The NHL trade deadline week is one of the most exciting times of the season. This is when contenders bulk up for the playoffs, while sellers load up with draft picks and prospects. The Toronto Maple Leafs recent trade deadline history is consistent. Most of those times, they have been loading up to go on a playoff run. Unfortunately, it has never really worked out. This season, they will likely be sellers, as they currently sit outside of the playoff picture. So far, they have been quiet.
Let’s take a look at some significant trade deadline acquisitions the Leafs have had in previous years.
2025: Maple Leafs acquire Brandon Carlo from the Bruins
The 2025 trade deadline resulted in a key move for the Leafs. Brad Treliving attempted to bolster the defensive corps with the addition of right-handed defenceman Brandon Carlo. The veteran spent parts of ten seasons with the Bruins organization and was a key part of some successful seasons. In return, the Leafs sent prospect Fraser Minten, a conditional 2026 first-round pick, and a 2025 fourth-round pick (Vashek Blanar). This trade has certainly looked better for Boston so far.
Carlo has not quite been the force the Leafs were expecting. Since he joined the Leafs, he has blended into the defensive corps. Instead of bringing a physical presence and being a heavy shooter, he has been weak and a bit of a pylon. Boston got the best part of the deal in Minten. The young 21-year-old is having a breakout season. He has 29 points in 59 games, helping the Bruins push towards the playoffs.
Carlo has a good cap hit of $4.1M a season. The Leafs are only paying him $3.485M as the Bruins retained 15% in the trade. Carlo only has a year left after this season, so the Leafs could look to move him next year if they want. The experiment has been a failure for the Leafs.
2025: Maple Leafs acquire Scott Laughton from the Flyers
Another newsworthy trade that the Leafs made at the 2025 deadline was acquiring Scott Laughton, a 2025 fourth-round pick (Vashek Blanar), and a 2027 sixth-round pick from the Philadelphia Flyers. Going back to Philadelphia was prospect Nikita Grebenkin and a 2027 first-round pick. This was a trade that was worth it for Toronto, as Laughton had established himself as a reliable shutdown forward. The fourth-rounder acquired by Toronto in this trade was then flipped to Boston in the Carlo deal.
Laughton was a great addition for the Leafs. He has assisted on the penalty kill and is a reliable face-off guy. To this point, Laughton is having the best face-off-winning season of his career, with a phenomenal 56.4%. He has not provided much offence for the Leafs, but that really is not his job. In the 2025 playoff run, Laughton was the key face-off man, winning 57.1% of his draws. This, alongside his physical play, makes him a valuable member of any team.
The Flyers retained 50% of Laughton’s contract, so the Leafs have him at a cap hit of $1.5M. After this season, Laughton will be a UFA. If the Leafs do not end up re-signing him, this trade most likely will not be worth it in the long run. Grebenkin still has some solid potential and has had himself a decent rookie campaign. The young forward has four goals and twelve points through forty-five games.
2021: Maple Leafs acquire Nick Foligno from the Blue Jackets in a three-team trade
This trade was a rough one for the Leafs. Way back in 2021, the Leafs required some veteran assistance on their forward corps. Nick Foligno was acquired from the Columbus Blue Jackets, alongside forward Stefan Noesen, from the San Jose Sharks. The Leafs ended up sending a 2021 fourth-round pick to the Sharks, a 2021 first-rounder, and a 2022 fourth-rounder to the Blue Jackets. All of this led to one game from Noesen and eleven from Foligno.
This deal was an attempt to bolster the Leafs with some extra playoff experience ahead of the 2021 playoff run. The Leafs were set to face their rival Montreal Canadiens, in the first round of the playoffs. Foligno only played in four games that series, had one assist, and a fight against Corey Perry. This series ended in heartbreak as the Leafs lost Game 7, continuing their playoff woes.
In the following offseason, Foligno signed with the Boston Bruins. This was a two-year deal with a cap hit of $3.8M a season. Giving up three draft picks for two players who barely played was an awful move to take the Leafs into the playoffs. Their choke against the Canadiens was a typical result.
2021: Maple Leafs acquire David Rittich from the Flames
Another trade from the 2021 deadline that did not really hit expectations was when the Leafs acquired goaltender David Rittich from the Calgary Flames. The Leafs gave up a 2022 third-round pick (Aidan Thompson). The trade was one for one, and just like Foligno, Rittich barely played. Rittich appeared in four games after the trade and posted a 1–1–1 record alongside a .888 save percentage.
Rittich made his Leafs debut against his former team, the Flames. This was a close game that was capped off with a Johnny Gaudreau overtime winner against his old teammate. Rittich went on to get one win as a Leaf against the Vancouver Canucks. Then, in the offseason, he signed as a free agent with the Nashville Predators to a one-year deal.
Which one of these trades still haunts the Leafs the most? Are they in for another rough buying deadline? Or will they make the right decision to sell?
