Mark Cuban's Biggest Wins and Losses

PHOTO: Mark Cuban smiles as he stands outside the federal courthouse after a verdict in his insider trading trial in Dallas
LM Otero/AP Photo

Mark Cuban just beat the Securities and Exchange Commission and its accusation that the self-made billionaire engaged in insider trading. It's one of many victories in Cuban's storied business career, but he's taken his share of risks and suffered some major setbacks as well.

The SEC accused Cuban of selling 600,000 shares worth $7.9 million in search firm Mamma.com on non-public information. He is said to have avoided a $750,000 loss on the sale, according to the SEC, which brought a civil suit against him in November 2008.

Cuban, 55, is worth an estimated $2.5 billion, according to Forbes, but admitting guilt or settling could have been costly, even for him.

"Clearing his name and others accused of insider trading in court is very important," said Robert Heim, a former assistant regional director with the SEC's enforcement division and a partner with law firm Meyers and Heim LLP.

Read More: Mark Cuban Found Not Guilty of Insider Trading

The legal fight, which likely cost $1 million to $2 million in legal and attorney fees, was worth it for Cuban, Heim said. "I would say that it was well over the $750,000 in losses just given the prestigious firm he used and the amount that went into a trial."

If Cuban had settled with the SEC, he likely would have had to admit to committing securities fraud in the form of insider trading, which would exclude him from utilizing benefits in SEC rules for future business dealings.

Here are some other major bets that Cuban took, resulting in some wins and some losses:

Win

MicroSolutions

Cuban started systems integration firm MicroSolutions in 1983, which would be the first company he would sell. In 1990, he and his partner, Martin Woodall, sold it to H&R Block's CompuServe for $6 million. He became a millionaire at age 35.

He said he netted "about $3 million all in on that sale," according to an interview in2010 with the Kauffman Foundation.

Win

AudioNet

Cuban started Internet radio company AudioNet in 1995 with a fellow Indiana University graduate Todd Wagner, reportedly because they wanted to hear basketball games on the radio.

The company became Broadcast.com in 1998 and went public. Then Yahoo bought it for about $5.7 billion.

Win

Dallas Mavericks

It was in 2000 when Cuban "entered the national consciousness," according to Investor's Business Daily, when he bought the NBA's Dallas Mavericks team for about $285 million from Ross Perot Jr.

"Mark would not give up and I think I told him 'no' for about six months," Perot said, according to a team press release, but Cuban was a "very good salesman."

The team clinched the NBA championship in 2011, and today the team is worth an estimated $685 million -- the fifth most valuable NBA team, according to Forbes, which added that the team has "consistently lost money under Cuban thanks to high payrolls that triggered the luxury tax."

Win

HDNet

Cuban launched high-definition cable channel HDNet in 2001, which later aired mixed martial arts events. The new rebranded network, AXS TV, has the involvement of Ryan Seacrest Productions, sports and entertainment company AEG, and venerable Hollywood talent agency Creative Artists Agency.

Loss

Dancing With the Stars

Cuban and dancing partner Kym Johnston were the fifth couple to get the axe in the fifth season of ABC's "Dancing With the Stars." Whether it was a loss for Cuban and a win for the viewing public -- it's hard to say.

Loss

Major League Baseball

Cuban has reportedly had three failed attempts to purchase a Major League Baseball team -- the Chicago Cubs, Texas Rangers and Los Angeles Dodgers. He reportedly considered the New York Mets and Pittsburgh Pirates.

Loss

U.S. Supreme Court and Grokster

In 2005, Mark Cuban announced that he was financing the defense of Internet company Grokster before its case against MGM was argued before the U.S. Supreme Court. Cuban wrote in his blog at the time that he was approached by the nonprofit Electronic Frontier Foundation about the peer-to-peer lawsuit.

"If Grokster loses, technological innovation might not die, but it will have such a significant price tag associated with it, it will be the domain of the big corporations only," Cuban wrote. "It will be a sad day when American corporations start to hold their U.S. digital innovations and inventions overseas to protect them from the RIAA (Recording Industry Association of America), moving important jobs overseas with them."

The Supreme Court ruled in June 2005 against Grokster and Streamcast, saying they promoted file piracy.

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