's what Ryan Dempster is to the Cubs right now. They think he's their second-best pitcher.

The problem is that he isn't quite that good, or if he is, he will have taken an unusually circuitous route in his career to get there. Dempster is 31. Next season he will be 32. This is precisely when most players begin to decline in skill. Last year, Dempster had his best season. That is unusual. Do the Cubs think he can do it twice in a row?

If so, perhaps giving him four years was worth it. Dempster will almost certainly revert back to old Dempster form -- or worse -- in 2010, but if they can get another year like 2008 out of him, chalk the remaining three up as the cost of doing business. We could see that. But if Dempster performs like Ryan Dempster has always performed, the Cubs are stuck with even more money in aging pitchers (Ted Lilly, Jason Marquis) than they'd probably like.

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