The Toronto Maple Leafs drafted Tomas Kaberle in the 8th round and he went on to be the team's best defenseman since Borje Salming.
The Toronto Maple Leafs haven't turned a late pick - or even one lower than Nylander at 8th overall - into a superstar in almost 30 years.
They are overdue.
The Tampa Bay Lightning drafted Braydon Point in the third round.
The Toronto Maple Leafs Continue to Wait for Their Brayden Point
Pittsburgh had Kris Letang, Chicago had Duncan Keith, LA had Jon Quick, Vancouver had Alex Edler, and Detroit had Pavel Datsyuk, the Bruins had Patrice Bergeron and the Avalanche had Devon Toews (a 4th rounder they traded for while he was still considered a 4th rounder).
Every single team that has opened up an extended window of Cup Contention in the post-cap era of the NHL has hit on an unexpected superstar player.
Every single team, that is, except the Toronto Maple Leafs who have made the NHL Playoffs for eight straight seasons and been a top contender for at least five or six years now.
The Toronto Maple Leafs are built around a bunch of high-end draft picks, but how good would they be / have been if they had hit on another superstar?
Of course, this team has been haunted for years by the bad drafting it did outside the first round during the years when they were selecting their superstars.
But now maybe things are looking up.
Joseph Woll, Nick Robertson and Easton Cowen are all late picks that could potentially become superstars for the Toronto Maple Leafs.
Goalies are mercurial, but maybe Joseph Woll has what it takes to be the next Connor Hellebuyk.
Nick Robertson's brother is an MVP-level superstar and he's shown that he can score goals in the NHL at the very least. His potential is off the charts, but who knows if he will hit it.
Perhaps the best bet is Easton Cowen, who has now scored a point in 42 straight games in the OHL. Cowen was a first round pick, but he was 28th overall and it was conidered a stretch at the time to take him.
Sure, it's not exactly like finding a hall of famer with a 7th round pick like Detroit did with Datsyuk, but 28th overall picks do not generally become star players.
And maybe it's not Cowen. Maybe it's Fraser Minton or maybe it's Topi Niemela, who knows? The point is that the Leafs have been pretty unlucky when it comes to hitting on late-round star players, and that every other team that has reached their level in the cap era has one.
The Toronto Maple Leaf are waiting for their Bradyon Point.