MLB insiders continue to link Brewers to top 2026 trade deadline candidate

18 years ago, the Milwaukee Brewers took a massive leap and landed CC Sabathia to get the team to its first postseason appearance since the 1982 World Series. Landing Sabathia took a pretty hefty toll, as it cost then-top prospect Matt LaPorta, as well as a host of other prospects, and a player to be named later that ended up being Michael Brantley, who went on to make five All-Star Game appearances.

However, in the short term, the move paid off, as the Brewers reached the postseason for the first time in nearly three decades and re-energized a fanbase that had suffered a prolonged period of losing.

Now Milwaukee faces a pair of new and more daunting obstacles: the Los Angeles Dodgers and a return to the World Series. The Brewers have been close a couple of times, before being ousted in the NLCS by Los Angeles in both 2018 and 2025. Could it take another franchise-altering move to get over the current hump? Some MLB insiders are saying that it is time for the Brewers to strike.

The baseball world is strongly urging the Brewers to go "all-in" for Tarik Skubal this summer

Last week, Ken Rosenthal was on Foul Territory and said that while he doesn't think the Brewers will actually go "all-in", they do have the pieces to land Detroit Tigers' ace Tarik Skubal, who is by far the best name available on the trade market this year.

Then on Monday, Joel Sherman of MLB Network outright said that Milwaukee needs to go get Skubal.

On Thursday morning, Jeff Passan of ESPN released his early trade deadline preview, and once again the Brewers' "top target" was none other than Skubal. Three of the top insiders in MLB have already suggested the Brewers take a chance and trade for Skubal this year, and it's only June 5.

So how realistic would this be? Skubal is in a similar place as Sabathia was, as he is a pending free agent on a struggling team. The Tigers, who were expected to be a World Series contender in 2026, went 6-22 in the month of May and are currently 10.5 games back of the Cleveland Guardians in the AL Central. They are on the hook for Skubal's record-breaking $32 million deal that he won in arbitration, and could land a massive haul of prospects if they do elect to trade him away. In other words, it's very feasible that Skubal gets dealt before the midseason trade deadline.

The question then becomes: how likely are the Brewers to actually go "all-in" and trade for the reigning back-to-back AL Cy Young Award winner?

"All-in" is counterintuitive to the Brewers' current way of operating. Under the guidance of David Stearns and Matt Arnold, which has produced Milwaukee's ongoing "Golden Age," the Brewers have prioritized sustained success or "bites of the apple" as opposed to sacrificing potential long-term value for short-term success. The closest thing Milwaukee has done to going "all-in" was their 2018 season, when they not only signed Lorenzo Cain and traded for Christian Yelich in the offseason, but they were also more aggressive at the trade deadline than they have been since.

At the 2018 trade deadline, Milwaukee added two All-Star infielders in Mike Moustakas and Jonathan Schoop, and while trading for the latter didn't work out for the front office, the Brewers ended up within one game of a World Series appearance -- their nearest miss since they made the Fall Classic in 1982. Such evidence would seem to suggest that there is some merit to going "all-in," especially since Milwaukee was able to continue fielding competitive teams in the years after 2018.

Here's the issue: Skubal is going to cost far more in prospect capital than Moustakas or Schoop did back in 2018. The Brewers will realistically have to part ways with at least one Top 100-caliber prospect (more likely two) to acquire the Tigers' ace. While Jesús Made, Luis Peña, and Cooper Pratt are all practically untouchable, Jett Williams or Luis Lara (or both) could headline a package for Skubal. Assuming a few other names would be included in the deal as well, that's a lot to give up for roughly two months and a postseason run of Skubal. Pair that with the fact that Skubal is coming off of an elbow procedure, and it looks like an even riskier move for the Brewers to make.

The flip side of the argument, however, is that Milwaukee's farm system has never been stronger than it is right now. The Brewers could stand to deal one or two top prospects from their minor league system and still have one of the strongest farms in all of baseball.

There's plenty of time before the trade deadline, and a lot needs to happen before the Brewers seriously consider adding Skubal to their rotation, including the Tigers' ace proving that he's healthy and can impact a contending team's postseason run. However, the fact that several insiders are already building momentum for Milwaukee to have an aggressive trade deadline bodes well for fans of the Brewers, who generally play things safe at the midseason deadline.

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