A Matt Shaw trade is still a scenario, not a reported negotiation. But it is an easy one to picture this winter: move a blocked infielder, land a starter and patch the rotation. The harder question is what the Chicago Cubs would have left to pay with after a deadline that already cost them four young players.
Sports Illustrated's Doug Schwamb floated the idea this week, suggesting Shaw could headline a deal for Los Angeles Angels left-hander Reid Detmers while admitting Shaw alone would not be enough. No report has the Cubs and Angels discussing it. That admission, though, is where the real debate starts.
Chicago gave up four young players across two deadline trades. Catcher Moisés Ballesteros and right-hander Mason McGwire went to Anaheim for reliever Ryan Zeferjahn, according to MLB.com . Ballesteros was Pipeline's No. 1 Cubs prospect entering the year. McGwire, ranked 18th in the system, had made the Futures Game. A day earlier, Chicago landed Kevin Gausman from Toronto for Brett Bateman and Ty Southisene .
That is a lot of young talent for one deadline, and the rotation questions that were already circling have not gone away. The season ended in a Wild Card sweep, and the starters are still the biggest hole.
Shaw is 24, was the 13th overall pick in 2023 and has 18 home runs and 68 RBI over 185 career games. He played 77 games in 2026 and hit five home runs, squeezed by Alex Bregman's arrival at third base. Inside the Cubs' roster, that looks like a super-utility role. To a rebuilding team, it could look like a former top pick with room to grow.
That is what would make a Matt Shaw trade workable on paper. It also means he could not carry the price by himself.
Detmers is 27, was paid $2.625 million this season and is under team control through 2028, according to ESPN's David Schoenfield in July. Multiple sources told Yahoo Sports' Russell Dorsey before the deadline that the Cubs were interested, so he's not a new name on their board. That said, nothing suggests the Angels have made him available. A starter with that much control is unlikely to leave for one prospect.
Jul 28, 2026; Anaheim, California, USA; Los Angeles Angels pitcher Reid Detmers (48) throws against the Houston Astros during the fifth inning at Angel Stadium. Mandatory Credit: Gary A. Vasquez-Imagn Images
Schwamb pointed to James Triantos, Jaxon Wiggins, Caden Sorrell and Kane Kepley as other top prospects worth monitoring in a deal like that. If a Matt Shaw trade needed two or three of those names attached, the Cubs would be spending the same kind of capital they spent in August, with less of it left.
Chicago's own pitching group is unsettled. Justin Steele is coming off elbow trouble, Javier Assad's role is still undefined , and Schwamb noted that Gausman, Clay Holmes and Shota Imanaga could all leave. Spending the last good prospects on one arm leaves little cushion if those internal bets miss, a concern that already shapes how the Cubs have to manage their starters .
The case for a Matt Shaw trade, if it ever gets that far, is real: he's young, versatile and blocked, and Detmers would give Chicago a controllable starter it badly needs. But the price matters as much as the player. After giving up four young players in August, the Cubs cannot treat their remaining prospects as an unlimited line of credit.
The open question is whether the Angels would even entertain Shaw plus a lighter package, or whether the ask would grow past what Chicago should pay. If it does, the better winter plan may be the slower one: sign a starter, trust the internal arms and keep Shaw's value for a deal that fits.
Main Photo: Pablo Robles-Imagn Images
