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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.

The Cincinnati Bengals professional football franchise traces an elite heritage, having been formed by Hall of Fame coach Paul Brown in 1968 as part of the American Football League (AFL). Cincinnati joined the National Football League in 1970 when the AFL and NFL merged and went on to make two trips to the Super Bowl (losing both times to the San Francisco 49ers). The team plays host at Paul Brown Stadium, which opened in 2000. Brown's family, led by his son Mike Brown, continues to control the Bengals.

The Cleveland Browns Football Company owns and operates the Cleveland Browns, one of the more storied franchises in the National Football League. Started in 1944 by Arthur McBride as part of the All-American Football Conference, the club joined the NFL in 1949 and boasts four championship titles, its last in 1964. The present team was awarded to the late Alfred Lerner and former 49ers president Carmen Policy after Art Modell relocated the original Browns to Baltimore in 1996. (A deal struck with the NFL allowed Cleveland to retain the team name, colors, and history.) Lerner's family, led by son Randy, continues to control the team.

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