The Toronto Maple Leafs hired Brad Treliving after experiencing their highest high followed by possibly their lowest low of the Auston Matthews era.

After finally breaking the curse and winning a playoff round for the first time in seven years with the ‘Core Four’, the Leafs found themselves against the Florida Panthers in the second round of the 2023 playoffs. At the time, they were more of a hungry underdog at the time rather than the playoff juggernaut they became known as. Despite the Panthers being the final team to qualify for a playoff spot that year, they made quick work of the Leafs and outclassed them in every department.

You could see the relief in then-general manager Kyle Dubas’ face as the team celebrated their first-round victory over the Tampa Bay Lightning. After years of trusting the process and banking on his guys, the results finally bore some fruits. And only two weeks later, he and the team mutually parted ways, with Treliving sliding into his spot. Let’s revisit the almost-three years of Brad Treliving as Maple Leafs general manager and look at how we ended up where we are today.

Kyle Dubas left the Maple Leafs organization on May 19th, 2023. Only 12 days later, the Leafs had a new general manager. It’s important to note that with Dubas’ departure being rather sudden and both the NHL draft and free agency only a month and change away, there was some pressure on the Leafs to act fast. Still, ~how~ fast the Leafs moved in on Treliving would be reflected on as a mistake down the line. The interview process was extremely quick, and the Leafs were linked to Treliving almost immediately after parting ways with Dubas.

Still, Treliving was well-prepared for the spotlight and aware of the temperature in the market. He showed up to his first press conference, spoke fondly about the opportunity at hand and about Dubas’ work with the team. He talked about the importance of re-signing Matthews, who had an expiring contract on the horizon, and he talked about getting tougher. It was encouraging to hear for Dubas’ critics, and it was enough to satisfy the skeptics for the time being.

“There’s been heartache and there’s been some frustration in terms of where we’ve been in the playoffs lately,” Treliving said at his press conference. “It’s a hard league. We’re going to try to keep putting ourselves in a position to keep knocking on the door, keep knocking on the door, keep knocking the door and eventually push through.”

Treliving executed his first transaction as Leafs general manager in late June when he inked a pair of Leafs depth forwards, David Kampf and Pontus Holmberg, to contract extensions. While the Holmberg deal was pretty standard for what he was as a player at the time, the Kampf deal was an overpayment. He signed Kampf to a four-year deal worth $2.4 million, a contract that he would play two seasons of in Toronto before the team found a way to squirm out of his deal. Not a great start for Treliving, but far from a legacy-defining move.

Day 1 of free agency was…rough. Everyone had the sense going into free agency that the Leafs would be looking to change the type of players they brought in, pivoting away from cheap bargain bin options with good underlyings in favour of household names with intangibles. His first signing of the offseason was a three-year contract for veteran enforcer Ryan Reaves, a move that was criticized by lovers of analytics and praised by your Uncle. He followed that up by signing John Klingberg to a one-year contract, which didn’t do much to settle anybody’s nerves. Treliving made up for it on day 2 by signing Tyler Bertuzzi and Max Domi to one-year contracts, which satisfied a good portion of the fanbase and their uncles who grew up watching Todd Bertuzzi and Tie Domi.