Chicago Cubs Rumors: Could Theo Epstein reunite with Maddon?

Chicago Cubs President Theo Epstein could be leaving the organization soon. Could he reunite with Joe Maddon and the Angels in Anaheim?

According to David Kaplan of NBC Sports Chicago, Chicago Cubs President of Baseball Operations Theo Epstein is meeting with owner Tom Ricketts to discuss his future with the team and impending exit from the organization.

While it’s a near certainty that Epstein will not be signing an extension after his contract is up in 2021, it’s also possible that Epstein departs during the current offseason and heads to his next project to build a World Series contender.

While there will be no shortage of options for Epstein, his track record has largely revolved around building a championship contender from the ground up.

There’s many teams in baseball who could use a Theo Epstein, such as the Cincinnati Reds or New York Mets. Both teams missed the playoffs in 2020 and are ranked in the bottom 2/3 of farm system rankings.

Epstein’s model of a total rebuild could be just the fit for either organization.

On the other hand, perhaps Theo would like to go to a team who already has a respectable base of players and expand his reputation to include a model other than just building from the ground up and taking years to become a contender.

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Take the Los Angeles Angels for example.

The Angels are already equipped with the best player in Major League Baseball and one of the top five third basemen in the game, as well as one of the top prospects in baseball.

They also have a proven manager in former Cubs manager Joe Maddon, currently third in all-time wins of active managers. Maddon and Epstein, of course, were together in Chicago from 2015-2019 and won the 2016 World Series.

Oh, and there’s also the fact that the Angels are in the midst of a search for their next front office leader after firing former GM Billy Eppler last week.

According to MLB Trade Rumors, the Angels are looking to make a hire by the end of November and aren’t just limiting themselves to a GM but could also look to hire a new President of Baseball Operations.

When Maddon’s contract expired after the 2019 season, it seemed as if it was a mutual decision on both sides to not renew the World Series champion skipper’s contract.

Not long after the divorce, Maddon and Epstein opened up to ESPN about their differences in management styles with Maddon confessing that he preferred to “let the boys play” and Epstein seemingly wanting to make some changes and be a bit more hands on.

While this could be a deterrent in Epstein heading to Anaheim, it also could be the perfect marriage.

It’s clear that Theo doesn’t like to stay at the same place after the job is done and the club has won a championship. That’s what he does. He makes team relevant and wins a World Series, then heads to his next project. It’s what he did in Boston and seems to be how it will end in Chicago.

But perhaps that’s exactly what all three parties need. Theo to bring in the personnel, Maddon to steer the ship to the title and everyone to go on their happy way after a title.

After all, Maddon will be 67 years old at the start of the 2021 baseball season and likely won’t be managing much longer after his tenure in Anaheim.

It works out well for everyone. Theo and Maddon get another notch in their belt while potentially guiding the best player in baseball and a team that has only won one World Series to another title.

They would certainly need to compromise on their differences and Epstein would have to adapt to a new model of rebuilding, which could be exactly why he doesn’t even consider it. But it also would further expand his reputation and success. Think of it as Theo going from just a “new build contractor” to “remodeler.”

It’s certainly not outside the realm of possibilities, and Epstein has spent a good amount of time in Southern California while getting his JD at the University of San Diego and during his tenure with the San Diego Padres.

And admittedly, this may all for nothing if Epstein remains with the club through 2021 and the Angels hire someone else.

But in the event that Epstein does leave this season, it’s certainly something that could make sense. That is, if all parties think it makes sense

Until then, all we can do is speculate.