Here’s a guy who always was a favourite of mine. Nathan Dempsey.

I always hoped, knowing the chances were slim, that he’d stick in Toronto. Unfortunately it was never meant to be, despite many opportunities.

Dempsey was a steady blueliner with the St. John’s Maple Leafs for years. Fans loved him and flooded call-in shows and internet discussion boards with what they thought was reasoning as to why he deserved the shot in Toronto.

He could hit, shoot, and was steady around his own net, never afraid to take the body. Many thought of him as a rather solid puck-moving defenceman, able to move it out of his end with tape-to-tape passes and quick rushes up the boards. Solid as an AHLer, but could never dodge the questions hanging over his NHL abilities.

As a co-captain, he was always a fan-favourite in St John’s. For whatever reason, he never seemed to make the right impression with the top brass in Toronto.

Dempsey came right out of the WHL Regina Pats and played a couple playoff games in St. Johns in the 1993 playoffs. In the 9 years he was a part of the Leafs organization, he spent the vast majority with the Baby Leafs, and only played 48 in total in Toronto.

On July 12, 2002, Dempsey understandably jumped ship and signed as a free-agent with Chicago. He knew his chances to stay in Toronto seemed slim as was proven over and over, so he made the move to save a career. He ended up playing a couple seasons with the ‘Hawks, seeing action in most games, before spending a couple more years in both LA and Boston. Overall, the move out of the Leafs fold brought him opportunity to play at the top NHL level.

Last season, once again a free-agent at the tail end of his career, Dempsey found a new home playing for SC Bern in the Swiss Elite League. He played a good chunk of the season, and seemed to fit in well.

No word yet on whether he play another season overseas, but here’s hoping that he’s able to carry on his career another year or two.

Funny story I ran across a while back about Dempsey playing in an AHL All-Star game and being benched. Ron Wilson was the coach at the time, in 2002, and their team was up by a decent score, but Dempsey had been caught up the ice on a couple goals against, as is typical in any All-Star game. Since Wilson and each of the players get a $500 bonus for winning the game, he benched Dempsey – afraid that he’d cost the team more goals and possibly the money.

It’s likely the only time a player has been benched in an AHL All-Star game…