As the Conference Finals portion of the 2026 Stanley Cup playoffs continues, Toronto Maple Leafs fans have been forced to look on as the rival Montreal Canadiens are now three wins away from a Cup final berth, and former Leaf Mitch Marner is currently the leading scorer in the postseason. While these may be tough pills for Leafs nation to swallow, there is still a lot of hope for the fan base, most notably, the No. 1 pick in this summer’s NHL draft.
Even apart from the draft, there is a lot of uncertainty for the Leafs heading into the offseason. Will they keep Auston Matthews and William Nylander? Will the team commit to a full rebuild? These are just a couple of the many questions that the hockey community is pondering more and more with each passing day. Some especially management-savvy fans on the internet have even taken it upon themselves to craft some potential offseason deals that the Leafs could potentially make, and these proposed trades range from seemingly small-potatoes trades to massive, franchise-altering, blockbuster deals.
With that in mind, we will be taking a look at three fan-crafted trade deals from Puckpedia’s Puck GM platform and discussing what we think of the trade overall, as well as the likelihood of it even happening.
Let’s begin.
Nylander heads to Broadway
Is there a timeline where the Leafs opt to keep Matthews but trade Nylander? User BigBoyBakker attempted to simulate this scenario in his mock trade, which sees the Leafs send Nylander to the New York Rangers in exchange for Alexis Lafreniere and Braden Schneider. The Leafs send out a 30-year-old known scorer in Nylander, for two 24-year-olds who have shown flashes of elite play, especially in the case of Lafreniere.
On paper, the trade gives the Leafs a good amount of flexibility. Even if Toronto decides to deal Matthews, Lafreniere and Schneider easily fit with the timeline of the player that the Leafs will more than likely select with the No. 1 pick, Gavin McKenna, in comparison to the older Nylander. Additionally, Nylander would be a decent piece for a Rangers team that has quite a few veteran players on their roster, and he could even be used as a trade piece by then if New York opts for a rebuild after finishing the 2025–26 season tied for the league’s third-worst record.
Sure, there are some intriguing qualities, but don’t get it twisted, the Leafs likely would not do this trade. Trading a guy who has nearly put up 100 points in a season in Nylander, for a relatively unproven young defenceman in Schneider and Lafreniere, who has yet to take that real leap from solid player to star, is very risky. Nylander is also heading into the third year of an eight-year contract, and if the Rangers choose to rebuild, that contract timeline may not compute. While Nylander in New York could work if the Rangers opt for more of a retool, the deal overall is just very unlikely.
Rielly hits the road
One Leaf who has always been in trade rumours in recent seasons is Morgan Rielly, and that has been no different this season, especially with the buzz of a potential rebuild in Toronto. Carrying on the Rielly trade trend is user HM1999, who proposes a trade that sends Rielly to the Presidents’ Trophy-winning Colorado Avalanche for centres Jack Drury and Ross Colton, as well as a 2026 fourth-round pick.
Through this trade, the Avalanche, who already have a very strong forward corps, shed some weight in favour of strengthening a defensive corps that already includes two-time Norris Trophy-winner Cale Makar, and if Rielly can play as he has in some of the better years of his Leaf career, he could add additional offence to the Avs. For the Leafs, they get off of Rielly’s expensive contract and gain two centres that could help on their depth lines, an area that the team struggled with this past season.
While we don’t really see this as a trade that the Avalanche would be jumping at the chance to make, because frankly, they don’t really need it, this is a more realistic look at what kind of assets the Leafs would likely be able to get on the upper end for a Rielly deal. But at the same time, the return, if Rielly does get dealt, will really depend on whether the team chooses to rebuild or retool.
The Matthews trade
Possibly the biggest question heading into this offseason is whether the Leafs will keep Matthews to potentially pair alongside McKenna or trade the franchise cornerstone and commit to a full rebuild. This trade by user OilyBoy17 gives a glimpse into what it could take to make the Leafs pull the trigger on a Matthews trade.
In this trade, the Leafs send Matthews and defenceman Brandon Carlo to the San Jose Sharks for Alex Wennberg, Tyler Toffoli, William Eklund, a 2026 fourth-round pick and the second-overall pick in 2026. This would give the Leafs the ability to draft both Gavin McKenna and someone like defenceman Chase Reid back-to-back in the upcoming draft, in addition to getting an excellent young player in 23-year-old Eklund, who has put up over 50 points in each of his last two seasons.
With this trade, the main piece is the second-overall pick, and honestly, that may not be enough of a selling piece to land Matthews in San Jose to play alongside young star Macklin Celebrini. If the trade included more young pieces like Michael Misa or Sam Dickinson, then maybe it would be a more worthy trade for Matthews, but who’s even to say that the Sharks would want to take that risk? While a Matthews trade isn’t out of the question, this template may not be enough for Toronto to pull the trigger.
