Brewers Must Avoid Offering 1-Time All-Star Long-Term Deal

The Milwaukee Brewers, like a lot of other teams out there right now, have had some success getting early contract extensions done with core pieces.

The best example of this right now for the club is Jackson Chourio. While he hasn't played in a game yet this season for Milwaukee, he is just 22 years old and has looked like a superstar when he has been on the field for the Brewers. Plus, he's under contract for a long time. Brewers No. 4 prospect Cooper Pratt joined the mix this season by inking an eight-year deal just north of $50 million before even making his big league debut.

Early extensions can be great because they lock up core pieces for a long time and do actually save some cash in the long run, if the deal is a hit. For example, the Brewers made a little extra for Chourio to begin his career, but if he has a few more years just playing at the level he did in 2025, it will make the contract look like a steal in the long run. While this is the case, the Brewers shouldn't consider long-term extensions for everyone. For example, one player the Brewers should avoid handing a long-term deal to would be All-Star closer Trevor Megill.

The Brewers shouldn't offer a long-term deal right now

Mar 30, 2026; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Trevor Megill (29) delivers a pitch against the Tampa Bay Rays in the ninth inning at American Family Field. Mandatory Credit: Michael McLoone-Imagn Images | Michael McLoone-Imagn Images

When he is at his best, he can be among the top closers in the game. In 2025, he was an All-Star and recorded a 2.49 ERA and 30 saves. In 2024, he had a 2.72 ERA and 21 saves. Megill can be an awesome piece for this team. But the bullpen is volatile. So far this season he has an 11.25 ERA in five appearances.

He's under team control in 2027 before he hits free agency ahead of the 2028 season. But the Brewers have played this game before.

Remember Josh Hader and Devin Williams? It wouldn't be shocking to see the Brewers go in that direction once again after the 2026 season comes to an end. Abner Uribe is years away from free agency and could be the next guy on the list. So, while Megill is great overall, if there was one player for the team to not consider a long-term extension with right now, it would be him. Again, not because he's not a good player. Of course he is. But it's just not been a strategy the team has rolled with in the past and doesn't seem likely to change.