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Astros' perfect trade deadline target could emerge thanks to Cubs' shocking collapse

Hey, it could HAPPen.
May 28, 2026; Pittsburgh, Pennsylvania, USA;  Chicago Cubs left fielder Ian Happ (8) hits an infield single against the Pittsburgh Pirates during the sixth inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images
May 28, 2026; Pittsburgh, Pennsylvania, USA; Chicago Cubs left fielder Ian Happ (8) hits an infield single against the Pittsburgh Pirates during the sixth inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

A few weeks ago, pitching the Houston Astros as deadline buyers would've gotten you laughed out of the room. The team was 16-27 and circling the drain.

Things look a little different now, with an emphasis on "a little." Houston has clawed its way back toward respectability, and with the deadline still seven weeks out, the conversation has quietly drifted from "who do they sell?" toward "what could they actually use?" That doesn’t mean they’ll be buyers when that time comes, but it’s at least a possibility.

Thanks to the Cubs drifting toward the bottom of their standings, an option has emerged who could help the Astros in a big way.

Cubs' collapse could make Ian Happ an Astros trade deadline target

The Cubs were supposed to be a problem for the rest of the National League this year. On May 8, they won their 10th game in a row for the second time in the first 39 games of the season. They were 27-12 and 3.5 games clear of second place. But the bottom fell out. They’ve had a 10-game losing streak to match one of the 10-game winning streaks. Through the weekend, they hadn’t won more than two in a row since the 10-game winning streak. They’re 7-20 in that time. They’re still in the hunt for both the division and the Wild Card, but they’re going the wrong way.

Going the wrong way can sometimes change the way a front office thinks. One name that may not be all that likely today, but should be filed away, is Ian Happ. While he has wanted to stay a Cub and has a no-trade clause, he did admit before the season that “another chapter elsewhere” is plausible. Yes, that was more about free agency, but once a player sees himself potentially elsewhere, it becomes easier to see a trade as a possibility.

Happ does have that full no-trade clause, but maybe it’s a bit more likely that he agrees to a deal, especially if he has a chance to put up numbers and chase a title. Houston’s outfield has been a struggle for a couple of years now. They’ve tried Jose Altuve. That didn’t work. They tried acquiring Jesus Sanchez at the deadline last year. That didn’t work. They’ve put Yordan Alvarez in left field periodically because that’s what he wants, but that’s tough for a guy who really just needs to hit. 

Happ is kind of the exact shape of the cure. He’s a switch-hitter, so he helps provide the lefty bat while also never being at a platoon disadvantage. He’s won four Gold Gloves and continues to rate well in left field, though he’s been much closer to average this season. And, offensively, he’s been basically himself and maybe even a little bit better.

The downside of Happ is that he will strike out. But he also works walks as well as just about anyone. And he has legitimate power, which has been more present this year than in the past. Happ won’t wow you with batting average, but he gets on base and he drives the ball. It would be a lie to imply that he’s a star, but he’s very consistent with what he provides. And on a team like the Astros that already has the star hitter in Alvarez, they really could use consistency as a second or third fiddle.

The catch, and it’s a big one, is that the Astros need to be buyers first. They’re 30-37. They have clawed out of the early hole, but being less bad isn’t the same as being good. There is a real world where Houston spends the rest of June and all of July weighing whether they should sell or shop. It could be that the powers-that-be determine that the future of the Astros outweighs a potential run at a third Wild Card, and they do decide to start moving valuable pieces.

It may or may not be real, but it is the perfect kind of speculative. If the Cubs keep falling and the Astros keep rising, and if Happ decides being in a contender’s lineup beats losing, sure, it’s possible. That’s a lot of ifs. But the fit is clean. A switch-hitting, Gold Glove left fielder on an expiring contract who can slot into the exact hole the Astros have been unable to fill would be pretty great.

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