TORONTO — When Mark Hunter is asked if he saw the difficulty of getting William Nylander’s signature on his next contract coming months ago, the former assistant general manager of the Toronto Maple Leafs nods in agreement.

“Mmm hmm,” Hunter said Monday to a handful of reporters at the PrimeTime Sports Management Conference.

“That’s a tough, tough situation now, guys.”

The Leafs’ Nylander, a 22-year-old who used to play under Hunter, is a restricted free agent swimming deeper into uncharted waters.

If he’s not signed by Dec. 1, he will be ineligible to play in the National Hockey League this season, and Toronto GM Kyle Dubas is gathering information regarding his potential trade scenarios.

Dubas has maintained that he’d prefer to get Nylander signed. The GM declined comment on the state of negotiations Saturday night in Boston, via a team spokesperson.

Dubas was selected by president Brendan Shanahan over Hunter for the Leafs GM role in May after Lou Lamoriello’s contract expired. Both had been serving as assistant GMs under Lamoriello.

Hunter mutually terminated his contract with the Leafs shortly thereafter and returned to preside over the London Knights, the OHL team he co-owns with his brother Dale.

Hunter described the issue of getting the Maple Leafs’ trio of young, extension-eligible star forwards—Auston Matthews, Mitchel Marner and Nylander—all inked to long-term deals as a “big, big” challenge.

“It’s easy to always look back at things, but spring was the time,” Hunter said. “It’s tough. He’s got a lot of work to do on those three players.”

Though not directly linked to the Nylander impasse, a conference panel on player analysis that featured Hunter discussed issues of player entitlement and invasive parents. A reporter later raised those subjects in a discussion with Hunter regarding Nylander.

“But he’s a helluva player, too,” Hunter countered. “It’s easy to say it. Everybody says, ‘Trade him!’ Yeah? Trade? What are you going to replace him with? He’s a good player.”

Prior to the stalemate, Nylander — a winger with centre potential — posted consecutive 61-point seasons and had established himself as a dangerous complement to Matthews on the Maple Leafs’ first line.

Yet in two trips to the playoffs, these young, talented Leafs are still on a quest to reach the second round as their entry-level deals expire.

“He’s a top-end player,” Hunter stressed. “Everyone talks about one playoff round, but one playoff round is not going to define a top-end star player like him.”

Considering Hunter hasn’t spoken much publicly since severing ties with the Maple Leafs, we gathered below a few of the highlights from the experienced hockey man, who touched on a number of topics Monday.

Leafs president Brendan Shanahan never wanted to draft safe:

“Shanny, from the top of the grid, he’s been very good from the start. He wants to go for it. He doesn’t want, ‘Well, maybe he’s going to be a fourth-line player or a fifth, sixth defenceman.’ If we talked that way, my scouts, the hammer would come down. He didn’t like it.”

Lou Lamoriello’s appetite for analytics is stronger than you think:

“He kept notes on past things a player’s done, from scoring to shots. It shocked me how much notes he kept that backed up that player.”

“He was constantly taking notes. The Corsi, he followed. Puck possession, he was all into it. I shouldn’t even be telling this secret about him [laughs] because you know how secretive he is.

“I see some people say that about him. I go, ‘No.’ He’s all over statistics of kids’ age. That stuff’s on his table Monday morning — every statistic around the whole world, and he goes through it.

“That’s why he was successful in what he was doing, because of how he looked at everything. I don’t think some of the older guys get credit for doing that.”

There is a difference between old-school and new-school NHL executives:

“I just think sometimes the old school was a lot more quieter, and the younger school talks a lot more about what they’re going to do and how they’re doing things. Lou didn’t talk about himself, guys. He needs credit where credit’s due. That’s why he’s still in the business.

“Lou was a very quiet guy. There’s not too many secrets out there; he keeps his things very close. That’s from the old to the young, I think sometimes in the business, I think you can keep things closer to what you’re doing. You don’t have to tell everybody how smart you are. A lot of young guys in this business want to show how smart they are, instead of just showing what you got in the product you got on the ice.”

Marner’s desire to win could lead to more responsibility with the Leafs:

“He wants to be the guy — and that’s a credit to him. He wants to have a leadership role, which I think more and more in time, they’ll give him more of that, and I think he’ll even blossom more if they give him more of a leadership role.

“He gets passing too much. The goalies and teams will sit on ya, right? So he has to make sure he shoots, and his shot has gotten better. He still needs to work on it. I think in time he’ll move that to when to shoot and pass.”

Lamoriello had a direct link to the Maple Leafs players:

“Everybody thinks Lou just stands back. He’s constantly talking to players, guys. He’s even texting the players. I sat beside a 75-year-old guy who’s involved in texting back and forth with young men. It’s impressive.

“I’m sure Duby and Babber [Dubas and coach Mike Babcock] have that same level. Lou and Babber talked constantly. Lou — anybody who says he doesn’t communicate? Well, he does. He really does. You’d be surprised.”

The Senators’ Uber confessions were not a shocker (note: Alex Formenton, one of the Sens in the carpool, plays for Hunter’s Knights):

“What do you think management does after games? They’re talking about players—who’s done this, who’s done that. What the hell’s wrong with that guy? That’s why I kinda laughed at the whole thing.

“At the end of the day, both sides have people talking back and forth…. Babs — not just Babs but any coach — would talk about ‘Well, that player didn’t play well.’ Lou was very calm after games. He wouldn’t get involved. It was interesting, and he’s done a good job on the Island. I think it was good for him, the change. I think it reinvigorated him.”

Don’t take it personally if you whiff on a draft pick:

“You are going to make mistakes in the draft. The percentage of kids that are playing from the drafts, it’s going to happen. We can sit there and look at [Carolina forward Sebastien] Aho and [Toronto defenceman Travis] Dermott. Dermott went one spot ahead of Aho [34th and 35th in the 2015 draft]. Aho’s a good player. You could sit there and analyze it. Now, we had Marner. Did we need another Aho? But, you know what, we didn’t draft Aho. You can sit and look back at drafts and say, ‘Where did I screw up?’ But I think a problem with a lot of teams, in my personal opinion, is people take it too personally and sit there and analyze: ‘Where did I go wrong?’”

Hunter missed being around the London Knights but is open to an NHL front-office return:

“We all know how hard it is to get in, in the right position. Yeah, you always look at things, but it has to be the right position, the right situation.

“You’re always around listening, what’s going on in the game of [NHL] hockey.”