The Dancing With The Stars runner-up is enjoying retirement, but recently sounded like he would return to the dugout for the "right opportunity." He helped bring a World Series to Chicago in 2016. The biggest hurdle is getting him to leave his family. After that, the biggest issue would be coaching all the players he shared a locker room with.
"“And do I want to put my stamp on a team and the things I believe in? Of course. You see things, even as a casual fan, you start to want to kinda do things your way.” “It’s all about opportunity. I think when you have to give up and sacrifice family time, it’s gotta be worth it. I don’t do things halfway, I go all-in, so that’s a huge commitment from me.”"- David Ross
Joe Maddon's bench coach is the heir apparent and the most-likely internal candidate. Loretta spent nine years as a special assistant with the San Diego Padres before coming to Chicago in January. One year in the dugout and you qualify to be in charge of a perennial playoff-contender. Really makes you wonder how hard it is to be a manager.
The biggest-name option for the Cubs and the only guy with any experience. Girardi won 103 games and a World Series with the New York Yankees in 2009. He was replaced by Aaron Boone after the 2017 season. He's been rumored as a potential replacement since it was revealed that he was holding out for a dream job. Managing the Cubs, who are a year-removed from four straight postseason appearances, would probably qualify.