ESPN dares Cubs to fix the one problem fans won’t stop talking about

Each offseason, it seems that the Chicago Cubs are challenged to act like the big-market team that they are and spend heavily in free agency. Since the Cubs won the World Series in 2016, the front office hasn't had the same urgency in the offseason. The stage is set for them to do so this offseason, having already had a season of Kyle Tucker on their roster, but many feel talking about it is already a lost cause.

In making a prediction for the Cubs' offseason, ESPN's Bradford Doolittle all but challenges the team to do the one thing they have willingly shied away from. Doolittle believes that Tucker will get the lucrative long-term deal this offseason, but it won't be with the Cubs.

"Call me a pessimist, and this is more of a hunch than anything. Financially, the Cubs should be in position in terms of revenue profile and payroll outlook to get a deal done. But until they prove otherwise, the Cubs have a track record of not going all the way to the top in free agency.," Doolittle wrote.

Cubs challenged by ESPN to stop playing scared and take the leap

The issue is that the Cubs have routinely kicked the can when it comes to spending aggressively during the offseason. After the sell-off at the MLB trade deadline in 2021, the expectation was that the Cubs would return to spending like a big-market team once they were ready to return to contention. In theory, the Cubs' contention window has been open for the last three years, and their payroll has gone down rather than up. The Cubs have had money to spend, but with Hoyer set on finding the right value in any deal he makes, there are opportunities left on the table.

With Hoyer signed to a multi-year extension, the idea of the Cubs returning to being an aggressive spender in the offseason should be discarded. That isn't how the Cubs have done business in a long time, and it's hard to imagine that will change anytime soon.