One night during the 2020 season, Chicago Cubs veteran outfielder Jason Heyward took catcher Willson Contreras out to dinner.

Teammates having dinner together isn’t atypical, but on this occasion it served a specific purpose. Heyward knows better than most the highs and lows within a season and career. Heyward’s advice centered on the big picture: Communicate when you might need help. If something isn’t going your way, take your time. Observe and learn.

“His job has a lot of expectations, so I wanted to acknowledge that I understand it’s not easy as a catcher coming in at the time he came into this organization and let him know I was there,” Heyward told the Tribune. “I understand what he’s trying to do is hard and what he wants to accomplish, letting him know that, over time, most likely there’s going to be coaches that come and go, that’s just a part of the game — different systems, different mindsets — but that he’s going to be here a lot longer than a lot of people.”

When Contreras arrived at big-league camp in March, a lot of questions focused on his impending free-agent status. Six minutes into his first media availability, the topic of leadership came up. Contreras, one of the more veteran Cubs players, cited the importance of knowing when to speak up and be vocal.

He has become a leader on the new-look Cubs.

“The right time is this year because we have really good young players that might need help, might need advice, might need a hug, whatever,” Contreras told the Tribune. “I want to be available for them and be the best I can be out there.”

Contreras’ path to becoming a more noticeable leader is a product of a deliberate investment by the 29-year-old catcher over the last few years. The work he has put into that area has not gone unnoticed by Heyward and Kyle Hendricks, the only two teammates remaining from Contreras’ 2016 rookie season.

“It’s his time,” Heyward said. “This is the way the game goes. At a certain age and certain time, things are one way with teammates, coaching staff, whatever. And now a lot of those guys are gone for us. Now Willson has an opportunity to see more things coming. … A lot more guys are going off of you, and I think he understands that and appreciates it. He doesn’t take that lightly.”

Before the Cubs dismantled the roster at last year’s trade deadline, Contreras felt his place was to shut up and listen. He admitted it took a while to accept all the trades, believing they were a playoff team all the way up to the deadline. The changes ultimately created an opportunity for Contreras to become a more vocal presence.

Now, Contreras possesses a coveted perspective, and as a catcher it can carry extra weight because of how he is involved in all parts of the game.

“If you want to be a leader, you have to respect everyone, every teammate,” Contreras said. “If you want to be a leader, you have to get to the ballpark on time. You have to show them how you go about your business and not show up an hour or two before the game. I think that’s how you gain respect from teammates and respect for the job.

“Holding everybody accountable when they do something wrong, doing it the right way. Don’t show up someone in front of everybody.”

After Contreras earned his big-league call up on June 17, 2016, he was a constant source of energy. His vibe was a welcome addition to the eventual World Series champs.

But over the course of those final four months of the season, Hendricks saw Contreras come to understand that maintaining his level of energy for a full 162-game slate at a demanding position would be challenging.

Now in his seventh big-league season, Contreras’ knowledge of his body and how to manage the long year also plays a role in the evolution of his leadership.

“He’s realized where to pick his spots,” Hendricks told the Tribune. “Willson has grown into himself in the way that he’s just confident and comfortable in who he is, as a player and a person. He’s settled into himself.

“He knows when is the right time to say something and when is not just based on experience.”

Hendricks thought Contreras did a great job last season handling the Cubs’ less experienced pitchers, specifically with how to support them in various game situations. He recalled watching Contreras come into the dugout after innings knowing when was the right time to approach and go over something versus letting a younger pitcher work through a learning experience on their own.

“He really was able to identify those situations with the young guys and really feed into that and make them feel comfortable or pump them up, whatever they needed in that moment,” Hendricks said.

Contreras appreciates how Hendricks and Heyward recognize his efforts to be a better leader and player.

“The way you prepare shows everyone you care,” Contreras said. “If I was the type of guy that just shows up late and just gets ready for a game, nobody will respect me. Or if I don’t play the game the right way or don’t hustle.”

The departures of Anthony Rizzo, who spent a decade in a Cubs uniform, Kris Bryant and Javier Báez appeared to deal a blow to the clubhouse beyond their on-field capabilities.

Asked if he agreed with the perception the Cubs lost leadership after last year’s trades, Heyward said his answer might not be popular.

From his perspective, those views are from fans and media who don’t have insight of what’s happening in the clubhouse. Heyward acknowledged players don’t possess control over everything because of the business side to the game, especially when dealing with contract uncertainty.

“Anytime you have a natural built-in distraction, it does make things a little bit harder and does take the focus off of just going out and playing the game,” Heyward said. “I saw that with our group last year. And that’s not a knock or excuse, that was our reality last year. As far as what didn’t come back through the door this year, it was just time for change. That’s what came about.”

Heyward appreciates the Cubs’ offseason acquisitions featured a lot of players who have a different perspective of winning at the major-league level. Among them: infielder Jonathan Villar, catcher Yan Gomes and pitchers Marcus Stroman, David Robertson, Drew Smyly and Chris Martin have combined to be part of 49 postseason series, six World Series and four titles.

The roster overhaul doesn’t diminish the Cubs’ special six-year span preceding the trades. Heyward anticipates fans being surprised by the Cubs this season, even if their style of play looks different than the past few years. He views the changes as good organizationally and for what comes next.

“I do love the fact that we don’t have to show up every day and chase results,” Heyward said. “I think that’s a trap. The things we try to pay attention to detail on, things we want to focus on that are very important in the game, I think we’re going to see a lot of success and have a lot of fun playing.

“Everyone’s focused in the moment, no one’s really looking at, ‘Oh, what about a contract? Where am I going to be?’ All those things are very tough and a part of the game,” Heyward said. “But now Willson can be here, and guys will appreciate a lot about him being in that space.”

Contreras might be the next star to leave the Cubs, whether that decision is made by him or the franchise. Over the last seven weeks, the unclear future hasn’t affected Contreras’ responsibilities or his investment as a leader.

“This energy is there,” Contreras said. “Players are willing to listen, they’re willing to make sacrifices to win games. We’re sticking together.”

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