Cubs Rumors: Jim Bowden sees Cubs, Astros as trade deadline match made in heaven

With the Cubs headed toward selling at the trade deadline, it's not hard to see how Chicago matches up with the reigning World Series Houston Astros as trade partners.
League Championship Series - New York Yankees v Houston Astros - Game Six
League Championship Series - New York Yankees v Houston Astros - Game Six / Tim Warner/GettyImages

If you haven't already, come to terms with it. The Chicago Cubs, in all likelihood, are going to be sellers - not buyers - at the Aug. 1 MLB trade deadline.

It's a tough pill to swallow. From 2015 to 2020, the fanbase grew accustomed to winning - something, frankly, that was a rarity on the North Side for generations of fans. But since then, it's been back to the old ways and the long-held 'Lovable Losers' moniker is quickly making a comeback.

Since the start of the 2021 season, the Cubs are just 190-229 and haven't even reached the postseason during that stretch. The core - and surrounding cast, for that matter - of the 2016 World Series championship-winning team was scrapped and sold off, leaving only Kyle Hendricks on the team at this point. And, who knows - maybe his days are numbered, too.

But with the Cubs poised to sell again, it's all eyes on Jed Hoyer and Carter Hawkins. The patience and good will of fans is spent: any trades made need to pay off at a big league level in 2024. Jim Bowden of The Athletic believes the team that could be a perfect fit, the Houston Astros, might even be willing to part with their #1-ranked prospect in outfielder Drew Gilbert in a deal.

"This type of huge rental blockbuster would cost the Astros dearly, in terms of extracting value from their farm system, but a trade like this would also position them to be able to catch the Rangers in the AL West and, more importantly, give them a legitimate shot at back-to-back-to-back World Series appearances."

Jim Bowden, The Athletic

Bowden singles out both Marcus Stroman and Cody Bellinger as targets - and it's a similar proposal we broke down earlier in the week, looking at the surging Baltimore Orioles and their embarrassment of position player prospect riches as a potential fit in a trade. But looking at the Astros and Gilbert, it's worth wondering if this is the path that makes the most sense given the Cubs' logjam in the outfield moving forward, as well.

Cubs, Astros don't fit as well as Jim Bowden suggests in his piece

Chicago has Seiya Suzuki and Ian Happ under team control through 2026. Top prospect (ranked #7 in all of baseball by MLB Pipeline)Pete Crow-Armstrong could seize the starting job in center field and begin his quest to fill his trophy case with Gold Glove Awards as soon as next season. Kevin Alcantara and Alexander Canario could also factor into the outfield picture at some point.

Gilbert ranks 70th in the top 100 rankings, according to MLB Pipeline - by no means a lesser talent when you're looking at the big picture, but the fit is questionable for me. Even if Baltimore balks at the idea of unloading Heston Kjerstad, pivoting to a package around another Orioles top 100 guy like Coby Mayo makes more sense to me personally.


Stroman and Bellinger will be among the most highly sought-after pieces in the weeks and days leading up to the deadline. It's a deadline that carries major risk for the Cubs, who desperately need to return to contention to fill Wrigley Field and draw ratings on Marquee. More far-off prospects won't satiate anyone and anything less than major pieces that are near-big league ready will be considered a failure by many.