The Cubs, playing in their eleventh World Series and their first since 1945, won their third championship and first since 1908. It was the Indians' sixth appearance in the World Series and their first since 1997, with their last Series win having come in 1948. The two teams entered their matchup as the two franchises with the longest World Series title droughts, a combined 176 years without a championship. Cleveland manager Terry Francona, who had previously won World Series titles with the Boston Red Sox in 2004 and 2007, fell short in his bid to become the third manager, and the first non-Yankee manager, to win his first three trips to the Fall Classic, after Casey Stengel and Joe Torre.
The Cubs were the sixth team to come back from a three games to one deficit to win a best-of-seven World Series, following the 1925 Pittsburgh Pirates, the 1958 New York Yankees, the 1968 Detroit Tigers, the 1979 Pittsburgh Pirates, and the 1985 Kansas City Royals.
The Cubs made their eleventh appearance in the World Series; their only previous two championships were in 1907 and 1908, both against the Detroit Tigers. They lost their eight other appearances, in 1906 against the Chicago White Sox, in 1910 against the Philadelphia Athletics, in 1918 against the Boston Red Sox, in 1929 against the Athletics, in 1932 against the New York Yankees, in 1935 against the Tigers, in 1938 against the Yankees, and in 1945 against the Tigers.
The Cubs qualified for the postseason by winning the National League Central, ending the regular season with the best record in the major leagues (103–58) for the first time since 1945; they also posted their highest winning percentage since 1935, and won their most games since 1910. The division title was their sixth since division play began in 1969, and their first since 2008. They defeated the San Francisco Giants in four games of the NL Division Series before clinching their first NL pennant since 1945 with a sixth-game victory over the Los Angeles Dodgers in the NL Championship Series.
For Cubs manager Joe Maddon, it was his second appearance in the World Series as manager – in 2008, he managed the Tampa Bay Rays when they beat the Boston Red Sox in seven games to win the AL pennant, then were defeated in five games by the Philadelphia Phillies in the World Series. It was also Maddon's third World Series appearance overall – in 2002, he was bench coach with the Anaheim Angels when they won the World Series in seven games.
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