Front-runner for Leafs GM position has a checkered past that should make Shanahan think twice

The Flames qualified for the playoffs in 5 of those 9 seasons and advanced to the second round twice, but that's as far as they went. They had a couple 50-win seasons under their belt, but the coaching carousel did them no favours. Neither did their star players wanting out of Calgary.

With the Toronto Maple Leafs having money to burn this summer, it goes without saying that it is vitally important that they spend their money wisely. With close to $20 million in projected cap space, several holes to fill, and the looming expiring contracts of Auston Matthews and William Nylander on the horizon, they can not botch this very important summer. That in it of itself makes finding the right general manger that much more important. If Treliving is the guy that Brendan Shanahan believes in, maybe someone should point out his history with contracts and subsequent buy-outs first.

Compared to Kyle Dubas, Treliving has bought out 6 contracts in his 9 years to Dubas' 0. While Dubas didn't technically buy-out any contracts, he did make trades to rid the Leafs from the contracts of Petr Mrazek, Patrick Marleau, and Nikita Zaitsev, which also cost the Leafs some pretty decent assets. Pick your poison between Dubas shelling out futures or Treliving holding onto dead cap for several years - some during the flat cap era.

If the buy-outs weren't bad enough, lets also not forget that he traded a first round pick and 2 second round picks for Travis Hamonic, signed a 31-year-old James Neal to a 5-year deal worth $28.75 million, signed a 31-year-old Troy Brouwer to a 4-year deal worth $18 million, and overpaid to sign Blake Coleman after his Stanley Cup winning seasons with the Tampa Bay Lightning to a 6-year deal worth $29.4 million.

The Leafs have to worry about Matthews first and foremost. You can put your spin on the fact that they have the luxury of trading away William Nylander or Mitch Marner at their peaks, while still recouping a massive haul. However they need to address several positions of concern including a 1LW, 2C, 3C, and a top-4 defenseman if they can find one. Not everything that Treliving touched turned to stone but there are far too many red flags to not be concerned by Shanahan's attraction to the former Flames general manager.