May 1, 2014; Boston, MA, USA; The Boston Bruins logo is frozen in ice before game one against the Montreal Canadiens in the second round of the 2014 Stanley Cup Playoffs at TD Banknorth Garden. Mandatory Credit: Greg M. Cooper-USA TODAY Sports
3. Bobby Orr
It’s hard to fathom how arguably the greatest defenseman to ever play the game could ever be on a list with the word “worst” in it, but here we are and here’s how.
Bobby Orr was and still is a legendary Boston Bruin. He showed that defensemen could play offense, too. In 10 seasons in Boston, Orr put up 888 points in 631 games played. He won the Norris Trophy eight times, the Hart Trophy three times, the Art Ross twice, the Conn Smythe twice and the Stanley Cup twice. It doesn’t get better than that for a blueliner.
After recording 135 points in the 1974-75 season, Orr missed all but 10 games in the 1975-76 season. It would be his last as a Bruin.
Enter the ’Hawks.
The Bruins were ready to give up on Orr, believing that injuries had finally caught up to him. The ’Hawks, having struggled throughout the entire decade of the 1970s to that point, ponied up $3 million for the next five seasons. Seriously, that was a huge contract back then.
The ’Hawks believed that Orr would turn their franchise around, but they couldn’t have been more wrong. Orr played only 26 games over the next two seasons for the ’Hawks before retiring due to injuries.
Orr’s signing with the ’Hawks did nothing to his already astounding legacy, but it can be looked at as nothing more than a colossal bust for the Hawks.
Next: Second-Worst Free Agent Signing