Damian Lillard – $30 Million
Damien Lillard signed a monster contract with Portland—a $140 million deal that he has three seasons left of. This star NBA player sure has it going—he’s got Adidas releasing several signature shoes in his name and a best-selling apparel line. He gets a 10 figure annual salary to pitch their wares. On the side, Lillard is a rapper in the making, with two full-length albums in his music portfolio already. He spent $2.8 million on a luxury West Linn home a few years back.