Chicago Cubs manager Joe Maddon is going into the final year of the five-year contract he signed prior to the 2015 season. Despite Maddon's success, that implied uncertainty is going linger at least into next season, at least according to president of baseball operations Theo Epstein: 

And the full context of Epstein's comments: 

Maddon, who turns 65 in February, has managed the Cubs to a 387-261 record (.597) in four seasons. He's made the postseason every year, and in 2016 they of course won the World Series for the first time in more than a century. This past season, however, the Cubs finished second to the underdog Brewers in the NL Central and wound up losing the NL Wild Card Game to the Rockies. Maddon also caused some controversy with the manner in which he responded to the Addison Russell domestic-abuse allegations.  

Ultimately, though, Maddon's fate will likely be decided on the field. According to multiple reports, the Cubs might not be poised to spend much on the free agent market, contrary to longstanding expectations. As such, Maddon could be tasked with going deep into the postseason with basically the same roster. Speaking of which, here's more from Epstein: 

"The group" very likely includes Maddon. Glance at Maddon's overall record, and you'd think a contract extension would be a no-brainer. However, Epstein and Co. appear to want more time to determine whether Maddon is the right manager to lead the organization into the next phase. In that regard, the 2019 standings could be the determining factor.