The NHL trade deadline is a time for teams and their general managers (GMs) to prove themselves with moves that can potentially make or break a season. Teams are either sellers looking to bolster their draft picks and young talent, or buyers looking to spend what they can to improve their team for a run at the Stanley Cup a couple of months down the road. 

GM Kyle Dubas of the Toronto Maple Leafs is constantly under pressure from fans and media to improve his roster. However, considering it’s the final year of his contract combined with the lacklustre playoff performances of recent years, Dubas may have come into the deadline with a need to prove something to his higher ups and the fans that have been deprived of a second-round playoff series for nearly 20 years.   

The 2023 NHL trade deadline has shown that the Leafs are willing to do whatever it takes to win the playoffs. But is the risk worth the reward? Time after time, teams have gunned for a championship but found themselves hung out to dry the following season. The 2022 Tampa Bay Lightning gave up five draft picks — including two firsts — to bolster an unsuccessful playoff run. The 2019 Toronto Raptors traded star players DeMar DeRozan and Jakob Poeltl for superstar Kawhi Leonard and proceeded to win a championship, but they have underperformed since. 

Taking the risk to win has historically produced both successful and unsuccessful results. Even when a team wins the same season, they pay the price of future years of failure. But for the Leafs, going all in seems like the only option. Fans are tired of experiencing “decent” trade deadlines only to watch their team lose in the first round every year. The Leafs have their backs against the wall. They have exhausted every option to succeed — taking a big risk for the potential of a big reward might as well be their only option.  

On paper, the Leafs are all in. But what does that mean? It seems like the Leafs have mortgaged their future by trading away two first-round picks and five other future draft picks in exchange for a rental centre Ryan O’Reilly and other key pieces that may help them win this season. 

But, taking a deeper look into what wasn’t traded and adding some context to the trades may ease fans’ worries about the future.  

The most valuable assets the Leafs traded are easily the pair of first-round picks and Rasmus Sandin. Sandin, 23, is a promising but inexperienced defenseman. In trading him away, Dubas replenished one of the firsts he gave up in previous trades and opened up more playing time for the experienced Jake McCabe and Luke Schenn. 

McCabe may sneakily be the best pickup by Toronto; he’s a defense-oriented NHL veteran who will fill the slot nicely beside TJ Brodie on the second line. However, all eyes are on former Selke Trophy winner Ryan O’Reilly from the Blues. The 31-year-old centre solidifies the Leafs as one of the best offensive teams in the league on paper, while adding Stanley Cup experience and veteran leadership to the lineup. Unfortunately, he’s been placed on the injury roster for four weeks after surgery on his broken finger. 

Despite this, the Leafs still have a first-round pick in this year’s draft, and they kept prized prospect Matthew Knies, who may be able to make an impact in the NHL when he’s done playing with the University of Minnesota.

Dubas armed this Leafs team with everything they needed to not only make it past the first round, but also to win the Stanley Cup. The Boston Bruins are having an unbelievable season, and they, like many other teams in the East, strengthened their team at the deadline. It may be a tough road through the East this year, but like every other recent season, a first-round exit will be a disappointment for the franchise — as will anything short of a Stanley Cup.