Why Chicago Cubs Should Beat the Rush at MLB Trade Deadline and Buy Now

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The Cubs are in the middle of a good season. While the Brewers are seemingly entrenched in first place, Chicago has a chance to secure home-field advantage in their inevitable best-of-3, as the Wild Card leader. But the schedule is about to flip.

The Cubs are about to play games in 17 straight days, then one off day, then play another nine in a row. Teams they'll face in this stretch are designed to feast on weaker pitching: the Dodgers, Nationals, Yankees, and White Sox stand out as tough opponents. It’s not an exaggeration to say that this segment will dictate their October plans.

This article isn’t going to talk about targets. Northside has that covered here and here (shout out to Sam Caulder, he’s been outstanding), and if you prefer to listen, it’s talked about right here. This is about the timing.

Playing 26 in 27 days will stretch and tax any rotation, but the Cubs aren’t just any rotation. They are already using retreads like Aaron Civale and claiming DFA'd relievers left and right, hoping to find this year’s Drew Pomeranz. They clearly feel the urgency and the need.

So, make a trade. Today. Put away the IVY model machine, forget the future value nitpicking, and try to keep this ship afloat.

With 26 IL stints on the club this year from pitchers alone, this long stretch of games requires reinforcements on the hill. The Cubs have Matt Shaw, who has a lot of future value. Is it in Chicago? Probably, he’ll have more value somewhere else that doesn’t have their entire infield under contract, blocking him, for years. He’s a perfect example of a player the model values highly, but who won’t achieve that value unless moved to greener pastures.

So whatever it is—controllable starter, high-leverage rental reliever—just do the trade now. Stop trying to extract maximum theoretical value in every move. Jed Hoyer has built an elite defensive team with a solid offense. He needs to cash in some chips to address the pitching staff. The next month will sorely test the Cubs;. Will they get reinforcements? They can’t risk another 30-game, 7-23 stretch. That could derail an interesting season. They need to gear up for the grind right this minute.

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Brian Kelder is a lifelong Cub fan, and given the increasing length of his life is becoming a very long time. Along with this great site, you can find his writing at Razzball and Bulls Confidential. Other than that, he's probably drinking coffee or walking in the woods.