The Chicago Cubs are making bold moves this offseason, positioning themselves as serious contenders for star pitcher Jack Flaherty. With fierce competition from other MLB teams, the Cubs’ pursuit of Flaherty could solidify their rotation and reshape their aspirations for the 2025 season.
Flaherty: The most sought-after free agent pitcher still on the market
As the 2025 MLB offseason heats up, Jack Flaherty stands out as the top unsigned starting pitcher. The 29-year-old right-hander is coming off an impressive 2024 campaign, posting a stellar 3.17 ERA, a 1.068 WHIP, and 162 innings pitched across stints with the Detroit Tigers and Los Angeles Dodgers. Flaherty’s 13 wins last season tied him with prominent pitchers like Logan Webb and Michael King, underscoring his impact on the mound.
Flaherty’s consistency in 2024 marked a return to form after injuries hampered his performance between 2020 and 2022. Notably, his 5.9% walk rate in 2024 was a career low, showcasing his improved command. MLB insiders project Flaherty to secure a multi-year deal, with estimates ranging from three years and $63 million to five years surpassing $100 million. His proven track record and high ceiling have made him a highly coveted asset in an increasingly competitive market.
The Cubs’ strategic push for Flaherty
The Chicago Cubs have emerged as one of the strongest contenders in the race for Flaherty’s signature. MLB.com’s Mark Feinsand listed the Cubs among a handful of teams “in the mix” for the star pitcher, alongside the Toronto Blue Jays, San Francisco Giants, and Detroit Tigers. While these teams vie for Flaherty’s services, the Cubs appear particularly motivated to finalize a deal that could bolster their already formidable roster.
Chicago’s front office, led by Jed Hoyer, has been vocal about its desire to strengthen the rotation this offseason. The Cubs have already made significant moves, including the high-profile acquisition of outfielder Kyle Tucker, signaling their commitment to contention in the National League Central. Adding Flaherty to a rotation that includes Sh ota Imanaga and Justin Steele would provide a significant boost in depth and quality, positioning the Cubs as strong challengers for the division title in 2025. With Flaherty’s familiarity with the NL Central, thanks to his years with the St. Louis Cardinals, and his experience pitching at Wrigley Field—where he has struck out 46 batters in his career—the fit seems almost tailor-made.
Why Flaherty makes sense for Chicago
The Cubs’ recent history has shown an emphasis on pitchers who limit walks and attack the strike zone, and Flaherty’s profile aligns perfectly with that philosophy. In 2024, the Cubs’ pitching staff ranked second in the National League in walk rate, and adding a pitcher like Flaherty, whose walk rate dipped below 6% last season, would further reinforce this strength. Additionally, Flaherty’s postseason experience and proven ability to handle high-pressure situations could be invaluable for a Cubs team aiming to make a deep playoff run.
Moreover, the Cubs are strategically capitalizing on a weakened NL Central landscape. The Milwaukee Brewers, last year’s division winners, are expected to regress following the departures of key players like Willy Adames and Devin Williams. By signing Flaherty, the Cubs would not only enhance their rotation but also position themselves as favorites to capture their first division title since 2020.
A crowded market for Flaherty’s services
Despite Chicago’s strong interest, the Cubs face stiff competition in their pursuit of Flaherty. The San Francisco Giants, Toronto Blue Jays, and Detroit Tigers are all reportedly in the mix, each with their own reasons for pursuing the right-hander. The Blue Jays, for instance, remain aggressive in free agency, while the Giants, under new leadership, are looking to rebound after narrowly missing the playoffs in 2024.
Flaherty’s asking price could be a sticking point for some teams. Reports suggest he is seeking a deal of at least five years and upwards of $100 million, which would place him among the higher-paid pitchers in the league. While the Cubs have shown willingness to invest heavily in talent, it remains to be seen whether they will meet Flaherty’s demands or pivot to alternative options in the market.
What’s next for the Cubs?
If the Cubs manage to secure Jack Flaherty, it would mark a pivotal moment in their offseason strategy and send a clear signal to the rest of the league that they are all-in for 2025. With an already bolstered lineup featuring new addition Kyle Tucker, Flaherty’s presence would round out a pitching staff that combines youth, experience, and high upside. This combination could position the Cubs as legitimate contenders not just in the NL Central but across Major League Baseball.
However, failure to land Flaherty could force the Cubs to explore other avenues, such as pursuing a trade for a top-tier starter or targeting alternative free agents still available in the market. Either way, their aggressive approach reflects a franchise determined to reclaim its place among the league’s elite after several years of rebuilding and retooling.
Broader implications for the MLB landscape
The outcome of the Jack Flaherty sweepstakes will also have ripple effects across the league. If the Cubs secure Flaherty, it could tilt the balance of power in the NL Central, putting added pressure on teams like the Brewers and Cardinals to respond. On the other hand, if Flaherty signs elsewhere—such as with the pitching-hungry Giants or Blue Jays—it could create an even more competitive environment in their respective divisions.
As the offseason progresses, all eyes will remain on Flaherty and the Cubs, who seem poised to make a decisive move. Whether they can navigate the complexities of a competitive market and meet the star pitcher’s lofty asking price remains to be seen. But one thing is clear: the Cubs are determined to make an impact, and Flaherty could be the key piece that helps them unlock their full potential in the 2025 season.
