When: 2007

Lighty was the architect behind many massive deals, but 50 Cent's Vitamin Water deal was his biggest deal ever. Not only did Lighty hook 50 up with Glacéau, but he was also the one who insisted on getting stock in the company. The demand paid its dividends when Coca-Cola bought out Glacéau for $4.1 billion, and 50 Cent caught the biggest check of his career, a reported $100 million.