Triple H – $150 Million

He started out as a wrestler in the early ‘90s, and by now, he’s become the WWE’s Executive Vice President of Global Strategy & Development. Triple H has managed to climb the ranks in the wrestling industry, and now there’s talk about him possibly inheriting the entire company from his father-in-law. He got married to Stephanie McMahon, a fellow wrestler, in 2003. She also happened to be his boss’s daughter! He’s worth $150 million right now, lives in a $30-million Connecticut mansion with his wife and three children, and drives around in a $96K-worth Cadillac Escadale.