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Chicago Bears Football Club operates the storied Chicago Bears professional football team, which lays claim to nine National Football League titles (its last in Super Bowl XX at the end of the 1985 season). More than 25 Hall of Fame players have graced the roster of "Da Bears", including Red Grange, Dick Butkus, Gale Sayers, and Walter Payton. Loyal Chicago fans root on their team at venerable Soldier Field. The franchise, originally known as the Decatur Staleys, was a charter member of the NFL in 1920. Chairman Michael McCaskey (grandson of founder George "Papa Bear" Halas) and his family control the club.

One of the Original Six professional hockey franchises of the National Hockey League, the Chicago Blackhawks boast a long history that includes four Stanley Cup championships and a roster that has featured such Hall of Fame players as Phil and Tony Esposito, Bobby Hull, and Stan Mikita. The club won its most recent NHL championship title in 2010, breaking a drought that lasted 49 years, the longest in league history. Loyal fans support the team at Chicago's United Center. The Wirtz family has owned the Blackhawks franchise through their Wirtz Corporation since 1954.

Chicago National League Ball Club operates the Chicago Cubs franchise of Major League Baseball, which has gone without a World Series title since 1908. The team was formed as the Chicago White Stockings in 1876 and bore several monikers (Colts, Orphans, Spuds) before settling on the Cubs in 1907. Despite the lack of championships, Chicagoans still flock to famed Wrigley Field (the second-oldest ballpark in MLB, after Boston's Fenway Park) to see their Cubbies play. A group led by billionaire Tom Ricketts acquired a majority of the Cubs in 2009.

Chicago Professional Sports owns and operates the Chicago Bulls professional basketball team, which boasts six NBA championships thanks to five-time MVP Michael Jordan. His charismatic presence not only set a high-water mark for Chicago between 1991 and 1998 but also helped increase the popularity of the league. The team was started by Dick Klein and joined the National Basketball Association in 1966. Real estate developer Jerry Reinsdorf has owned the Bulls since 1985. He also owns Chicago's United Center (along with Chicago Blackhawks owner the Wirtz Corporation) and the Chicago White Sox baseball team.

Chicago White Sox franchise is one of the oldest clubs in Major League Baseball, having joined the American League in 1900. The team boasts just three World Series championships, two from the early 1900s and it latest in 2005. (A World Series appearance in 1919 was marred by the "Black Sox" scandal that saw eight teammates banned from baseball for throwing the championship.) Playing host at US Cellular Field, the White Sox franchise is owned by real estate developer and chairman Jerry Reinsdorf, who also owns the Chicago Bulls basketball team.

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