Maddon, who led the team to four consecutive playoff appearances and the 2016 World Series championship, went into the 2019 in the final season of a five-year contract, and after Sunday's game he could become the most sought-after managerial free agent this offseason.
"We both agreed that it's time, and this type of change is necessary," Cubs President of Baseball Operations Theo Epstein said.
Epstein and Maddon met in a St. Louis hotel room on Saturday night to discuss the path forward for the team and celebrated one of the most successful five-year runs in the team's history.
"I'm really excited about the future. I'm excited about the Cubs' future," Maddon said.
Maddon told reporters prior to Sunday's game against the Cardinals that he had gathered the team at their hotel on Friday to inform them that he would not be coming back for the 2020 season.
The Cubs hired Maddon after the 2014 season, firing then-manager Rick Renteria in favor of Maddon after he exercised an opt-out clause in his contract with the Tampa Bay Rays.
The move paid immediate dividends for the Cubs, as they reached the postseason for the first time in seven seasons and made it to the National League Championship Series after beating the Pittsburgh Pirates in the National League Wild Card Game and the St. Louis Cardinals in the Division Series.
Maddon captured National League Manager of the Year honors thanks to the Cubs’ turnaround, and Kris Bryant won Rookie of the Year honors for his stellar first season. Jake Arrieta also won the Cy Young Award after a sterling second half performance.
In 2016 the Cubs fulfilled the dreams of generations of fans, capturing their first World Series championship since 1908 by beating the Cleveland Indians in seven games. The Cubs erased a 3-1 series deficit to capture the title, the first of Maddon’s managerial career.
The Cubs reached the National League Championship Series for the third straight year in 2017, but were dispatched in five games by the Los Angeles Dodgers. The team made some changes to its coaching staff, including parting ways with Chris Bosio, but opted to retain Maddon for the 2018 season.
That season did end with a fourth straight playoff appearance, but after losing a divisional tiebreaker game against the Milwaukee Brewers and the wild card game to the Colorado Rockies, the Cubs allowed Maddon to enter the 2019 season as a lame duck manager in the final year of his contract.
The 2019 campaign started out rough with the Cubs getting out to a 1-7 start, but the team looked poised to make a fifth straight playoff appearance as September began. A late collapse, including a four-game sweep at the hands of the Cardinals at Wrigley Field, put a huge dent in the team’s postseason chances, and they were officially eliminated in the final week of the regular season.
Now the team will focus on trying to find a new manager, with former catcher David Ross, former second baseman Mark DeRosa, current bench coach Mark Loretta, and first base coach Will Venable all listed among potential candidates by various national baseball reporters.