Yankees Have One Scary Dilemma Heading Into the MLB Season

The New York Yankees will open the 2026 MLB campaign against the San Francisco Giants on Wednesday night featuring a very similar roster to last season. The lineup is basically identical, and the starting rotation features mostly familiar faces (other than Ryan Weathers). But there is one area in which the Yankees have had some turnover, and it's perhaps the biggest problem on their roster: the bullpen.

New York lost key relievers Devin Williams and Luke Weaver to free agency (to the Mets, because, well, Steve Cohen) and didn't really replace them. Yes, the Yankees still have a good back end of the pen headlined by David Bednar, Camilo Doval and Fernando Cruz, but questions remain otherwise. Rule 5 draft pick Cade Winquest made the team in spite of posting a 7.

20 ERA in Spring Training, which was interesting. Jake Bird will also be a relief option after having been sent down following just three appearances in the Bronx last season. Can Tim Hill continue producing at the age of 36?

Will Ryan Yarbrough and Paul Blackburn replicate their success from 2025? Is Brent Headrick for real? New York Yankees pitcher Cade Winquest.