Brad Treliving’s Worst Trades Prior to Joining the Toronto Maple Leafs

Brad Treliving has already become somewhat of a polarizing figure since he joined the Toronto Maple Leafs, mostly due to some questionable spending. 

Toronto Maple Leafs fans will forever argue about just how successful Treliving’s predecessor was because while the team was constantly competitive under his watch, they ultimately didn’t win anything. 

Treliving has already put his fingerprints on his new team. He has filled out the front office and brought in fresh faces to compete on-ice in the likes of Tyler Bertuzzi, Max Domi, and Ryan Reaves.

Treliving spent nine years building and re-crafting the Calgary Flames. In that time, he made a number of blunders when trading talent. The following are his five most egregious trades.

Note: All statistics and trade notes are derived from Cap Friendly.

Toronto Maple Leafs: Treliving’s 5th Worst Trade

In 2022, Treliving traded Sean Monahan to the Montreal Canadiens for future considerations. The purpose of this exchange was just to get Monahan’s $6,375,000 cap hit off the books. That’s why he and the Flames were desperate to part ways with the forward.

What makes this a painful deal for Treliving is that he also had to include a conditional 2025 first round draft pick to get the Habs to pick up Monahan’s contract. Though Montreal was essentially paid to take Monahan, they liked what they saw from him before a groin injury limited him to just 25 games. He had already collected 17 points on six goals and 11 assists. Monahan re-signed with the Canadiens on a one-year $1,985,000 deal.

This trade looks worse for Treliving when considering how the Flames found themselves in a position needing to unload salary. It was by giving players like Monahan bigger contracts than deserved. It was actually Treliving who signed Monahan to his seven year $44,625,000 contract in Calgary.