1. Brad May

Position: LW First signed: 2005-2006 Initial salary: $675,000

Why? Just why? Why would you bring in somebody that every single fan hates? That’s exactly what the Avalanche did when they signed May.

When he played for the Vancouver Canucks, May infamously put a bounty on the head of Avalanche forward Steve MooreTodd Bertuzzi collected, ending Moore’s career. A lockout would follow, wiping out the 2004-2005 season. When the NHL took back to the ice next, May was a member of the Avalanche.

Never accepted by the fanbase, he was booed at home games for the entirety of his tenure in Colorado. In the middle of his second season with the Avs, he was traded to the Anaheim Ducks. In 64 total games with the Avalanche, he scored three goals and nine points, registering a minus-14 rating.

The Avalanche were ethically wrong to bring him in. The highlight of his Avalanche career was when they traded him out of town.