12. Sidney Crosby: $70,050,000
As you might expect, Sidney Crosby is the youngest player making this top 15 list, despite being only 27 years old. When you’re regarded as being the best player in the world, it’s no secret that you’ll eventually be a very rich man. Crosby cashed in immediately after his 3 year level entry deal, and Sid agreed to his first major contract before the 08-09 season, signing for $43.5 million for a 5 year term, an average of $8.7 million/year. Just a season ago, Crosby extended his stay in Pittsburgh, signing a ridiculous 104.4 million dollar extension. When Crosby’s contract expires in the 2024-2025 season, he will be the NHL’s highest career earner of all time.