Chicago Cubs 2016 NL Central Championship Gear

Change is in the air in Chicago, with new President of Baseball Ops Theo Epstein and presumed-new-GM Jed Hoyer on the way, ushering in an era of player development, free agency conservatism, and redirecting resources wisely away from the big-league payroll.

Here’s the thing: none of those hallmarks square particularly well with retaining 34-year-old starting pitcher, Ryan Dempster.

But the decision is not entirely up to Epstein and/or Hoyer, because Dempster holds a $14 million player option for 2012, so, if he wants to be a part of the Cubs next year, he can be. Despite the value of that option – no one is going to argue he could get more for 2012 on the open market after a few years of decline and a rough 2011 season – Dempster is still not ready to confirm he’ll be back with the Cubs next year.

“You know what’s funny is people sit there and you see the kind of money that it is and automatically you just assume that it’s a no-brainer,” Dempster said of his 2012 option. “And to me, I never played the game for money. I never do. It’s a great byproduct of what we do, but I play to go out there and try and win, and win as a team. I don’t know what the direction of the team is with somebody [new] in charge …. Do they want to go younger? Do they want to go older? Those are questions that obviously I gotta ask.

“But I love playing in Chicago. I love being a Chicago Cub, and I want to be here for the rest of my career. I’m happy that Theo is going to be in charge now and really looking forward and excited and getting an opportunity talk with him. And hopefully it’s not just picking up an option for this year, but I’ll go out there and play the best I can and be here for a long time.”

In other words, Dempster would like to remain with the Cubs in 2012 and beyond, but he’d prefer that it was on a multiyear extension, rather than a one-year option, even if that option is for great money.

The Dempster decision marks just one of many difficult spots facing the new men in charge. Dempster, who will be 35 for most of the 2012 season, is well-liked both by the fans and by his teammates. He’s been in a steady decline since the 2008 season, posting ERA+ numbers each year worse than the previous year, culminating in an 81 ERA+ this year (suggesting he was 19% worse than the average starting pitcher). Would the Cubs commit to Dempster beyond 2012?

As I see it, the Cubs have three choices when it comes to Dempster:

1.) Negotiate a two or three year extension, which reduces Dempster’s 2012 take-home to something more reasonable than $14 million, and adds a couple of years at no more than $7 to $9 million per year. That gives Dempster the security of knowing he’ll be in Chicago for the next few years (he said it isn’t about the money, though this would guarantee him more than the $14 million option), and could give the Cubs a reasonably-priced back-end starter who can simultaneously mentor the young pitchers the Cubs will hopefully soon be accumulating; or

2.) Let Dempster pick up his $14 million 2012 option, but do not extend him at this time. After 2012, depending on his health and performance, his future with the Cubs can be addressed at that time; or

3.) Gently discourage Dempster from picking up his option by informing him that the team will not be resigning him after 2012 under any circumstances. Would Dempster take the money for 2012 and leave his future uncertain? He wants to stay in Chicago, but, were he a free agent, he could probably get a two or three year deal elsewhere. This, you’ll note, is the kind of tough love Jim Hendry never had the stomach for.

Ultimately, it feels like the first is the best option. If Dempster’s annual salary is within reason, the Cubs could do a lot worse when it comes to a back-end starter over the next few years. If you take out his disastrous April (which, I know, is never a fair proposition), he had a 3.94 ERA and a .740 OPS-against this year. If he could duplicate that in 2012, he might not be worth $14 million, but he’d have a great deal of value.

As for the better of the latter two choices, number three is probably it. The Cubs are unlikely to be a top contender in 2012, and that $14 million could be put to better use, either on the amateur side, or in 2013. But, like Hendry, I’m not sure I’d have the stomach to say it, either. That’s why Epstein and Hoyer will get the big bucks.

For whatever it’s worth, Dempster sounds ready to turn things around.

“I just had a subpar year and I’m gonna go out there and bust my tail this winter. And I’m gonna … do the best I can to go out there and have a better year next year.”

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