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.

Treliving’s 4th Worst Trade

In April of 2021, Treliving had decided he was through with waiting for Sam Bennett to reach his potential. The Flames believed that Bennett was going to be a top player on the team when they drafted him fourth-overall in 2014.

Bennett looked good during the 2015-16 season. He recorded 18 goals and 18 assists in 77 games. His play then began to decline as did his production. When Treliving chose to cut bait on Bennett, the centre from Holland Landing, Ontario had played in 38 contests that season. Over that span, he scored just four goals and eight assists.

Bennett was traded to the Florida Panthers where he immediately transformed into the player the Flames always hoped he’d become. In the 10 remaining regular season games in 2021, Bennett recorded 15 points on six goals and nine assists. He was also a point-per-game player in those playoffs where he notched five points in five contests.

The strong play continued the following year when Bennett tallied 28 goals and 21 assists. This past season, Bennett once again reached the 40-point mark but his best output helped lead the Panthers to the Stanley Cup Finals. The center collected 15 points in 20 games in the playoffs. They came on five goals and 10 assists.

In exchange for Bennett, the Flames received Emil Heineman’s signing rights and a second round draft pick that was used to select David Goyette. While Goyette is still playing in the OHL for the  Sudbury Wolves, Heineman was placed on loan to Leksands IF in the Swedish Hockey League. He will likely be playing for the Laval Rocket in the AHL this coming season.

Treliving’s 3rd Worst Trade

In October of 2018, Treliving moved his then 24-year-old defenseman Brett Kulak to the Montreal Canadiens for two blue line prospects, Rinat Valiev and Matt Taormina.

Valiev may be a familiar name to Toronto Maple Leafs fans. He played 10 games for the Buds in 2015-16 and also spent three years with the Toronto Marlies. At the time of the trade, the left defenseman had played a total of 12 games in the NHL. Valiev never ended up cracking Calgary’s lineup. He played two seasons for Stockton Heat in the AHL before heading to the KHL.

Taormina had more NHL experience than Valiev when he was shipped to Calgary. He had played 59 total games in the NHL. Now retired, Taormina also never made it to the Flames. He remained active for only a single season playing with the Heat before hanging up his skates.

Treliving knew when he traded Kulak that he was giving up the best player in the exchange. Kulak had already played 101 NHL games but was bouncing back and forth between the AHL and NHL.

With Valiev and Taormina unable to make their ways back to the NHL, Kulak established himself as a solid bottom pairing defenseman who deserved full time minutes in the NHL. He is still in the league, playing an important role for the Edmonton Oilers. His current contract pays him an average annual salary of $2,750,000.

Treliving’s 2nd Worst Trade

The biggest mistakes in Treliving’s career body of work have been trading away picks that become established NHL players.

This is forgivable. He shouldn’t be blamed that a third round pick he traded away in February of 2017 to get defenseman Michael Stone turned into goaltender Stuart Skinner. With the Oilers, Skinner made the NHL all-rookie team and was the runner up for the Calder Memorial Trophy, the league’s rookie of the year award.

It’s just bad luck that that same trade also saw Treliving give up a fifth-round pick that was used to take another goaltender Akira Schmid. Schmid too has made his way to the NHL. He looks like he is on pace to have a very promising career with the New Jersey Devils.

It is, however, too painful in the Flames and Treliving’s history to ignore the deal that was made in June of 2016. That’s when Calgary acquired goaltender Brian Elliott from the St. Louis Blues for a pair of draft picks.

Elliott lasted just one season with the Flames before signing a new deal that took him to the Philadelphia Flyers. During his only season in Calgary, Elliott started in 45 games and had a record of 26-18-3. He was good. He had a save percentage of .910 and a goals-against average of 2.55.

Unfortunately for the Flames, that’s all they got out of the trade. On the other end, the Blues made out like thieves. They used the pick their received to select Jordan Kyrou in the second round, 35th overall, in the 2016 NHL Entry Draft.

Kyrou has already established himself as one of the better players in the NHL. Two seasons ago, he had a 75 point campaign. Last year, he had 73, which included 37 goals. Kyrou is so good that GM Doug Armstrong signed him to an eight year $65,000,000 deal in September of 2022. He has a $8,125,000 AAV.