President of baseball operations Theo Epstein thinks everything is going to work out just fine.
"My bet is that it goes extraordinarily well with Joe and the whole group and that he's here for a long time to come," Epstein said.
Maddon, who turns 65 next month, is under contract for one more year after Epstein and the Cubs decided against offering him an extension over the winter. They want to see how the team rebounds from a disappointing finish last year.
Chicago posted at least 92 wins and made the playoffs in each of Maddon's first four seasons as manager. It won the World Series in 2016 for its first championship since 1908.
But the Cubs blew a five-game lead in the NL Central last September. They lost to Milwaukee in a tiebreaker for the division title and then dropped the NL wild-card game against Colorado.
Cracks in the relationship between Maddon and the front office seemed to develop during the season. But on Saturday, there was nothing but praise from Epstein.
He credited Maddon's handling of the young players in 2015 and 2016 for that drought-busting title. He praised Maddon's ability to create an environment that allowed them "to have fun." He also mentioned Maddon's flexibility and willingness to adapt.
"The great thing about Joe is even though he's a little bit older than me, he's never standing still," Epstein said. "He's never satisfied. He's a creative person. I think he's an adaptable person. He's someone who likes the challenge. He is someone who is going to bring great energy to solving any problem."
One big challenge for Chicago: Getting more out of an inconsistent lineup.
Sluggers Bryce Harper and Manny Machado remain free agents, but it doesn't sound as if Epstein has room to fit another blockbuster contract into his budget for next season. A healthy Kris Bryant should help, after a left shoulder injury limited the 2016 NL MVP to a career-low 102 games.
If the Cubs get more at the plate from Willson Contreras among others, they believe they can eliminate the wild scoring swings that hurt them last season. Chicago was fourth in the NL in runs but had one or zero in 39 regular-season games.
"We felt like we should have hit better than we did," Ben Zobrist said. "Changes were made. Some structural changes are being made as well at the same time, the way that we're gonna go about some of the routines and things like that. That's the challenge that we have ahead of us as a hitting group, knowing how we're gonna handle those dips in those times where things don't go as well."
Chicago has a new hitting coach, with Anthony Iapoce replacing the fired Chili Davis. Iapoce held a similar job with the Texas Rangers the past three seasons. He was a special assistant in the Cubs' front office from 2013-15, overseeing their minor league hitting program and working with several of their current position players.
"He's great," Bryant said. "He's really good. When I worked with him, it wasn't necessarily mechanics. It was more the mental side. I think we all have the talent to be a good hitter or we all wouldn't be here."
Epstein is banking on the Cubs rebounding, delivering more consistently at the plate. If they do, that could go a long way toward determining whether Maddon remains their manager.
"It hasn't fully happened the way we expected it to," Epstein said. "I don't think this offense is fully realized. ... I think you're going to see significant bounce-back."