And no question looms larger than this: Who will manage the Cubs in 2020?
Joe Maddon's contract will expire at season's end, and the expectation across the MLB landscape is that he won't be retained. Radio.com Sports MLB insider Jon Heyman also sees it that way, saying, "At this point, I think we can all count on the fact that the Cubs will have a different manager next year."
A handful of names have already been connected to the Cubs. That includes David Ross, who serves as a special advisor to Cubs president of baseball operations Theo Epstein, but it's a different individual whom Heyman sees as a front-runner candidate right now: bench coach Mark Loretta.
"At this time it's speculation -- I think Mark Loretta is the most likely candidate to be the Cubs' manager," Heyman said on the Mully & Haugh Show on Monday morning. "He did take a job there coaching, and everyone seems to respect him. His name is coming up with other teams now. Not that that's the reason, but I do think that he will be a very strong candidate to be the manager."
Heyman also explained why he has some doubts about Ross or MLB Network analyst Mark DeRosa becoming the Cubs' next manager.
"I think David Ross or Mark DeRosa would be (leading candidates), but it's not clear at this moment that they're ready or at least in terms of what they want to do that they want to do the job," Heyman said.
The Cubs hired Loretta in January to be their bench coach after he had spent the previous nine seasons working in the Padres' front office.
Several weeks after being hired by the Cubs, Loretta addressed a question about the perception that he was hired as a bench coach to be the Cubs' manager-in-waiting as Maddon worked in his lame-duck season.
"It's not strange because Joe's not making it strange," Loretta said of Maddon's status. "I think he's so sure and confident in his ability that I don't think it's going to be any kind of an issue for him, and I think it will be a trickle-down effect for everybody else.
"I understand the speculation (that Loretta would replace Maddon). Start adding things together, things like that. But Joe is a huge reason why I'm interested in taking this job. I think he's one of the best managers in the game, for sure. One of the best people."