Ross played for the Cubs in 2015 and 2016, serving as a valuable contributor for the 2016 squad that won the World Series, and is now an MLB analyst and broadcaster for ESPN. Although Ross has no major-league coaching experience, he has been mentioned in numerous reports surrounding potential candidates for replacing Maddon, which the press members present at Busch Stadium for the Cubs' season finale versus the St. Louis Cardinals were interested in discussing.

As a result, Cubs starting pitcher Jon Lester and Cubs first baseman Anthony Rizzo, both of whom are close friends with Ross, were asked about the possibility of being managed by their former teammate. While Rizzo described Ross as one of his biggest mentors in the game of baseball, he said that he did not know which direction the Cubs organization was planning to go in.

Rizzo did claim that he felt like Ross managing the Cubs could definitely work out, but he added that he expected the search for the Cubs' new manager to be "a zoo." Lester echoed that sentiment and said that he talks to Ross "as a friend," implying that it would definitely be rather unique if one of his closest former teammates suddenly became his boss.

In a recent radio interview, Ross supported Maddon and opined that the Cubs would be foolish to move on from him. Ross also stated that he was flattered by being mentioned in managing rumors but added that he had not seriously processed getting into coaching in the immediate future. Cubs President of Baseball Operations Theo Epstein told reporters on Sunday that a large-scale managing search will begin once the regular season concludes, so there are certain to be many more candidates added to the fray in the coming days.