10. Mark Cuban violates NBA anti-tampering rules

Year of Penalty: 2010
Estimated Total Fine: $100,000*
Mark Cuban is a man renowned for his ability to express his opinions, follow his own desires, and handle writing posthumous apology checks. But when the vocal billionaire owner of the Dallas Mavericks was called out for breaking the NBA’s anti-tampering rules in 2010, he went a bit too far.

Mark Cuban has broken NBA Anti-Tampering Laws. ©Image by Catherine Lotze/Getty Images
Kobe Bryant’s free agency is drawing near in the offseason, and Cuban hinted that having Kobe with the Mavericks would be fantastic. The league viewed this as the owner of a team interfering with a player who was signed to a different team. In addition to this $100,000 fine, Mark Cuban also paid over $3.1 million in penalties. This is impressive considering that Mark Cuban has a net worth of $4.5 billion.