This team’s free-fall won’t make Tom Ricketts want to spend big money this winter

As the calendar turns to July and all eyes dial in on the July 31 trade deadline, it feels like there are fewer clear-cut sellers than ever, due, largely, to the expanded postseason format MLB instituted in recent years. Facing what essentially amounts to a 'must-win' season, the Chicago Cubs treaded water in June and are already scouring the market for reinforcements.

As 'all-in' as we might hope the Cubs will be, though, don't expect ownership to change its tune on rampant spending suddenly. Really, since just prior to the COVID-19 pandemic, Tom Ricketts has pulled back hard in terms of on-field payroll and, given the team inexplicably went over the first CBT threshold last year, you can safely assume he wants Chicago to dip back under that $241 mark this season.

Seeing high-dollar teams like the New York Mets inexplicably go into utter free-fall in recent weeks won't make him think money is the cure-all, either. Despite carrying the game's largest payroll ($325 million), Steve Cohen's club is just 3-13 in its last 16 games and has fallen behind the Philadelphia Phillies in the NL East race.

Of course, Cohen and the Mets made headlines this winter, signing free agent outfielder Juan Soto to the richest contract in baseball history - a whopping 15-year, $765 million pact that runs through 2039, which will be Soto's age-40 season. Cohen has been as loose as imaginable with his money since buying the team, drawing fire from other owners in the process, but he hasn't yet been able to achieve his ultimate goal: bringing a championship to Queens.

Will Tom Ricketts and the Cubs start acting like a big-market team?

How big market teams spend is constantly a hot-button topic on the North Side of Chicago, with Wrigleyville growing more corporatized by the day and additional revenue streams expanding endlessly. This will be even more the case this winter, when the Cubs will be tasked with locking up superstar outfielder Kyle Tucker long-term.

To do so, Ricketts will have to take the storied franchise into uncharted financial waters. The Cubs have never even doled out a $200 million contract, let alone one in the range Tucker is likely to command: somewhere in the range of $400-500 million. Seeing how the front office and ownership approach the looming trade deadline could offer a glimpse into their thinking heading into a wildly important offseason, as well.