If the Cubs do sell, when can we realistically expect them to be good again?

2024 was supposed to mark the end of Chicago's rebuild - but it's clear there's still a lot of work to be done.
Chicago Cubs v Milwaukee Brewers
Chicago Cubs v Milwaukee Brewers / Stacy Revere/GettyImages

Last summer, when the Chicago Cubs came up one game shy of their first full-season postseason appearance since 2018, with some time, most of us were able to remind ourselves that the team's surprise second-half run was really a year ahead of schedule.

2024, after all, has been the year circled on the calendar since Jed Hoyer started tearing things down with the Yu Darvish trade in late 2020. Of course, the 2021 trade deadline is what stands out when we look back, as an emotional fanbase watched Kris Bryant, Javier Baez and Kris Bryant get traded in a matter of days.

But here we are, more than halfway through the 2024 season and all the Cubs have to show for their efforts are an 11 1/2 game deficit in the NL Central and a 39-46 record. The salt in the wound is the team running away with the division, the Milwaukee Brewers, are coming off an offseason in which they traded a former Cy Young winner in Corbin Burnes and watched their longtime manager join their most hated rival in Chicago.

"I think that when you look at the way we performed this year with a team that’s stronger, it’s less. And is that frustrating to me? Absolutely. And if it’s frustrating to me, I have to imagine it’s frustrating to the fans. So yeah, I think that it is something that I completely empathize with."

Jed Hoyer, via Marquee Network

That hasn't slowed the Brewers at all, with Pat Murphy looking like a strong Manager of the Year candidate in his first season at the helm. Meanwhile, Counsell's Cubs have looked listless for two months and now face a prospect that felt unthinkable this spring: selling at the trade deadline for the third time in the last four years.

Cubs keep spinning their wheels, hoping to again be a contender

Chicago had a chance to get back on track in its last 25 games before this weekend's disappointing showing in Milwaukee, with a soft schedule littered with sub-.500 teams. Instead of turning the corner, though, the Cubs went 10-15, continuing their free-fall.

The problem with the Cubs being sellers is a lack of clear trade chips. With how the roster is constructed, selling will likely mean moving guys with multiple years of control remaining like Nico Hoerner or Ian Happ. Guys like Mike Tauchman or Kyle Hendricks aren't going to get you anything of value on their own, so Jed Hoyer could be forced to move guys we might not expect.

If that's the path the Cubs take, the timeline for returning to contention could be stretched out even further - especially if ownership continues to force the front office to sit on the sidelines on the top end of the free agent market. After years of re-tooling and re-loading, the quality of the big league team is leaps and bounds from where it needs to be - and there's no clear path out of this mess, at least not without a dramatic shift in thinking from Hoyer and his team.