Since the Chicago Cubs won their last World Series title in 2016, they have reached the postseason just three times. Chicago lost to the Los Angeles Dodgers in the 2017 NLCS, fell to the Colorado Rockies in the 2018 NL Wild Card Game, and was swept by the Miami Marlins in the 2020 NL Wild Card Series.

One factor preventing the Cubs from returning to the top of MLB is their reluctance to spend big on free-agent superstars. Cubs owner Thomas Ricketts addressed the team’s approach in an interview with CNBC, reflecting on the upcoming 2025 MLB season and past regrets. When asked about a major free agent he regrets passing on, Ricketts mentioned Philadelphia Phillies outfielder Bryce Harper, who signed a 13-year, $330 million contract with the Phillies in 2019.

We spent a lot of time thinking about what Bryce Harper is worth as a free agent, sitting with Theo [Epstein] talking about that,” Ricketts told CNBC. “That’s one we kicked around, but obviously, we never executed on. “There were a handful of drafts where you see guys and think, ‘Oh, we could have had this guy, we got this guy.’ But generally speaking, I think our guys have always made pretty good decisions.”

The #Cubs not signing Bryce Harper quite literally marked Tom Ricketts’ heel turn. pic.twitter.com/fKjXONKNlk — Cubbies Crib (@CubbiesCrib) March 21, 2025 The Cubs were not big spenders during the 2018-19 offseason. According to Jon Vankin of Newsweek, the biggest contract the Cubs gave out during that winter was a two-year, $5 million contract to second baseman Daniel Descalso.

Chicago also signed relief pitcher Kendall Graveman to a one-year, $2 million contract and righty Brad Brach to a one-year, $3 million deal. The $10 million in contracts they agreed to with those three players was a far cry from Harper’s deal. Because of that, many journalists, including Jordan Campbell of FanSided, refute the idea that Ricketts had any plans to target Harper to join the Cubs.

“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 is signing the superstar despite the planning that Ricketts said took place,” Campbell wrote Friday on FanSided.

In 2025, the Cubs will attempt to win their first NL Central Division title since 2020. They began the regular season 0-2 after suffering two losses at the hands of the Dodgers at the 2025 MLB Tokyo Series.