Trevor Megill and the Milwaukee Brewers are preparing for the World Series, but after that, he will enter a pivotal offseason.
Megill was an All-Star last season and has one more year on his deal before entering free agency. Despite how good he has been, his fate may already be sealed. The Brewers' last two star closers have both been traded before hitting free agency, and Megill could join Josh Hader and Devin Williams on a list of elite pitchers the Brewers have traded before hitting the open market.
It remains to be seen whether winning a World Series changes the way the Brewers do business, but it likely won't. If they do shop Megill, the New York Yankees should be all over it. The last time the Brewers traded a closer was Williams, and they sent him to the Bronx. Even though that did not work out great, the Yankees might not have a choice but to try again.
David Bednar is a free agent this offseason, and the Yankees are reportedly going to give him the qualifying offer. Should he decline and sign elsewhere, the team will have a huge hole in the backend of its bullpen. Megill has 81 saves and a 2.61 ERA since 2024. He, most importantly, has been just as good in the postseason.
Players who get traded to New York always seem to have question marks surrounding their ability to perform in a big market. Unlike Williams, Megill has thrived in the postseason, and that could be an indicator of his ability to play in New York. If he can do the job on the biggest stage in the biggest moments, perhaps the pressure of a big market won't impact him.