19. Wade Redden

Year: 2008
Contract: $39 million/Six years
Team: New York Rangers
It was no secret that Wade Redden's numbers were on the decline in Ottawa as he entered free agency in 2008. So, why the Rangers thought he could somehow revive his career under the lights of the Big City we have no clue. As expected, Redden's numbers continued to drop and his time on the bench increased. Now the Rangers owe him millions through 2014. Is it us or do New York teams just love trickin' on overrated athletes no matter the sport?