A grin broke across Craig Counsell’s face while putting on his pinstriped Chicago Cubs home jersey for the first time.

“It feels good,” Counsell said Monday at Wrigley Field.

The Counsell era is officially underway for the Cubs, who closed the book on David Ross’ tenure. Ross texted Counsell before the news broke last week of Counsell’s five-year, $40 million deal, prompting Counsell to immediately call Ross.

“I’ve always had great respect for David,” Counsell said. “That gave me the ultimate respect for David the way he handled the conversation. Part of this business is really difficult, it’s really cutthroat. And as a player I’ve lived it, David’s lived it, every player lives it every day. But I respect the heck out of David Ross.”

Cubs Chairman Tom Ricketts spoke to Ross on Nov. 6 after President Jed Hoyer delivered the news at Ross’ home in Tallahassee, Fla.

“These decisions aren’t ever easy or to be taken lightly,” Ricketts told the Tribune on Monday. “But Jed felt like getting Craig in here would get us to the next level, and I support that 100%.”

The focus has fully shifted to 2024 and beyond as Counsell looks to get the Cubs back to the postseason, something they haven’t done over a 162-game schedule since 2018.

“I wanted the challenge of this, all this,” Counsell said Monday. “My hope is the pressure to win in Chicago is just the pressure to win in Chicago. I don’t need any more than that. That’s what it is, that’s what it should be. We should be expected to win.

“It is time to be a Cub. There is momentum happening here and it feels close. And that means there’s a really exciting future ahead of us.”

Here are four things we learned during Counsell’s introduction.

1. Jed Hoyer’s vision for the Cubs’ future sold Counsell.

Counsell said he joked with general manager Carter Hawkins before Monday’s news conference that he doesn’t know much about the Cubs.

The Cubs’ courtship of Counsell lasted less than week from when Hoyer initiated contact Nov. 1, once Counsell became a free agent, to when the Cubs fired Ross and hired the longtime Brewers manager. The fast process prevented Counsell, 53, from delving into studying the organization as he had for the New York Mets opening, for which he interviewed the day after his first conversation with Hoyer.

“I know enough about the city, the franchise, the history and just baseball in general that I know how it works,” Counsell said.

As Hoyer recruited him, he sold Counsell on the health of the organization going forward — specifically the current team, player development and how the front office is built to equip players and provide good information to make the necessary decisions.

“The excitement and where the franchise is at on a big-picture level, we’ve still got to get a lot of decisions right,” Counsell said. “But it’s a really healthy place to start.

“There’s a lot of choices of how to do it, and that’s exciting that there’s several ways to attack the problem. It offers the ability for Jed to be very creative and use any one of those means to do so. In the end, it’s going to be some blend of all that that gets it done. … That gives him a really good chance at being right (and) of this being successful.”

2. Counsell will be deliberate in building his coaching staff.

One of Counsell’s first imprints on the organization will come through the coaches he surrounds himself with.

Now that he’s in place as manager, it leaves the status of Ross’ coaching staff in limbo. While some are expected to remain, how many will return is unknown. There isn’t a specific time frame for when Counsell wants to have his full staff in place.

He plans to be thorough in how he builds the group, and he anticipates it being a slower process. He wants to better understand whom the Cubs have on staff and what they are trying to do with their coaching staff and its infrastructure — including how the current coaches try help players, how the information that is provided helps the players and how that information is delivered. Getting to know the coaches as people is also part of the equation.

All of those facets take time to work through.

“You spend enormous amounts of time with people in close quarters, and so you do get to know people really, really well,” Counsell said. “There’s not many secrets at that point when you’re working that closely with people, and it’s just important to get to know people when you’re working in those situations.

“I want to be deliberate because it’s important and I just need to do more homework is the best way to say it. I hadn’t done homework on the Cubs. I wasn’t prepared (for them to reach out), so it’s a place where I’m behind and I think making a quicker decision is a mistake in this situation.”

The Cubs already had two openings after announcing last month that bullpen coach Chris Young and game strategy and catching coach Craig Driver would not return in 2024.

3. What Counsell’s hiring means to the Cubs’ approach to free agency.

The Cubs possess the financial means to be among the most aggressive teams in free agency and go above the luxury-tax threshold if needed.

Hiring Counsell is a clear sign they are in go mode for their competitive window, though that doesn’t necessarily portend the Cubs signing one of the marquee free agents to a long-term contract this offseason. Hoyer noted last week at the general managers meetings in Arizona that the Cubs are prepared to take a variety of paths to building their 2024 roster, and if they sign or trade for a big name, it would be because things lined up for them.

“Free agency is fun, right? It’s fun to talk about, it’s fun to write about and it’s certainly on the table,” Counsell said. “But the mission for Jed is what’s the best way to build something that can last for a long time. And when I say the organization’s in a healthy place, my perspective of that is he has all those options on the table to do that, but obviously free agency can get you in a lot of trouble.

“There’s certainly the options to do it, there’s the ability to talk about anything. Jed made that clear and that’s exciting, but how you build a team that is going to continually compete, it’s certainly going to take more than free agency and I think we all know that.”

Counsell is considered one of the major leagues’ best managers in part because of how he seemingly always gets the most out of his roster. That did not go unnoticed by the Cubs front office and ownership.

“Obviously he’s had really competitive teams in Milwaukee and done more with what looks like less in terms of on-paper talent,” Ricketts said, “but ultimately also just that steady, consistent, coming-every-night-to-win-the-ballgame kind of attitude that you have to admire about him and we’ve respected about him for many years. And hopefully he brings that kind of attitude to Chicago and gets us to the next level.”

The Cubs roster could use more star talent, especially in the middle of the lineup. Hoyer felt the Cubs left wins on the table this year, and Counsell is expected to mitigate that issue. Infusing the big-league roster with more talent would help too.

“I don’t think it really impacts what we do from a player personnel standpoint,” Ricketts said of the Counsell hire. “Jed would go out and find the best players under any manager. Jed will do what’s right to give us the best chance to win on the field and will let Craig do what he can in the manager’s role to, like I said, get us to the next level.”

4. Counsell underestimated how Brewers fans would take his departure for a rival.

A frosty reception likely awaits Counsell during his first trip back to American Family Field on May 27-30, at least from the Brewers fans among what typically includes a strong Cubs contingent for series in Milwaukee.

Counsell admitted last week was hard, and part of that stemmed from underestimating how Brewers fans would take his leaving his hometown team and the city he called home for 15 of his 25 big-league seasons, including the last nine as Brewers manager.

Pivoting to the division-rival Cubs did not go over smoothly among the Milwaukee faithful, highlighted by a sign being defaced at a Little League field that bears Counsell’s name in suburban Whitefish Bay, where he grew up.

“That was my miscalculation,” Counsell said. “As time moves forward, I’m very proud of what happened in Milwaukee. I think our jobs are to provide a great experience for our fans. I think time will look favorably on what was accomplished during those nine years I was a manager there. It’s there and it’s real and I understand it, too, but I think time will help.”

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When Craig Breslow joined the Chicago Cubs five years ago, he could not have envisioned his path and how his contributions with the organization would play out.

His rise from director of strategic initiatives for baseball operations to assistant general manager and vice president of pitching included meeting with right-hander Jameson Taillon last offseason to recruit the free agent to sign with the Cubs.

“But nonetheless there we found ourselves,” Breslow said this week at the GM meetings in Arizona. “I am grateful for those opportunities, but mostly for kind of that trust.”

The Boston Red Sox hired Breslow, 43, last month as their chief baseball officer. Over the course of the hiring process, he constantly talked to president of baseball operations Jed Hoyer, both to loop him in professionally and take him up on his offer to provide insight and advice during the process. Breslow also spoke with Theo Epstein a handful of times given his success in the same role with the Red Sox.

“I kind of needed to affirm my own beliefs, my own philosophies, my own vision in terms of how to structure and run an organization, so this was an incredible exercise in that,” Breslow said.

Breslow spent five of his 12 big-league seasons with the Red Sox, including winning the 2013 World Series, and his roots remained, living there with his family even while working with the Cubs. He viewed the job as the once-in-a-lifetime opportunity, one he didn’t want to pass up.

“If I had tried to wait until I was absolutely ready to dive in, it may not be there,” Breslow said. “As I’ve gone through the process, I feel both humbled by the expanse of the job but also reassured in that I am ready.”

During Breslow’s time with the Cubs in leading changes to their pitching infrastructure, he witnessed their depth and quality improve, two areas they were committed to strengthening.

“Did we did we get it perfect?” he said. “No, but we set a clear plan and steer in a clear direction and we were able to largely execute.

“I’m not sure how they’re going to replace me,” Breslow quipped. “The organization, is in great hands. … I’m excited to see how that goes from afar.”

The Cubs still are discussing how to fill Breslow’s role, Hoyer said, but they will look outside the organization and also likely promote some people.

“The truth is, honestly, Bres is probably not going to take one person to replace all of the things that he was doing,” Hoyer said, “so we’ll probably look for a multiprong approach to replace him.

“He left us in really good shape. I’m confident that the guys going forward can continue with that infrastructure and do a great job. There’s no doubt he had a big impact on all of our pitching decisions and in that regard he’s always going to be hard to replace.”

The Cubs saw important gains in homegrown arms after Breslow joined the organization in January 2019. Justin Steele’s emergence into a Cy Young Award contender along with the development and matriculation of arms with upside through their minor-league system are part of the dividends from overhauling the organization’s pitching infrastructure. After successfully harnessing ways to increase pitchers’ stuff and velocity, the Cubs must figure out how to improve command and execution system wide. Command training features a lot of uncertainty.

“I told the guys who I left behind that when they figured that out to let me know,” Breslow said, smiling. He expects the Cubs will see that area start to pay off in the next year.

The process wasn’t always smooth, especially at the onset. Although Breslow had total support from Epstein and Hoyer, it was challenging to change the culture, one that had success but hadn’t developed enough pitching. Getting everyone united and moving in the same direction can be difficult given how many people work in a front office and on a coaching staff. Breslow learned from the process and, looking back, might have approached certain things differently.

“But generally the blueprint for success is understand currently where you are, understand where you need to go and understand how you get there and have as many honest, open conversations about that as you possibly can,” Breslow said. “Because at the end of the day, if this is to work, everybody’s going to be perfectly clear on what the pathway was so trying to do anything other than be transparent and candid I don’t think is super effective.”

Hoyer commended Breslow for how he navigated the friction among personnel when it became apparent the Cubs were going to do things differently.

“With any changes, people are going to jump on board and say that’s great, and there’s people that are going to realize this probably isn’t the best place for them and it takes time and change can be hard and he was changing an infrastructure that needed to be changed,” Hoyer said. “He did a great job of that because we needed an overhaul at that point from top to bottom. Our pitching is in a much better place now because he was there.

“You’ve got to build the structures that are kind of anti-fragile and not just like if one person leaves they fall apart, and he hired a lot of really good people and those people step up and do a good job. He was very impactful in building that up.”

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