Chicago Cubs Named Realistic Landing Spot for Jack Flaherty in Free Agency

Free agent Jack Flaherty was recently named a realistic target for the Chicago Cubs this winter.

Oct 30, 2024; New York, New York, USA; Los Angeles Dodgers pitcher Jack Flaherty (0) pitches during the first inning against the New York Yankees in game four of the 2024 MLB World Series at Yankee Stadium. / Brad Penner-Imagn Images

It has been a really strong offseason so far for the Chicago Cubs, and this is a team that is still looking to get better. 

After a good, but not great campaign in 2024, the Cubs are making splashes this winter to get themselves back into contention in the National League. 

So far, the biggest move for Chicago was the bold decision to trade for Kyle Tucker.

While the deal does come with some risk, Tucker makes the Cubs a much better team in 2025 and shows a willingness to seriously compete this year. 

While the acquisition of the talented outfielder makes the team much better, they still have a couple of other needs to address, one of which is in their starting rotation.

Even though Chicago had a strong starting staff last season, they could use one more top-end player to solidify the unit. 

Recently, Zachary D. Rymer of Bleacher Report spoke about the most realistic signing to fix the rotation for the Cubs and mentioned Jack Flaherty as their guy. 

“The Kyle Tucker trade gives the Cubs the superstar their lineup had been lacking. They don't truly need much else, but one's ears perked up when Sahadev Sharma of The Athletic wrote on December 9 that Flaherty interests the Cubs. Flaherty could cost nine figures, but the Cubs can sign him and likely still come in below the $241 million luxury-tax threshold for 2025. And if they do it, they'll have an elite rotation with which to chase an NL Central title.”

The addition of Flaherty would be a nice upgrade to Chicago’s rotation, as the right-hander had an excellent 2024 campaign.

With the Detroit Tigers, the 29-year-old totaled a 7-5 record and 2.95 ERA before being traded to the Los Angeles Dodgers. 

With the Dodgers, Flaherty continued to play well, as he helped them win the World Series as one of their top pitchers. 

Because of this, Flaherty will be receiving a much larger contract this winter after he had to take a one-year prove-it deal last offseason after he struggled in 2023.

For the Cubs, the addition of Tucker has certainly put them in a win-now mindset for 2025.

Due to the talented outfielder being a free agent at the end of this upcoming campaign, there is no guarantee he will be in Chicago for more than a year.

This makes winning even more important. 

Furthermore, there is certainly a path to winning the NL Central this coming season, with the Milwaukee Brewers likely taking a step backward after losing Devin Williams and Willy Adames. 

With the goal of competing in 2025, the addition of Flaherty would certainly help improve the starting rotation.