Chicago Cubs
In 1902, Spalding, who by this time had revamped the roster to boast what would soon be one of the best teams of the early century, sold the club to Jim Hart. The franchise was nicknamed the Cubs by the Chicago Daily News in 1902, although not officially becoming the Chicago Cubs until the 1907 season. During this period, which has become known as baseball's dead-ball era, Cub infielders Joe Tinker, Johnny Evers, and Frank Chance were made famous as a double-play combination by Franklin P. Adams' poem Baseball's Sad Lexicon. The poem first appeared in the July 18, 1910 edition of the New York Evening Mail. Mordecai "Three-Finger" Brown, Jack Taylor, Ed Reulbach, Jack Pfiester, and Orval Overall were several key pitchers for the Cubs during this time period. With Chance acting as player-manager from 1905 to 1912, the Cubs won four pennants and two World Series titles over a five-year span. Although they fell to the "Hitless Wonders" White Sox in the 1906 World Series, the Cubs recorded a record 116 victories and the best winning percentage (.763) in Major League history. With mostly the same roster, Chicago won back-to-back World Series championships in 1907 and 1908, becoming the first Major League club to play three times in the Fall Classic and the first to win it twice. However, the Cubs have not won a World Series since; this remains the longest championship drought in North American professional sports.

Q: Who holds the longest championship drought in North American professional sports?
the Cubs