Despite their victory in the 2024 World Series, the Los Angeles Dodgers made offseason roster upgrades. The addition of pitcher Blake Snell is part of this, which probably implies Jack Flaherty will be leaving in free agency. Although this would seem like a terrible thing for him, it gives Flaherty access to a very competitive market in free agency. Although the New York Post’s Jon Heyman estimates that Flaherty will sign for $80 million, he might actually sign for more.
It was recently suggested by Bleacher Report’s Tim Kelly that the Chicago Cubs would try to sign Flaherty in free agency. According to Kelly, the Cubs aren’t seen to be a major candidate to sign him. However, they could enter the race with ease. “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,” wrote Kelly. However, after recovering from Tommy John surgery, Boyd made eight starts the previous season. Despite having a history in the bullpen, Javier Assad fared well out of the starting rotation last season and may eventually return to relief.
Shota Imanaga, Justin Steele, and Flaherty at the top of the starting rotation would generate a lot of excitement for the Cubs going into a season that they hope will see them make the playoffs for the first time since 2020. Flaherty wouldn’t be a bad addition, even though the Cubs don’t need a starter. The Cubs may confidently place him at the top of their rotation because he is a very reliable starter. Chicago can spend money, particularly if they trade a deal like Jameson Taillon for the previously stated Flaherty. It wouldn’t be shocking if the Cubs made a last-ditch attempt to get Flaherty to Wrigley Field, even if Chicago won’t be the front-runners to sign the righty.
