Originally written on Midwest Sports Fans  |  Last updated 10/23/14
Before Wednesday’s game against the Detroit Tigers, Cubs president The Epstein and pitcher Ryan Dempster were seen having a long conversation. The two say they were discussing a fundraiser that Dempster has. That could be true, but with all the trade speculation surrounding Dempster, anyone who is naive enough to think that was not part of the conversation is foolish. Ryan Dempster and Theo Epstein chatted recently … about what, nobody knows. (Image credit: Phil Velasquez via the Chicago Tribune) Dempster’s Value At Its Peak The Cubs know they are in full sell-off-assets mode, and even the most optimistic fans of the optimistic fan base realize that. Aside from maybe Starlin Castro and Jeff Samardzija, anyone on the ball club with any sort of value should be prepared to pack their bags. Ryan Dempster, with his 2.31 ERA, makes for the Cubs’ best trade chip, and his current success is exactly why the Cubs should not wait to deal him. While he’s pitching like one of the best pitchers in the game right now, he is a career .500 pitcher (right around there, at 114-119) and is 35 years old. Really, how realistic is it to expect anything other than a decline, maybe even a steep one, from the guy at some point this season? That’s exactly why Epstein and company should not wait to make a deal involving Ryan Dempster: his asking price is never going to be higher than it is right now. The Cubs may want more than what other teams are offering, but again, the offers are not going to get any better. Even if it’s not what they want, it’s time to do something now before some sort of decline settles in. In my opinion, the Cubs need more pitching than hitting when it comes to prospects, and of all the trade partners out there, the one that matches up the best with that is the Detroit Tigers. Detroit has a few good young arms that are looking to break through into an MLB rotation within the next year or so (Jacob Turner and Casey Crosby to name a few), and a veteran, rotation-ready second or third starter is a desperate need of theirs at this point. So, Theo, it’s time to get on the phone, give Detroit or someone else a call, and start working the magic that all Cubs fans are expecting. You and Jed Hoyer called the MLB Draft your “Super Bowl.” Well, if that’s the big game, this next month and a half might be your NFC Championship.

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