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The baseball world is buzzing as the Chicago Cubs, locked in a dogfight for the postseason, are at the center of trade conversations involving right-hander Dylan Cease. For Cubs fans, the mere mention of Cease’s name conjures déjà vu, a pitcher initially lost in the notorious 2017 deal that sent him south to the White Sox for José Quintana. Now, as July’s trade deadline approaches, Chicago is exploring the possibility of reacquiring the talented starter, this time from the San Diego Padres.
In the summer of 2017, the Cubs, two years removed from their historic World Series win, pulled the trigger on a high-stakes trade. They sent a package centered on pitching prospects Dylan Cease and Eloy Jiménez to the White Sox, and in return, received lefty José Quintana. Quintana gave the Cubs solid innings, but Jiménez blossomed into a middle-of-the-order force, while Cease developed into one of baseball’s most electric arms. The trade has been a persistent ‘what-if’ for a fan base hoping their player development pipeline would yield rotation stars.
Cease’s success, most notably his runner-up finish for the AL Cy Young in 2022, compounds the regret. When the White Sox entered a rebuild, Cease was shipped to the Padres ahead of the 2024 campaign, where his flashes of brilliance continued, even through bouts of inconsistency.
Padres Listening, But Not Necessarily Selling
The twist in this trade deadline drama is the Padres’ position in the standings, they’re currently in the mix for a National League playoff berth. Despite this, reports indicate San Diego is willing to listen on offers for Cease. Their rationale? With Cease due to hit free agency after the season, and with no extension in sight, the Padres, stretched thin financially, may leverage the market scarcity of top-end starting pitching, seeking to address multiple roster holes in return.
A recent string of reports points to several teams showing interest: the Yankees, Red Sox, Mets, and notably, the Cubs. That isn’t to say anything is imminent. Insiders insist a deal remains a “major long shot,” especially since the Padres typically only shop rental players when the return solves immediate needs that bolster their current roster.
The Padres are listening on Dylan Cease, with the Yankees, Mets, Cubs and Red Sox among teams believed to have checked in. SD is a buyer but often listens on rentals. Major long shot!
— Jon Heyman (@JonHeyman) July 23, 2025
What Would a Trade Look Like?
For the Cubs, the motivation to pursue Cease is clear. They feature an effective top-two in the rotation with Shōta Imanaga and Justin Steele, but lack the frontline depth of National League juggernauts. Cease, with his high-octane fastball and strikeout pedigree, would transform Chicago’s pitching staff and inject legitimate ace potential down the stretch.
On Chicago’s side, any proposal for Cease will be painful. According to industry chatter, the Cubs have broached a package involving two premium prospects: catcher Moises Ballesteros and outfielder Kevin Alcántara, ranked fourth and sixth in the Cubs’ system, respectively. Ballesteros is a bat-first catcher quickly rising through the ranks, while Alcántara is a tooled-up outfielder who’s already seen big-league time. Reports confirm that the Cubs are unwilling to include blue-chip infielder Matt Shaw, and are instead enticing the Padres with depth and upside at positions of organizational need.
While the narrative of bringing Cease “home” tugs at Chicago’s heartstrings, there’s a calculated urgency at play. The Cubs’ window for contention relies on augmenting a core with an impact starter. Cease’s stuff, despite a rocky 2025 campaign that’s seen his ERA balloon to 4.59, remains tantalizing. Advanced metrics suggest his peripheral stats (notably an xFIP of 3.30) are far better than his surface numbers, indicating a measure of bad luck rather than decline.
The opportunity to secure a starter with true top-end talent, even as a short-term rental, is a risk a contending organization must consider. The Cubs’ farm system, deep with talent, gives them the ability to swing such a deal without mortgaging their future.
The Cubs will need to decide if their bid for Cease is a momentary splash for a pennant chase, or if they view this as a chance to extend him long-term, something that would lessen the sting of trading away two premium prospects.
Trade deadlines rarely proceed in a straight line, and as things stand, a Cease-to-Cubs reunion remains improbable. But the allure of bringing a former top prospect back, righting a historical wrong, and supercharging a rotation for the postseason is extraordinarily tempting. If the Cubs’ front office makes one last, aggressive push, they could bring the Cease narrative fully circular—giving fans the storybook ending they’ve long yearned for, or risking another chapter of “what could have been.”
