8. Zdeno Chara: $77,481,500
Despite being drafted in the 3rd round, the 6’9 defender managed to have a tremendous career captaining his current team, the Boston Bruins. Zdeno Chara became a very rich man during the off season before the 06-07 season, as the highly coveted free agent left Ottawa and signed a huge deal with the Bruins worth $37.5 million for a 5 year term ($7.5 mil per). Chara did not disappoint in his time with the Bruins, changing the team’s dynamic and identity. The tall defenseman was later resigned to another huge extension worth $45.5 million for a 7 year term ($6.9 mil per). Chara’s contract is set to expire during the 2017-2018 season, and he will be 41 when it comes to a close. Therefore, this may be Chara’s final NHL contract.