3. Brad Richards: 85,781,556
You can thank the Tampa Bay Lightning and New York Rangers for Brad Richards being ranked so high on this list. Richards broke out early in his career with the Lightning. In 2004, he won the Conn Smythe Trophy, leading Tampa Bay to a Stanley Cup victory. The next season, Richards would impress once again, putting up a career high 91 points. This prompted the Lightning to sign Richards to a massive extension worth $39 million for 5 years ($7.8 mil per). Upon singing this big extension, Richards would end up getting traded in only the second year of his new contract to the Dallas Stars. After completing 2 good seasons with Dallas, the Rangers stepped up and gave the free agent a ridiculous 9 year, $60 million dollar deal. Richards, as you probably already know, did not live up to expectations and was bought out before year 4 of his 9 year deal. As you might also expect, Richards wasn’t too picky when it came to money, signing a one year deal worth $2 million with the Blackhawks this season.