A looming Boston draft threat perfectly forces Toronto to avoid another Kessel and Rask disaster
Photo credit: Tom Szczerbowski-Imagn Images; Perry Nelson-Imagn Images
While not a 1:1 comparison, if the Maple Leafs were to lose out on both an elite forward or defensive prospect to the Bruins — it could harken back to a scarier time.
As the days tick away until May 5th, the anticipation is growing surrounding the Toronto Maple Leafs and the draft lottery. With a chance to find themselves a franchise forward or defender who could change their fortunes immediately; it's a very exciting time.
It's also an extremely anxious time for Maple Leafs fans knowing that there is a very good chance that the team won't even get the pick and it'll head to the Boston Bruins courtesy of the rushed Brandon Carlo deal that has blown up in their face.
Blackhawks could go a bit off the board leaving Toronto free to draft their franchise blueliner
Luckily for them there is still a shot at getting a franchise player, and while adding someone like Ivar Stenberg or Gavin McKenna would be an incredible get, the team should focus on adding the replacement for Morgan Rielly in either Chase Reid or Keaton Verhoeff.
They could have one of them fall into their lap too. It's been rumoured that the Chicago Blackhawks are very interested in drafting Caleb Malhotra, and with Stenberg and McKenna expected to go in the top two, that leaves Toronto with a chance to snag either blueliner:
I think Chicago has had a lot of eyeballs on Caleb Malhotra all season long. - Jeff Marek, Sekeres & Price
Though, there is a case that Toronto could lose out on both adding Malhotra and a defender — which brings us back to the same scenario.
Losing out on a star player or potential future star is not unknown to the Maple Leafs considering they have already been burned three times by the Bruins in the last 20 years.
Why Boston taking Toronto's pick hurts, but prevents future issues
First, they traded Tuukka Rask for Andrew Raycroft and while at the time it was seen as a good move considering Raycroft was one of the top goalies in the NHL, he didn't even come close to his Boston numbers.
We know how Rask turned out in Boston, leading them to a lot of success and being one of the top goaltenders in the NHL. He finished his career with a 308-165-66 record along with a 2.28 GAA and .921 SV% and won the Vezina in 2013-14.
Then it was Phil Kessel being brought in to add some much needed offensive help, but the fact they traded away two picks that turned into Dougie Hamilton and Tyler Seguin; it's a rough deal in hindsight.
Kessel wasn't bad for Toronto but it's hard to imagine they wouldn't be better with both Seguin and Hamilton in the fray, and there may have been a world where both men are on the same team as Auston Matthews, Morgan Rielly, William Nylander and Mitch Marner (at the time).
The trifecta was the Carlo deal, but let's call a spade a spade. Boston has fleeced Toronto and they need to learn their lesson.
If you lose your pick to Boston, then you cut your loss and realize your mistakes then proceed to delete all contact info; never calling them again.
If you keep your pick and Chicago goes with Malhotra, then it's a franchise blueliner for Toronto.
The Maple Leafs already made the trade that likely cost them their first-rounder in 2026. You can't change the past or what the cards hold, but you can choose how to react to the situation.
May 5th can't come soon enough.
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