Tom Ricketts has had the unfortunate trend of every time he says something about where things stand with the Chicago Cubs and their payroll, he winds up putting his foot in his mouth.
There have been several instances this offseason where Ricketts has all but confirmed that as long as he is the team's chairman, there shouldn't be an expectation that the Cubs will be at the top of the market in terms of free-agent spending.
On the surface, that's a realization that Cubs fans should have had following the 2018 season. The 2018 season marked Bryce Harper's last season with the Washington Nationals before reaching free agency. For a Cubs' team that has been unceremoniously bounced from the 2017 NLCS, the impression was that the front office was eyeing Harper to be their next superstar. The Cubs keeping their contention window open with Harper's arrival seemed inevitable just until the end of the 2018 season was reached.
The end of the 2018 season marked a shift in the dynamic between Ricketts and then-President of Baseball Operations Theo Epstein. Epstein relied on spending in free agency to overcome organizational deficiencies. no longer had Ricketts' open wallet at his disposal. In fact, Epstein barely had any money to make use of as adding utility infielder Daniel Descalso on a two-year deal was the only move of significance made that offseason.
Meanwhile, Harper inked a 13-year deal with the Philadelphia Phillies for $330MM. The rest, as they say, is history.
Making things even more irritating, during a recent interview with CNBC, Ricketts expressed some regret over the Cubs not making the move for the Harper.
The #Cubs not signing Bryce Harper quite literally marked Tom Ricketts’ heel turn.
— Cubbies Crib (@CubbiesCrib) March 21, 2025
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Tom Ricketts' regret over not adding Bryce Harper feels like an insult to Cubs fans
In order to have regret, you have to have a seat at the table. Given the Cubs spending the offseason Harper was a free agent, and their spending habits since, it's very clear the team never had any real interest in signing the superstar despite the planning that Ricketts said took place.
Also, if that regret were real, you would think think that Ricketts would be sure to avoid a similar mistake with Shohei Ohtani and Juan Soto. Instead, the Cubs were never considered a serious suitor for Ohtani and last offseason, the team went out of their way to confirm they had no interest in signing Soto.