Chicago Cubs Miss Out on Ideal Free Agency Target To Boost Their Rotation

Another possible free agent addition for the Chicago Cubs is now off the market.

Oct 30, 2024; New York, New York, USA; Los Angeles Dodgers pitcher Jack Flaherty (0) reacts after giving up a home run during the second inning against the New York Yankees in game five of the 2024 MLB World Series at Yankee Stadium | Wendell Cruz-Imagn Images

The Chicago Cubs have been active this offseason, but it hasn't come via free agency.

While the front office has brought in solid bullpen options and starting pitcher Matthew Boyd with low-end commitments, the true splashes have come from aggressive trades, landing both Kyle Tucker and Ryan Pressly in separate deals with the Houston Astros.

Tom Ricketts made his stance known when it comes to their financial situation, so expecting the Cubs to be top spenders when he has not shown a willingness to consistently exceed the luxury tax is unrealistic at this point.

But they also missed a golden opportunity to boost their starting rotation further.

Per Jeff Passan of ESPN, Jack Flaherty and the Detroit Tigers agreed to a two-year, $35 million contract late Sunday night. The deal is frontloaded with $25 million set to be paid in 2025, while 2026 is a player option for $10 million that can reach up to $20 if he makes 15 starts.

This is a deal Chicago could have been all over for themselves.

While $25 million AAV is a pretty penny for someone who bounced back in 2024 after two below average seasons in a row, the Cubs also have a clear need for a top-end right-handed starting pitcher in this rotation.

They're rumored to be a possible suitor for Dylan Cease, and while his 2025 salary is roughly $11 million less than what Flaherty is going to get this year, landing the former Cy Young runner-up is also going to cost them some assets with no assurance they'll be able to keep him around for the long haul since he's scheduled to hit the open market after this season.

So, Chicago missed out on another ideal free agent target, this time one that wouldn't have broken the bank to sign.