The Los Angeles Dodgers won the 2024 World Series, but that didn’t stop them from upgrading their roster during the offseason. This includes adding pitcher Blake Snell, which likely means Jack Flaherty is headed out the door in free agency. While this seems like a bad thing for him, it opens up the door for Flaherty to have quite an aggressive market in free agency. Jon Heyman of the New York Post projects Flaherty to sign for $80 million, but he may end up signing for more than that.

Tim Kelly of Bleacher Report recently suggested the Chicago Cubs could enter the race to acquire Flaherty in free agency. Kelly noted how the Cubs aren’t viewed as a serious contender to acquire him, but they could easily jump into the race. “With Chicago having already signed veterans Matthew Boyd and Colin Rea, the guess here is the Cubs won’t make another move in the starting rotation,” Kelly wrote. “But Boyd made eight starts last year as he returned from Tommy John surgery. Javier Assad pitched well out of the starting rotation last season but has a history in the bullpen and could be shifted back to relief at some point.

“A starting rotation headlined by Shota Imanaga, Justin Steele, and Flaherty would give the Cubs a lot of buzz heading into a season they hope will send them to the playoffs for the first time since 2020.” While the Cubs don’t need to add a starter, Flaherty wouldn’t be a bad acquisition by any means.

He’s a very consistent pitcher who the Cubs could confidently stick at the top of their rotation. Chicago has the money to spend, especially if they offload a contract like Jameson Taillon to replace with the aforementioned Flaherty. While Chicago isn’t going to be the favorites to sign the righty, it wouldn’t be surprising to see the Cubs make a last-minute effort to bring Flaherty to Wrigley Field.