The Chicago Cubs have missed out on another ideal free agent target to improve their starting rotation. While the Cubs have been active this offseason, most of their moves have come through trades rather than free agency. The team has bolstered their bullpen and added starting pitcher Matthew Boyd on affordable contracts, but the major acquisitions have been through trades, including landing Kyle Tucker and Ryan Pressly from the Houston Astros.
Despite Tom Ricketts’ statements about the Cubs’ financial situation, which suggests they won’t be major spenders, they had a real opportunity to strengthen their rotation further. According to ESPN’s Jeff Passan, Jack Flaherty and the Detroit Tigers agreed to a two-year, $35 million deal late Sunday. The contract is frontloaded with $25 million paid in 2025, while 2026 features a player option worth $10 million, which could rise to $20 million if Flaherty makes 15 starts.
This was a deal the Cubs could have pursued. While the $25 million average annual value is a significant sum for someone coming off a couple of subpar seasons, the Cubs have a clear need for a top-tier right-handed starter. Though they are rumored to be interested in Dylan Cease, landing the former Cy Young runner-up would require giving up assets, and there’s no guarantee they’ll be able to retain him after this season, as he’s set to hit free agency.
In the end, the Cubs missed out on an ideal free agent opportunity—one that would not have broken the bank to sign.
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