Why the Brewers can't afford to follow the Red Sox' aggressive offseason strategy

After a disappointing offensive performance against the Los Angeles Dodgers in the National League Championship Series, many Milwaukee Brewers fans have been calling for the front office to add an impact bat to the lineup ahead of the 2026 season. With a need for more power, a tool that doesn't come cheap in today's game, the Brewers are likely to turn their attention to the trade market when trying to find a bat who could legitimately change the entire dynamic of their offense.

Such a trade might seem far-fetched or idealistic, but the Brewers have the necessary resources to pull off a blockbuster this offseason should they elect to stray from their "sustained success" approach and veer towards "all in" land. With one of, if not the best farm systems in all of baseball and troves of talented, controllable starting pitching, it's possible that Milwaukee could construct a trade package for an impact bat that doesn't hamstring them too severely in the years ahead.

The reality is made even more likely by the fact that teams around the league are using their young starting pitching to bring in win-now players who don't offer nearly the same long-term value. In fact, one team has already done so on several occasions: the Boston Red Sox.

With the Red Sox' former President of Baseball Operations, Chaim Bloom, now leading the St. Louis Cardinals' front office, the two teams have already linked up for two major trades this offseason, which were aided by the fact that the two organizations find themselves in completely opposite positions this offseason; the Cardinals have entered a rebuild and the Red Sox are looking to build on their 2025 postseason appearance. Already St. Louis has sent both Sonny Gray and Willson Contreras to the Red Sox (in separate trades) and each time Boston has parted with one of their talented young starting pitchers to get the deal done. The Red Sox gave up 26-year-old Richard Fitts and top pitching prospect Brandon Clarke to acquire Gray, and sent 26-year-old Hunter Dobbins in the deal to acquire Contreras.

It might seem like a formula the Brewers could easily replicate, flipping some of one or two of their young starters for a former All-Star, but there's a reason a big-market team like the Red Sox can afford to part with future value while Milwaukee must keep one eye on the future at all times.

Brewers can't afford to trade away controllable starting pitchers for impact players like the Red Sox are doing

With multiple players from the group of Chad Patrick, Tobias Myers, Logan Henderson, and Robert Gasser set to serve as starting pitching depth in 2026, it's natural to expect the Brewers to follow the Red Sox' strategy and trade one or multiple of them for players who can help the team win in 2026.

However, Boston trading away young, controllable starting pitchers is different than the Brewers doing so. In future seasons, when Boston would have relied on players like Fitts and Dobbins, whom they traded away this offseason, the Red Sox have the payroll space to replace such players with free agents, who cost far more but offer a similar output on the field. The Brewers don't have the same luxury.

Having starting pitchers in the first five years of their MLB careers, who not only cost less but are also often in their physical prime, is more valuable to the Brewers, who rely on finding surplus value in their young stars as a way to remain competitive with teams who have a payroll two or even three times the size of theirs.

Next season, the Brewers are likely to lose both Freddy Peralta and Brandon Woodruff when each hits the open market and commands a contract outside of Milwaukee's budget. Having all of the starters listed above alongside Quinn Priester and Jacob Misiorowski in their rotation for a fraction of the price of what they would be worth on the open market is not just a huge asset for the Brewers; it's a necessary one if they want to remain competitive.

Therefore, while it might seem like the Red Sox are laying the foundation for the offseason that the Brewers should want this winter, the controllable starting pitching that Boston is trading away to improve their 2026 roster is far more valuable to a team like the Brewers, who can't replace them with free agents in future seasons.