For several weeks now, we’ve been saying that Ryan Dempster’s next start could be his last as a Cub. Today it looks like he may have already made his last start for the team–and if he does take the mound this evening in St. Louis, it’s almost sure to be his last time for the Cubs. At least for this season.

The popular notion in some circles is that Dempster loves the Cubs and Chicago so much, he’ll give the team a Kerry Wood-esque discount to return next season. That theory assumes a lot, both on Dempster’s side and on the side of the Cubs’ new brain trust. Under Theo & Jed, the Cubs are getting younger, building an affordable core of young talent from within. Most people expect it to be seasons (plural) before they’re competing for the playoffs, and those are the optimistic projections (see cliches about turning around cruise ships for further details). An aging starter who–despite his recent success–has a spotty track record is most likely not on their shopping list.

On the other hand, the Cubs are very short on quality pitchers. That’s why they brought in Paul Maholm this last offseason, and why Theo & Jed will probably need to go fishing for another innings-eater next year.

If Demptster did give them a spectacular discount, it might be enough to make a return to the Northside viable. It really comes down to what other arms the Cubs are able to assemble through trades during the rest of this year and, and what is available during the offseason. I get the sense that they won’t rush a young guy to the mound just to fill a spot in the rotation. A cheap veteran would help bridge the gap between now and whenever we can field a viable, potent starting rotation.

“Cheap” being the operative word. Dempster is likely to get some excellent offers this offseason, especially if he keeps pitching like he has lately. But even if he stays on his Cy Young pace, he’s not likely to be the best pitcher available in free agency–Cole Hamels and Zack Grienke should both draw more attention and longer contracts. But those second tier guys often get good deals, too. Whether he signs ahead of the high-dollar pitchers, or he waits to sign with a team that missed on their first choice, it looks like he could cash in bigtime once more before his career is over.

But no matter what offers roll in, he’d surely have to leave most of that money on the table if he wants to return to the Cubs. I’m not saying it’s impossible–just highly unlikely. To my knowledge, it’s only happened once before, with Kerry Wood. Or twice if you count Andre Dawson’s famous blank check.

Is Dempster that kind of guy? We’ll find out in a few months.


Just a quick programming note for this weekend. On Sunday, legendary Cubs’ player and broadcaster Ron Santo will be inducted into the Hall of Fame. I’ve written before (here, here, and here) about my affection and appreciation for Santo, and I’ll be watching closely–maybe tearfully–as Ron is enshrined in Cooperstown. I’ll probably have more to say about the induction ceremony and the speeches about Ron next week.

For now I just wanted to remind you that the ceremony is at 1:30pm ET. It will be broadcast live on the MLB Network, with coverage starting around 11:30am ET. You can also see a special, updated version of This Old Cub tomorrow on the MLB Network at 1:00pm ET.

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