Buyer's remorse? Craig Counsell was full of regret after losing NLDS to Brewers

Prior to the 2024 season, former Milwaukee Brewers manager Craig Counsell signed the richest managerial contract in MLB history with their biggest rival, the Chicago Cubs. That alone would've been enough for Brewers fans to hate their homegrown hero for life, but Counsell's betrayal represented an even worse reality. Counsell believed he had a better chance to win long term in Chicago, a front office that was more willing to invest in the on-field product than Milwaukee. He couldn't have envisioned the winning program that was emerging right under his nose.

In the two seasons since Counsell left Milwaukee, the Brewers have won the NL Central. While the Brewers haven't yet broken through to win the World Series – they very well might this year – they've had far more success than the Cubs. Matt Arnold could win his second straight executive of the year award, as well, which speaks volumes about what Counsell left behind. His replacement and good friend Pat Murphy could win NL Manager of the Year as well.

After a demoralizing Game 5 defeat in which the Cubs scratched across just one run, Counsell sounded defeated. We can't blame him in the slightest.

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Craig Counsell came to terms with reality after Cubs NLDS defeat

Counsell was nothing but complimentary of the Brewers following the Cubs Game 5 defeat, seemingly coming to terms with his reality at the same time. Despite leaving Milwaukee two years ago, the Brewers may be better off without him.

“It’s a very good baseball team,” Counsell said of the Brewers. “And a team that deserves and earned their way for the right to go to the World Series. … I’m disappointed. I’m sad. I think this team did a lot to honor the Chicago Cub uniform. In the big picture, that’s how I feel...But, ‘What did we do wrong tonight?’ That’s kind of what you’re stuck on.”

While Counsell spoke more about his own team's struggles instead of the Brewers path forward, as expect, Milwaukee outfielder Christian Yelich did not shy away from the question. Yelich admitted that this series against the Cubs meant a little more than most NLDS matchups.

“This was more than the usual Division Series,” Yelich admitted. “You try to downplay it going into this series against the Cubs and call it any other Division Series, you say you just want to advance. But the rivalry between these two teams – I feel like it’s been our two teams going at it the last eight years – all of the storylines there.”

So, did Craig Counsell make a mistake leaving the Brewers?

I mean, look, it's far too soon to call Counsell's Cubs tenure a failure. He took Chicago back to the postseason for the first time since 2020 this year. Getting back to the playoffs was the goal for the Cubs front office in 2025, and they achieved just that and even won a series over the San Diego Padres. Moving forward, making the postseason ought to be a baseline expectation, rather than the end goal. That was ultimately why Counsell left Milwaukee in the first place. In his mind, there wasn't enough investment to take the Brewers to the next level. Once he left, Arnold's vision came to fruition. Counsell (and most around baseball) did not see that coming.

What makes the Brewers so great as an organization is that they can achieve more with less. It remains to be seen if that somewhat limited investment is enough to defeat the behemoths of the game, like the Los Angeles Dodgers, on a regular basis. We'll find out a lot in the NLCS.

Meanwhile, Counsell's legacy will be defined by his contract with the Cubs. If this team is able to win a World Series in the years to come – likely without Kyle Tucker, I should mention – then Counsell will be able to hold his head high. If not, Counsell's managerial career could go down as a giant 'what if'.