After co-managing with Silver Flint during the 1879 Chicago White Stockings season, Hall of Famer Cap Anson began an 18-year managerial tenure in 1880, the longest in franchise history. Under Anson, the team won five more NL pennants — in 1880, 1881, 1882, 1885 and 1886—tying the 1885 World Series and losing the 1886 World Series in the process.[a] Anson won 1,283 games as the White Stockings' manager, the most in franchise history. After taking over for Hall of Fame manager Frank Selee in 1905, Frank Chance — another Hall of Famer — managed the team through the 1912 season. During his tenure, the franchise won four more NL pennants in 1906, 1907, 1908, and 1910, winning its only two World Series titles in 1907 and 1908. Chance's .664 career winning percentage is the highest of any Cubs manager. After Chance, from 1913 through 1960, the Cubs employed nineteen managers, nine of which were inducted into the Hall of Fame. During this period, the Cubs won six more NL pennants, including three under manager Charlie Grimm. Split between Grimm's two managerial stints in the 1930s and 40s, plus a brief appearance as manager in 1960, Grimm accumulated 946 career wins, second-most in franchise history behind Anson.
Owner P. K. Wrigley then began experimenting with the managerial position and in December 1960, announced that Cubs would not have only one manager for the coming season. Instead, the team implemented a new managerial system known as the "College of Coaches". The system was meant to blend ideas from several individuals instead of relying on one manager. During its first year, the team rotated four different managers into the role: Vedie Himsl, Harry Craft, El Tappe and Lou Klein. The next year, under the guidance of Tappe, Klein and Charlie Metro, the Cubs lost a franchise-record 103 games.Bob Kennedy managed the team for the next three seasons until Hall of Famer Leo Durocher assumed the managerial role for the 1966 season, effectively ending the five-year-long "College of Coaches" experiment. During his first season as manager, Durocher's Cubs tied the franchise's 103-game loss record set four years earlier by the "College"; however, he maintained a winning record for the rest of his seven-year tenure.
In the last 37 seasons since Durocher, the Cubs have had 22 managers. Jim Frey and Don Zimmer led the team to the National League Championship Series (NLCS) in 1984 and 1989, respectively. In both of those seasons, the team's manager won a Manager of the Year Award.Jim Riggleman managed the team for five years from 1995 through 1999, earning the team's first and only wild card playoff spot in 1998. Dusty Baker's Cubs lost in the 2003 NLCS during the first year of a four-year managing tenure. Baker's successor, Lou Piniella, led the team to two consecutive National League Central Division titles during his first two years with the team and was awarded the 2008 Manager of the Year Award. On July 20, 2010, Piniella announced his intention to retire as manager of the Cubs following the end of the season. However, on August 22, 2010, Piniella announced he would resign after that day's game with the Atlanta Braves, citing family reasons. Third base coach Mike Quade would finish the rest of the season as manager. The Cubs' current general manager is Jed Hoyer, who replaced Jim Hendry.
On November 7, 2013, the Cubs hired Rick Renteria as their new manager. He replaced Dale Sveum. He was fired on October 31, 2014 as the team prepared to hire Joe Maddon.
a The 19th-century World Series was a different event from the current World Series, which was first played in 1903. The 19th-century World Series was considered an exhibition contest between the champion of the National League and the champion of the American Association.