The Chicago Cubs franchise began play as the Chicago White Stockings in the National Association when that league began play in 1871. They dropped out following the Great Chicago Fire, but rejoined the league in 1874. The team joined the new National League (NL) in 1876, and is the only team to play continuously in the same city since the NL was formed. The team's name transitioned through Colts to the Cubs, which had become standard by 1906.

The 1906 Cubs won a record 116 games in a 154 game season. The club then won back-to-back World Series titles in 1907-08.

During baseball's dead ball era, with many storied figures in the line-up, the Cubs won four pennants and two World Series titles over a five-year span. Although they fell to the White Sox in the 1906 World Series, The Cubs recorded a record 116 victories and the best winning percentage (.763) of the modern era. With this roster, Chicago won back-to-back World Series championships in 1907 and 1908. After losing star veteran catcher Johnny Kling for a season to the lure of pocket billiards, the Cubs finished a disappointing six games out of first place in the NL in 1909. However, with Kling back on deck in 1910, the Cubs once again reigned supreme in the NL, before going down to the Philadelphia Athletics in the 1910 World Series.

With new owner William Wrigley's money and William Veeck's front-office savvy, the Cubs were soon back in business in the National League, having built a team that would be strong contenders for the next decade.

The Cubs achieved the unusual accomplishment of winning a pennant every three years - 1929, 1932, 1935 and 1938. Unfortunately, their success did not extend to the post-season, as they fell to their American League (AL) rivals each time.

By 1939, the "double-Bills" (Wrigley and Veeck) had both died, and the front office, now under P.K. Wrigley, found itself unable to rekindle the kind of success that P.K.'s father had created, and so the team slipped into a few years of mediocrity.

The Cubs enjoyed one more NL pennant at the close of World War 2. Due to the wartime travel restrictions, the first three games were played in Detroit, where the Cubs won two games, and the final four were played at Chicago's Wrigley Field.

In game four of the 1945 World Series, the "Curse of the Billy Goat" was allegedly laid upon the Cubs when P.K. Wrigley ejected Billy Sianis, who had come to game four with two box seat tickets, one for him and one for his goat.

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