If the Chicago Cubs keep winning, will the front office still sell?

I was texting with my brother-in-law on Thursday about the state of the Chicago Cubs. Admittedly, we have very different thoughts about this team and the direction that should be taken at the trade deadline.

He’s of the mindset that the last three weeks are more indicative of what this roster is capable of than what we saw early on in the year when the bats looked lost and the rotation was mired in deep, deep struggles. Meanwhile, I think that, unless Jed Hoyer is confident he’ll be able to get an extension done with at least one of the team’s ‘big three’, he needs to be a seller this summer.

The Chicago Cubs owe it to the fans to act like a big market organization

To be clear, the Cubs don’t have to sell. They don’t need to re-tool or rebuild. What they need to do is get back to acting like a big market team and put their tremendous resources to work in getting the team back to the World Series. But I also have serious doubts the Ricketts family will do so, instead leaning on their oft-repeated excuse of major losses in the wake of the pandemic-shortened and fan-less 2020 campaign.

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Kris Bryant has emphatically shown he’s far from done and is still more than capable of anchoring a lineup with an MVP-caliber performance. That also means his trade value will never be higher than it is right now. For Hoyer, that offers an opportunity to flip the superstar for a return that could pay dividends for years to come.

But if he does that – and the Chicago Cubs are still in contention – he’ll immediately join Tom Ricketts in the circle of unpopularity that’s developed in recent years. The same can be said for trades of Javier Baez, who pulled off perhaps his most unbelievable play yet on Thursday against the Pirates, and Anthony Rizzo, who is battling lingering back issues of late.

The team’s bullpen, which is in the midst of the longest scoreless inning streak in franchise history, has been led by veteran Craig Kimbrel in the ninth inning. The future Hall of Famer has returned to form in a big way with 11 saves, a 0.86 ERA and an impressive 15 K/9 mark.

He’s one guy that, at least in my mind, Hoyer has to trade this summer – and sooner, rather than later. There are plenty of teams that could use an elite late-inning arm and given he’s heading into the back half of his 30s, there is little doubt that Kimbrel’s best days are behind him. Not trading him just in hopes of sneaking into the postseason one last time just doesn’t make sense.

Chicago has just over $70 million on the books for 2022 – a good chunk of which is tied up in Jason Heyward ($24.5 million). For a team with the financial resources the Cubs do, there’s zero reason that, even if the team sells hard this summer, they don’t become major players in this winter’s loaded free agent class.

Last offseason, the Yu Darvish trade sent a resounding message to the team and its fans: we’re focused on the future. Apparently, though, the players don’t care about that message – and they’re here to do what they can to make Hoyer’s job in the coming months as difficult as possible.