No. 1: Jamie Oleksiak
In a perfect world, I'd love to see a defenseman who can provide offensive on the power-play, but in this case, I wouldn't really care.
If you look back at the last few teams who have won the Stanley Cup, all of them have had big nasty defenseman on the blue-line. And if you were to look up big defenseman in the dictionarry, you would find a picture of Jamie Oleksiak.
At 6-foot-7, 250 pounds, Oleksiak is one of the biggest defenseman in the NHL In my opinion, he should be one of the most sought after players for the Leafs this trade deadline and the team needs to pair him with Jani Hakanpaa, if he ever comes back healthy.
While there is a chance that this pairing would likely spend all their time being hemmed in the Leafs zone, but how much worse could they be than Benoit and Timmins? At least this incredibly huge pairing would make opposing players think twice about going to the Leafs net. With proper deployment, this could be an incredible weapon for coach Craig Berube.
Oleksiak is a left-handed shot, while Hakanpaa is a right-handed shot, so the two could play together and be the biggest defensive-pairing's in hockey.
Hakanpaa is 6-foot,7, 225 pounds, so imagine coming down the wing and trying to score in front of the net against those two guys? They would be unstoppable and could be a huge force in the playoffs.