No. 2: Erik Karlsson
Although they play the same position, I can't think of a more different defenseman than Oleksiak. Karlsson is a beautiful skating defenseman who drives offense and is a weapon on the power-play, while I don't know if Oleksiak has ever even played on the power-play once.
The idea of adding Karlsson may sound crazy to some, but I personally don't think that it is. I know the Leafs have a ton of skill upfront, but the biggest thing they're struggling with right now is breaking the puck out and moving it down the ice.
Tanev and OEL are decent puck movers, Rielly is a great puck mover, and Timmins is OK. The other three Leafs regulars (Benoit, Myers, McCabe) are well below average, meaing Erik Karlsson would do wonders for the NHL's most talented group of forwards.
Karlsson is two years removed from a 25 goal, 101 point performance and is still one of the best offensive defensemen in the NHL. Adding him to this Leafs line-up will only improve the team.
If your argument for adding Karlsson to the line-up is that he's offensive and doesn't help defensively, then you need to reevaluate that statement. If Karlsson is continuing to get the puck out of the zone, and skate it to the opposition's end, then that only improves their defense. The idea of defense isn't to block shots and hit people, but instead it's to control the puck and play in the other team's end as much as possible.
If you control the puck and stay in the other team's end, then it gives them less chances at scoring and helps the overall defense. I don't think fans have came around on this as much as they should and consider big hits as a better way of defense, but in reality, if you hit someone, it means you don't have the puck, and if you don't have the puck, you can't score, which is the name of the game.
Anyways, if Karlsson is on the table, the Leafs should explore the trade.