How many more first-round picks can the Leafs get this deadline?

This wasn’t supposed to be how the Toronto Maple Leafs‘ season played out. After winning the Atlantic Division last year and losing in seven games in the second round of the playoffs to the eventual Stanley Cup champion Florida Panthers, the Leafs had plans to return to the postseason and make a deeper run towards the Cup.
With just 65 points through 62 games this season, and sitting in second to last place in the Atlantic Division, Toronto has fallen dramatically short of expectations. Now, general manager Brad Treliving is tasked with making the best of a bad situation by recouping as many future assets as possible before Friday’s trade deadline. He made his first sale on Thursday, shipping center Nicolas Roy to the Colorado Avalanche for conditional first- and fifth-round picks. With other trade candidates on the Leafs’ roster, we’ll see how much material Treliving can gather before the deadline.
On Thursday’s episode of Daily Faceoff LIVE, hosts Tyler Yaremchuk and former NHL goaltender Carter Hutton were joined by The Fourth Period‘s David Pagnotta to discuss which moves Toronto could make to follow up the Roy deal.
Tyler Yaremchuk: Roy gets moved today for a first. I would imagine that the Leafs are pretty happy getting that type of a return for Nicolas Roy. I’m sitting here like, man, if they got a first for him, could they get another one for (Scott) Laughton? Could they get another one for (Bobby) McMann? Could they get another for OEL (Oliver Ekman-Larsson)? There’s a chance for the Leafs to rack up assets here, no?
David Pagnotta: There is. That trade, I’m sure Treliving is going to flex a little bit on it, and say “Look, I got the first.” It’s top-ten protected, but with the Avs I don’t think anyone’s going to worry about that next year. I think he’s going to utilize that as a benchmark for a lot of his deals. I anticipate if they move OEL that a first-round pick or something of equivalent value will be part of that package, wherever it ends up, whether it’s Detroit, Boston, big gulp there for Leafs fans, Tampa, I mentioned the Ducks. I think Montreal at some point checked in.
With McMann, I know they’ve been pushing for a first in that retun. I don’t know if it gets there. I think if they were to allow a possible extension in place, that would probably secure it, but I don’t think that’s part of the equation yet, and I don’t suspect that they’ll go there. They still are going back and forth a little bit with his agent to see if they can maybe massage something, but we’ll see in the next 26 hours or whatever it is what happens here. With Laughton, you’re probably looking at a second-round pick and a prospect there.
You can catch the full discussion and the rest of Thursday’s episode here…