Now is Not the Time for Contract Talks with Joe Maddon, But When Is?

Since joining the Chicago Cubs back in the fall of 2014, Manager Joe Maddon has steered his team to 360 wins and 245 losses over three and a half seasons. Oh, there’s also the three straight NLCS’s, two NL Central titles, and a World Series trophy on the shelf, but who’s counting?

Indeed, even if you’ve never been keen to Maddon’s style, there’s really no denying the success the team has had while he’s been at the helm of the Chicago Cubs.

But how long will he be there?

If you recall, Maddon’s original five-year/$25M deal with the Cubs extends through next season, before finally expiring (thanks to some performance bonuses, the deal has since been something closer to 5 years, $28M). And he also happens to be the oldest active manager in baseball. So the questions of if the Cubs are going to extend him anytime soon, and whether they should, are rapidly approaching a time for deciding.

On the latter question, there’s really no question at all in my mind. Joe Maddon has had a TON of success in Chicago, the players love him, the front office loves him, he’s had a ton of success in Chicago, he actively blends modern analytics with an old school mentality, he’s had a ton of success in Chicago, and, of course, he’s had a ton of success in Chicago. If Maddon wants to stay on for a while longer, I don’t see a reason why the Cubs would not be on board.

But have the Cubs begun considering it? According to Theo Epstein, not quite yet: “Nothing like that is even a thought in our mind right now,” Epstein said yesterday. “Probably not in Joe’s (mind), either. We’re just focused on trying to make the absolute most of the season.” He continued: “I’d say the appropriate time for us, internally, is to start thinking about it after we play our last game.”

Got it, so the Cubs will start thinking about a Joe Maddon extension after Game 4 of the 2018 World Series (#CubsInFour).

Jokes aside, I do think the Cubs and Joe Maddon will ultimately come together on an extension of some form, because I believe the front office when they compliment him on the work he’s done this season, despite obvious hurdles: “He’s done the same great job that he’s done since he’s been here,” Epstein said. “We’ve got a deep roster, and he’s managed to use the whole thing and keep guys in spots where they can succeed. He’s been real steady. You can’t tell with him whether we’re on a hot streak or whether we’re struggling. He creates an environment that gives guys a lot of freedom and allows them to sort of be themselves and thrive.”

There are many more quotes from Joe Maddon, Theo Epstein, and some of the players (Jason Heyward, David Bote, etc.) on the matter at The Athletic, if you’re interested. 

As for running this thing down to the wire, well, that’s not all that uncommon for this front office/team. If you recall, Theo Epstein’s own extension ran way down to the wire, waiting until September of his own five-year contract with the Cubs before working out an extension. Perhaps that was different given his position in the organization, but maybe there was a lesson to learn there. Maybe, when you’re working in good faith with a group (Tom Ricketts, Epstein, Maddon) that all really wants the same thing, you just don’t worry about timing.

In the end, if 2019 is going to be Joe Maddon’s last year as the Cubs’ skipper, I think it’ll be because he retired and not because the Cubs don’t extend him. But I think it’s more likely that he’s extended, and that probably comes this offseason.

If you’re thinking about how long the extension will be, keep in mind that the front office and many of the Cubs’ core players are all under control through 2021.

written by

Michael Cerami began covering the Chicago Cubs for Bleacher Nation as a part-time contributor in 2015. One year later, he joined Bleacher Nation full-time, covering the Chicago Cubs and Major League Baseball. Today, Michael runs Bleacher Nation, contributing as a writer (Cubs, MLB) and an editor for all sections of the site, including the Chicago Bears, Bulls, and Blackhawks, as well as MLB, NBA, NHL, and NFL. In 2019, Michael was the co-host of NBC Sports Chicago's Cubs Post-Game Show Outside the Ivy. You can find him on Twitter/X @Michael_Cerami

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