Time to Catch Up: After Brewers Win World Series, Cubs Have Their Assignment

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The Brewers are absolutely never stagnant. That's the greatest lesson the Cubs can learn from their chief rivals, as they attempt to recover from a decade-long stretch of domination by Milwaukee that culminated in a championship Wednesday. Jed Hoyer's greatest shortcoming as a team builder is an insufficient comfort with rapid change. His Milwaukee counterpart, Matt Arnold, never forgets to keep his roster moving.

Every front office makes regrettable moves, whether because the process was faulty or simply because of bad luck. Not long after Isaac Collins finished fourth in National League Rookie of the Year voting last year, the Brewers shipped him and reliever Nick Mears to the Royals in exchange for lefty reliever Angel Zerpa. Though he was instrumental in Team Venezuela's win in the World Baseball Classic, Zerpa only made 12 appearances for the Brewers (lousy ones, too) before needing Tommy John surgery. There will be duds. Hoyer has always feared those duds; that fear has stopped him from making many moves. He would never have traded Collins when Arnold did, so he would have avoided a mistake—although, again, Arnold's process might have been right.

However, Arnold also traded Caleb Durbin back in February. Durbin finished one rung above Collins in Rookie of the Year voting last year, but the Brewers sent him packing, even though they didn't have a clear plan to backfill third base. In exchange, they landed Kyle Harrison, Shane Drohan and David Hamilton. Harrison was the team's co-ace in the first half; Drohan was a vital fill-in for the rotation in the middle of the season; and Hamilton finished with nine hits (two of them home runs) and 0.042 Championship Win Probability Added in October. Hoyer also never would have made that trade.

Those are just two examples. They're extreme cases, too, and not wholly fair to Hoyer. The Cubs have, to their credit, been more active lately, as they learn by watching the Brewers trounce them year after year. In 2025, Hoyer was conservative at the trade deadline. In 2026, he first agreed to a double-acquisition of Reid Detmers and Ryan Zeferjahn, then (when the initial deal fell apart) pivoted and added three other players in two other deals, in addition to grabbing Zeferjahn. He made the Michael Busch trade. He made the Kyle Tucker trade. He signed Alex Bregman. He's evolved over the course of his tenure as the top baseball decision-maker; he's better than he was.

Still, though, the Cubs change slowly. They invest in veterans, but that means less investment in player development and less pressure on everyone to consistently excel at that essential task of every organization. Fewer resources are allocated to scouting. Fewer interesting possibilities even occur to them. Part of Hoyer's pivot toward greater aggressiveness has been locking up his own players on long-term deals. The Pete Crow-Armstrong deal is an all-timer—a huge win. The Nico Hoerner deal, however, looks lightly regrettable. Both deals locked a player into the team's long-term firmament and made it harder for them to rapidly change, which they need to do. The Brewers are far ahead of them, and there's every chance they'll get even further ahead. They're younger; they're deeper. The Cubs can't keep up by relying on Crow-Armstrong, Bregman, Hoerner and Dansby Swanson as much as they did this year.

The good news, of course, is that change has come to Hoyer's doorstep. He doesn't have to search very far for impetus to do it. The whole starting rotation from the end of the season are now, officially, free agents. So are Ian Happ and Seiya Suzuki. So will be Carson Kelly. The Cubs have no choice but to change. The challenge, for an executive who has always preferred stability, is to replace his horde of outgoing players with ones who are as good or better, but also younger and more loosely held. More aggressive short-term deals might make sense. Unexpected trades (for instance, sending Matt Shaw and Pedro Ramírez to interested suitors in exchange for players like Zerpa, Harrison, Drohan and Hamilton) might make sense. One way or another, Hoyer has to engage in high-risk, high-variability roster-building. He might fall off that tightrope, but if he never gets onto it, the Cubs won't be crossing the ravine between them and the Brwwers, anyway.

Comfort and ease are luxuries afforded only to big-market teams. The Brewers have gotten so good at living without them, though, that they've now denied those luxuries to the Cubs. Chicago has to get uncomfortable. They have to make changes that come with more acknowledged risk. If they don't, the next half-decade is going to look exactly like the last one, in Milwaukee and on the North Side of Chicago.