SCOTTSDALE, Ariz. — As the calendar turned from October to November, Cubs president of baseball operations Jed Hoyer looked at a particular free agent with piqued, yet reserved, interest: Craig Counsell.

The former Brewers manager had his contract expire on October 31, meaning he was free to talk with any team without requiring permission from Milwaukee. As October neared an end and Counsell remained in limbo, Hoyer contemplated the idea of reaching out.

On the one hand, he had a manager in David Ross who he and the whole organization had total confidence in. On the other was arguably one of – if not the best – managers in baseball right now.

So, he remembered his role and removed any biases he may have had in his friendship with Ross.

“I feel like I have a responsibility to the city, to the fanbase to winning as many games short-term and long-term as I can and this felt like it checked that box,” Hoyer said in a 30-minute conversation with media at the Omni Resort where this year’s GM Meetings are taking place. “It was a really hard decision and obviously some very hard conversations that went in with that, but I felt like it was just the right thing to do.”

Hoyer kept his plan close to the vest — if the interest leaked and Counsell didn’t wind up in Chicago, it would put him and Ross in an unbelievably awkward situation. He informed Cubs chairman Tom Ricketts of the interest and not too many others.

“My circle was literally as small as you could make it just in thinking about it,” Hoyer admitted.

Hoyer and Counsell met in person last week. The pair hadn’t had too much interaction in the past, limited to some conversations nearly a decade ago when Counsell was a special assistant to the GM in Milwaukee.

“Because we’re rivals, so to speak, there’s not much congeniality,” Hoyer admitted.

Hoyer came away from the meeting impressed. He learned more about how Counsell operates as a manager and Hoyer pitched to Counsell on the organization and what their vision for the team was going forward.

“This guy wants to handle every single part of the process and views that as his responsibility and to me that’s really impressive the way he views his chair so much more than making a bunch of in-game moves,” Hoyer said. “He views the totality of everything as his responsibility and talked about that in an amazingly articulate way.”

That’s not to say that wasn’t something Ross did or didn’t do. But, in Hoyer’s opinion, Counsell shone around the edges so much more that it was hard not to want to target him.

The Cubs in 2023 outperformed external expectations, without a doubt, but there was still a sense of emptiness that reverberated around the organization. They had a 92% chance of reaching the playoffs early in September, only to miss out on the postseason by a game. Hoyer and the Cubs felt that they “left wins on the table” which contributed to that hollow feeling.

In bringing Counsell aboard, Hoyer and the Cubs hope that there’ll be fewer of those wins left on the cutting board. Counsell’s track record in Milwaukee certainly showed that — and Hoyer had a firsthand look in 2017.

The Brewers that year, led by Counsell, were an upstart team, pushing the defending champion Cubs in September and ensuring there was a fight in the Central.

“That team had no right to be there,” Hoyer said of the 2017 Brewers. “They made us play to the last week of the season, but from a talent standpoint, that wasn’t close. That was probably the time where [we were like] ‘What are they doing?’”

That jumpstarted one of the most successful runs in Brewers’ history. In 2018, Milwaukee won the division and they fell in Game 7 to the Dodgers in the NLCS. The Brewers won the division 3 times since 2018 and made the postseason 5 times in that span.

“Consistently, year after year after year, they’ve outperformed expectations, which is really impressive,” Hoyer said.

Now, the hope is that sort of success can follow Counsell 90 miles south to Wrigley Field. 

Hoyer banked on that. And he did it because he felt and knew it was the best thing for the franchise — just like the multitude of difficult decisions he’s made since he was elevated to head of baseball operations in 2020.

“I have had to make a lot of those decisions and ultimately what I always try to get to a point of is [if] it’s a really hard decision and I’m willing to make it, then I feel like that means that I’m doing the right thing for the organization,” Hoyer said. “Yes, it was incredibly hard to let Rossy go. I felt like it was my responsibility to the organization to do that. That’s why I can sit here and say, yeah, I think Rossy’s a very capable manager and has a really bright future.

“I thought the best thing for this fanbase was the move that I made. It was really hard. But I think that’s why Tom hired me.”