Thirty-three years ago, the Toronto Blue Jays reminded the city what it was like to be a winner. One person who definitely seemed to appreciate that winning in Toronto was special was Cliff Fletcher.

Fletcher had already been putting in work for the Maple Leafs in the post-Ballard era with the drastic franchise changing move that brought Doug Gilmour from Calgary, a Leafs trade that seemed to follow in the path of the Joe Carter and Roberto Alomar trade the Jays made a couple years earlier that would be the foundation for their World Series success. Even the Argos had found championship success with the high profile acquisition of Rocket Ismail in the early 90s and Fletcher wanted to add to the Championship vibes in the city.

Following the Blue Jays’ first World Series win, Fletcher brought in John Cullen from the Hartford Whalers. Cullen was a close to a point per game player in 1992-93 for the Leafs and had to ton of success in Pittsburgh and initially in Hartford as well. Cliff was swinging for the fences and followed that move up with acquiring Dave Andreychuk for Grant Fuhr. Andreychuk would score 29 goals in 31 games for the Leafs after his arrival that season and would be a 53 goal scorer the next year. Fletcher was committed to building a winner.

Fast forward 33 years and the Jays were within an inch of being World Series champions once again. And for a brief moment the city of Toronto was near the euphoria experienced by the Raptors win in 2019. The excitement of being that close to a World Championship shouldn’t be lost on this market, and while the Conference Finals runs that Cliff Fletcher did his part to provide the city with in 1993 and 1994 were some of the best hockey the Leafs have played in the past 50+ years, the Maple Leafs still don’t seem close to providing Toronto with the sports moment it seemingly craves the most, a Stanley Cup run.

It’s in that spirit that you’d hope that Brad Treliving might summon is inner Cliff Fletcher and also take note of what a legitimate contender means to this city. In some ways Treliving has already done half the work by casting off his Gary Leeman link to the past in Mitch Marner, but at no point has Treliving entertained the idea of bringing in a Doug Gilmour level player. A John Cullen level player. A Dave Andreychuk level player. And certainly, the Leafs are not into Mats Sundin territory yet either. It’s hard to take the Leafs interest in a cup run serious when the last four forward acquisitions are bottom-six forward castoffs from non-playoff teams.

The broken record keeps on playing the same lines over and over again but Treliving needs to aim higher, take some risks, and be willing to put a target on his back. There might only be 32 GM jobs in the NHL, but having a fortune to fall back on seems like an opportunity to do more than count Scott Laughton and Joel Edmundson trades as bold moves.

When you look at Toronto’s best teams you can see that bold moves preceded the successful runs. In the NHL, you can look at Bill Zito, Kelly McCrimmon, and Tampa era Steve Yzerman as General Managers not afraid to make bold moves who picked up Stanley Cup rings as a result. Being timid and thinking small can get you into the playoffs every year and not much else. And when the Blue Jays have just given evidence of what extended playoff run looks like in Toronto, you’d hope that Treliving is a GM who wants to make that moment happen for the Maple Leafs.