The clock strikes closer to 5 PM, and the pressure intensifies for the Chicago Cubs as Thursday’s trade deadline looms large. You know what they say about make-or-break moments? This is exactly what Jed Hoyer and his front office are set to achieve. With the Cubs sitting in the thick of a division race against the Milwaukee Brewers, every decision carries the weight of their World Series aspirations hanging in the balance.

Enter Shane Bieber, the Cleveland Guardians’ million-dollar ace, who’s suddenly become the hottest commodity on the trade market. Why are the Cubs circling like sharks, you ask? Well, the former Cy Young winner carries a $16 million player option for 2026 with a $4 million buyout, making him a $26 million guarantee for two years. But here’s the kicker – MLB insider Jeff Passan declared that Bieber is “almost certain to go before the deadline“, and his Tommy John recovery has made him more affordable than anticipated.

David Haugh’s passionate plea on 670 The Score perfectly captures the urgency surrounding Hoyer’s situation. “His mindset has to be big picture and long-term, with the World Series window open, and you need to prop it open a little bit wider today,” Haugh declared. The veteran sports voice didn’t mince words about the Cubs’ recent moves, stating that while “Andrew Kittredge will help the bullpen” and “Soroka will be a piece,” these acquisitions were “more underwhelming than over-the-top moves.” Tbh, it makes sense when Haugh emphasized what the Cubs truly need: “That’s not a guy that you envision being the type of guy you could be on the mound Game 1, two, or three of a playoff series. That’s what you need today. Go get him, Jed Hoyer.”

History has a funny way of repeating itself—until it doesn’t. The Cubs and Guardians danced around trade talks for years, never quite finding the right music. But desperation changes everything, doesn’t it? With Cleveland ready to sell and Bieber’s $14 million price tag suddenly looking like a bargain, this deadline feels different. The Cubs have already made moves, acquiring Andrew Kittredge for their bullpen and Michael Soroka for depth, but as Haugh emphasized, these feel more like band-aids than the surgical strike they need. The clock ticks toward 5 PM, and Chicago’s championship window hangs in the balance. Chicago’s answer lies in Cleveland. The Cubs face their moment of truth with Shane Bieber on the trading block.

Cubs Weigh Major Trade Risk for Shane Bieber

But here’s where the rubber meets the road. The Cubs face their biggest deadline decision: rolling the dice on Shane Bieber’s damaged arm. Chicago needs rotation depth desperately, and Cleveland dangles the former Cy Young winner like bait. But here’s the catch—Bieber hasn’t thrown a major league pitch since April’s Tommy John surgery.

Bieber demolished minor league hitters, striking out 14 in seven innings across lower levels, then delivered seven strikeouts with eight whiffs in his latest four-inning appearance. The Cubs see these flashes and dream of playoff magic. Yet rehab success rarely translates directly to October pressure.

Bieber carries a $10 million salary with a $4 million buyout on his $16 million player option for next season. For Chicago, this represents more than rental value—it’s a two-year window to compete. The Cubs calculate risk versus reward: acquire a proven ace recovering from surgery or watch division rivals strengthen their rotations.

Trade rumors intensify as Thursday’s deadline approaches, with the Cubs and Guardians rekindling negotiations that stalled during the offseason. Chicago’s front office knows waiting means losing Bieber to competitors. The question isn’t whether Bieber returns to form—it’s whether the Cubs can afford not to bet on his comeback.