Cuban was born in Pittsburgh, Pennsylvania. His father, Norton Cuban, was an automobile upholsterer, while Cuban has described his mother, Shirley, as someone with "a different job or different career goal every other week." He grew up in the suburb of Mount Lebanon, in a Jewish working-class family. His paternal grandfather changed the family name from "Chabenisky" to "Cuban" after his family emigrated from Russia through Ellis Island.

On January 4, 2000, Cuban purchased a majority stake in the NBA's Dallas Mavericks for $285 million from H. Ross Perot, Jr. In the 20 years before Cuban bought the team, the Mavericks won only 40% of their games, and a playoff record of 21-32. In the 10 years following, the team won 69 percent of their regular season games and reached the playoffs in each of those seasons except for one. The Mavericks' playoff record with Cuban is 49 wins and 57 losses, including their first trip to the NBA Finals in 2006, where they lost to the Miami Heat. On June 12, 2011, the Mavericks defeated the Heat to win the NBA Finals. Historically, NBA team owners publicly play more passive roles and watch basketball games from skyboxes; Cuban sits alongside fans while donning team jerseys. Cuban travels in his private airplane--a Gulfstream V--to attend road games. In May 2010, H. Ross Perot, Jr., who retained 5% ownership, filed a lawsuit against Cuban, alleging the franchise was insolvent or in imminent danger of insolvency. In June 2010, Cuban responded in a court filing maintaining Perot is wrongly seeking money to offset some $100 million in losses on the Victory Park real estate development. The lawsuit was dismissed in 2011, due in part to Cuban asserting proper management of the team due to its recent victory in the 2011 NBA Finals. In 2014, the 5th Circuit Court affirmed that decision on appeal. Following his initial defeat, Perot attempted to shut out Mavericks fans from use of the parking lots he controlled near the American Airlines Center. In January 2018, Cuban announced the Mavericks would be accepting Bitcoin as payment for tickets in the following season.

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