The Maple Leafs are on the brink of winning a first-round playoff series for the first time since 2004 but should the franchise and its fans treat this season as a success if they fall at the next hurdle?

Video Transcript

JULIAN MCKENZIE: A serious question. If the Leafs win that first round-- and I think you've kind of answered this in a previous episode before. But they win this first round in five, and they get dusted by Boston in four, how much more success is that season?

OMAR: Big. For me. For me.

AVRY LEWIS-MCDOUGALL: Oh, for you?

JULIAN MCKENZIE: OK. For you. For you.

OMAR: It is-- I said it. The minute I hear the second round begins, and the Leafs are-- I am good. I am fine. I'm-- now the organization might think differently, right? But for me, I am good.

I'm straight. I'm fine. I'm chilling.

I'm-- I will go through the-- actually, you know what? It'll be against Boston. I don't know.

JULIAN MCKENZIE: And if you get dusted by Boston, I can't imagine you feel all that good about that, because all that same experience you counted on to win that first round series, you should at least hope would get you a game or two. Maybe even three against the Boston Bruins. Maybe not three. Or-- I don't know.

OMAR: I mean, I think-- I don't think-- I think organizationally-- you don't make the deals you made just to win one round, right? I've been making the [INAUDIBLE] But like-- no. Do this. I still think you'd be like, OK, well that sucks.

I'm pretty sure they're like, they made their trades. They made their trades hoping that they could finally make it-- they could make it through Tampa. And then, put themselves in the best position to take Boston on. No. Who knows?

If Boston series goes the distance, then you have a team in Boston that went to battle with Florida if they end up extending it. And then, maybe it's, quote, unquote, easier. Who knows?

But I think organizationally-- I don't think they went around and that's it. I think if you have that perspective as a general manager in the NHL, then you shouldn't have your job. But for me, that would be cool.