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Come Fan with UsSaturday, June 20, 2026

The Storm Clouds Over The Cubs’ Deadline

The Chicago Cubs have approached the last two trade deadlines in very different ways, but they might end up disappointed with the results of both.

CHICAGO, IL - Starting pitcher Matt Garza of the Chicago Cubs delivers the ball against the Arizona Diamondbacks at Wrigley Field. (Photo by Jonathan Daniel/Getty Images)
CHICAGO, IL - Starting pitcher Matt Garza of the Chicago Cubs delivers the ball against the Arizona Diamondbacks at Wrigley Field. (Photo by Jonathan Daniel/Getty Images)
CHICAGO, IL - Starting pitcher Matt Garza of the Chicago Cubs delivers the ball against the Arizona Diamondbacks at Wrigley Field. (Photo by Jonathan Daniel/Getty Images)
Getty Images

Last year at the non-waiver trade deadline, the Chicago Cubs were 42-65. They entered that Sunday with a five-game losing streak, 16½ games back. The were the antonym of contender. Other than maybe Starlin Castro, there shouldn't have been a player on that team who wasn't on the trading block. It should have been a fire sale. Then they should have put the fire-sale ashes in some mud and sold it all to fancy day spas for $50 an ounce. The Cubs should have been sellers.

Instead, Cubs fans were treated to headlines like this:

Cubs’ Baker: Not for sale

And you starting thinking … Baker, Baker … the Cubs have Scott Baker? Wait, no, he's on the … oh, the manager. Wait, no, he's with the Reds, and you probably wouldn't see a manager switch teams at the deadline. Huh.

It was Jeff Baker. The Cubs weren't going to trade Baker, who's been good for between 200 and 299 at-bats for each of the last four seasons. He's a utility player -- the gleaming hood ornament on the Ford Aspire of bad teams. If the Cubs could have turned him into a C+ prospect, they probably should have done it.

Instead, the 2011 deadline came and went with only Kosuke Fukudome getting traded, and the Cubs had to eat almost all of his salary to make even that trade happen.

Turns out this is because GM Jim Hendry was a lame duck. He was effectively fired, and the owners didn’t want him to make any big moves on his way out. He was an ex-spouse sleeping on the couch until he found a studio, trying not to get in the way. It was an awkward situation all around, and you certainly can’t have a guy like that making huge decisions on a trade return for Jeff Baker.

To be fair, there was some question about whether or not Aramis Ramirez was willing to waive his no-trade protection. Even considering that, it was a quiet deadline. Carlos Pena, Marlon Byrd, Geovany Soto, and Matt Garza all stuck around. Pena left as a free agent. Byrd was traded after a 1-for-349 slump sucked the trade value right out of him this year, and the same thing might have happened to Soto, who's hitting just .186/.273/.335.

That inactive deadline was last year, though. It's a new era. Jed Hoyer and Theo Epstein aren't shy about making big deals, and they were ready. Excited, even. They had two huge trade chips in Ryan Dempster and Matt Garza. They were going to get a bushel of prospects. Possibly even several pecks along with them. Maybe even a coomb, if everything broke right.

They started with Dempster, and the Cubs agreed to a trade for one of the Braves' best young pitchers, 22-year-old Randall Delgado. It was a coup. It was a trade that would have made up for the inactivity of last season. Delgado was the #46 prospect in baseball coming into the season according to Baseball America. For three months of Dempster? An absolute coup.

Dempster nixed the deal. He’d rather to go to Los Angeles.

Okay, fine. That’s a right he’s earned as a veteran, as a 10-and-5 man. He can veto trades. Great, fine, whatever. The Cubs then reportedly offered Dempster straight up for Allen Webster. He’s a lesser prospect than Delgado, but still a good catch.

The Dodgers, realizing they had the leverage, declined. Their counteroffer of a Juan Uribe-signed 8"x10" wasn't accepted. The two teams are still hoping to meet somewhere in the middle.

Okay, dammit. The Cubs still had a huge trade chip to deal in Garza. And with a lot of teams not sure about selling because of the second Wild Card, Garza was the Cubs' trump card -- the only top-of-the-rotation pitcher signed through next year. Why pay a premium for Zack Greinke when you can sweeten the deal and get another year of Garza?

dammit so much i mean

The Cubs might get something for Alfonso Soriano if they chip in most of the $42 million he's still owed. They might get a token prospect for guys like Soto or David DeJesus. Bryan LaHair has hit .231/.291/.350 over the last two months, striking out in more than a third of his plate appearances, but he might interest a team as a cost-controlled platoon option. And, hold on here, even Jeff Baker might be on the table.

But for the second straight deadline, the Cubs are getting hosed. The first time was a mess of their own making. This year, it’s a mess of circumstance and misfortune. It’s almost as if the Cubs are cursed, but I don’t want to get controversial here. No, no. It’s a heckuva spot of bad luck, though, however you want to frame it.

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