In 1999, after creating Broadcast.com to show live games and events over the internet for avid sports fans like himself (he was still following his alma mater), he sold the site to Yahoo! for $5.7 billion. Having completed this deal, Cuban made the decision to delve into basketball, one of his first loves, and purchased the Dallas Mavericks for $285 million from Ross Perot Jr. and company. The sale was finalized in February of 2000.

Since, he's been a very controversial figure in basketball, having paid over one million dollars in fines for opening his mouth and allowing unnecessarily negative words to fly, especially directed at game officials. In 2005, Cuban announced an interest in purchasing the National Hockey League's St. Louis Blues and Major League Baseball's Pittsburgh Pirates. He is also the owner of HDNet, the first high-definition satellite net

In 2004, he worked with ABC to produce a reality television series called The Benefactor, with 16 contestants playing games and participating in contests to compete for $1 million. However, the six-episode series was cancelled prior to all the episodes airing. Another claim to fame is Cuban's listing in the Guinness Book of World Records - he is credited with the largest e-commerce transaction, having paid $40 million for his Gulfstream V jet in October of 1999.

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