The Chicago Cubs beat the Milwaukee Brewers to Clay Holmes at the trade deadline, and won a two-time All-Star with a 3.26 ERA since the start of 2025 who hadn’t thrown a major-league pitch since May. Chicago got Holmes and outfielder Tyrone Taylor from the Mets for infield prospect Jefferson Rojas, but the pitcher himself arrived three rehab starts into a comeback from a fractured right fibula — with a return date no earlier than mid-August.
That’s a bidding war won for a pitcher nobody has actually seen throw a pitch this year.
Chicago didn’t stop there. The front office also added All-Star starter Kevin Gausman from the Blue Jays and left-hander Braxton Garrett from the Marlins, then flipped longtime fan favorite Moises Ballesteros and pitching prospect Mason McGwire to the Angels for reliever Ryan Zeferjahn, a 97th-percentile strikeout arm under club control through 2030. Across the whole deadline, six players who ranked in MLB Pipeline’s Top 30 left the organization.
I spent two years freelancing at fifty dollars a story before anyone paid me a real rate, and that math never fully leaves you. Every time a team spends this much on a player it hasn’t actually seen play yet, I do the same thing in my head: what did you just buy?
The market for Holmes was real. Milwaukee was pushing hard, so were the White Sox and Braves, and a separate agreement between the Mets and Diamondbacks reportedly collapsed on medical review just hours before the deadline. Chicago won the auction anyway, for a starter who was still on the injured list when the trade closed.
Giving up Ballesteros for that only makes sense if Milwaukee was going to sit still.
Milwaukee didn’t sit still. The Brewers pulled Dustin May and JoJo Romero out of St. Louis in a rare in-division trade, adding a starter and a reliever of their own the same week Chicago was still unpacking its own haul. Milwaukee leads the current NL Central standings at 69-43; Chicago sits five and a half games back at 64-49.
Jed Hoyer’s front office has been aggressive all summer, going back to the Skubal chase Chicago lost out on a few weeks ago. This time he actually closed the deal. Winning an auction and winning a division are two different competitions, and Chicago just proved it’s better at the first one.
https://twitter.com/JonHeyman/status/2084379965605171556
None of that settles anything by itself. Milwaukee still has the better record, and the rest of deadline week only sharpened the contrast between a team adding depth around a division lead and one betting a fan favorite that an injured arm turns into October pitching.
Chicago won the trade. Milwaukee still might win the division.
