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Chicago Cubs: Joe Maddon, 2015-Present
In the modern-day age of baseball, there may be no better manager in the game than Joe Maddon. It could be argued that Maddon is the most excellent manager the Cubs have ever had to lead their franchise.
A disastrous 2014 season saw Chicago finish last in the National League Central division with a 73-89 record. Bucking previous trends of managerial musical chairs, Epstein brought Maddon in to lead the charge. In his first season, the team finished 97-65, finishing as the Wild Card team and making it to the National League Championship Series.
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The next year was historic for Maddon and the Cubs. During a press conference with Javier Baez in January of 2016 at Cubs Convention, Baez was asked the advice Maddon had given him when he made his major league debut. Baez responded with the infamous four-word answer, “Try not to suck.”
It was a mantra which helped motivate the Cubs to a 103-win season and their first world championship in 108 years. The 2017 season was another solid season for Maddon, as he led the team to a third straight NLCS appearance and a 92-win season. Last year, the club finished 95-68, losing in the Wild Card Playoff to the Colorado Rockies.
So far this year as we head into the final weeks of the season, the Cubs sit at 82-68, two back of first behind the St. Louis Cardinals and leading the Wild Card race for the second spot. If Maddon can lead the team to the playoffs, they will have reached the postseason in each of Maddon’s first five seasons in Chicago.
Maddon has a career 469-329 record with the Cubs, suitable for a .588 win percentage. During that span, the club has won the division twice, has made three straight NLCS appearances, have won a pennant and, of course, a World Series title. Needless to say, Maddon could rank as the best manager in Cubs history and its not particularly close.