32 Thoughts: Where things stand between the Maple Leafs and William Nylander

Toronto’s got two days off following Wednesday night’s “Escape from Dostal,” giving the organization a 48-hour between-game window to complete its William Nylander extension.

Obviously, everyone’s being very careful. No one wants to say the wrong thing. But, from multiple sources, here’s where we stand:

There’s a deal to be made, but things are “delicate.”

Toronto’s come a long, long way from last summer. Nylander, 27, bet on himself and is being rewarded — on-pace for career-highs in goals (43), assists (73) and points (116). He’s playing 20:24 per night, almost two minutes above his previous high, and was on the ice Tuesday while the Kings had an empty net late in Toronto’s best game of the season, a 3-0 win. That’s not exactly been a regular occurrence.

His Alfred E. Neuman “What, me worry?” personality is a major reason for this success; he’s unbothered by the discourse around him. 

Originally, the Maple Leafs hoped they could get this done for under eight figures ($10M), but those plans are at the bottom of some landfill. They accept this is going to be a massive deal. The question is: how massive?

Toronto wants this done. The Maple Leafs recognize his value, and would like certainty from him as they consider moves elsewhere around the roster. They are prepared to throw (even more) wads of cash at him.

“It would take a lot for me to want to leave Toronto,” Nylander said last August during the NHL/NHLPA Stockholm tour. Nothing he’s said or done since has made any feel differently, and while he won’t say anything publicly, he’s definitely receptive to what’s being offered.

This is a unique negotiation because of Michael Nylander. Honestly, I feel gross writing it because I hate bringing up family when it comes to this stuff. But it is a factor and why everyone is so careful in discussing where things stand. He plays a major role in these conversations and William is very loyal, as you would expect.

Again, the key principals are not talking, but there’s definitely feeling this will get done fast if there are four important yesses: team, player, agent and family. 

THOUGHTS

1. If you were tired of seeing the Blackhawks on Jan. 1, buy a comfortable pillow/blanket — because they are back.

This was a fun Winter Classic to attend. Great weather, great venue, Sir Mix-A-Lot, players ducking fish, Jack Sikma, Marshawn Lynch and Buoy being sent to Mascot Hospital. (Only complaint: I didn’t see Downtown Fred Brown.) You get caught up in the crowd’s excitement.

This was my 20th outdoor game, and it never fails. Unfortunately, the television numbers weren’t high in the United States, currently standing second in 2023-24 to Connor Bedard’s Opening Night debut. You think the NHL’s unaware of that? The word in Seattle was Bedard’s going to be involved next season, and since mentioning that on Monday’s pod, its become clear this is Chicago’s event to lose.

2. It’s always a great day when you get to talk to Tom McVie, but it was tough to hear him sad for the loss of a close friend, Connie “Mad Dog” Madigan, who died Tuesday. He was 89. In 1964, Madigan joined McVie on the old WHL’s Portland Buckaroos, starting a 60-year friendship. (That WHL was a senior league, not to be confused with the current junior loop.) Eight seasons later, Madigan would become the oldest rookie in NHL history, debuting Feb. 6, 1973, at age 38 for St. Louis.

McVie said Madigan was facing an uncertain future in the organization, and wasn’t thrilled with the possibility of leaving Portland for anywhere other than the NHL.

“I told him, ‘If you don’t go, they won’t care, you won’t get paid,’” McVie said. “So I called the Blues, and asked the person who answered if I could talk to Mr. Patrick. You could do that in those days.” That’s Lynn Patrick, who was the team’s vice-president. “I said I’m here with Connie, and he thinks he can help the St. Louis Blues. (Patrick) said, ‘You think you can help the St. Louis Blues?’ Connie said yes. ‘Well, then you better get your ass to St. Louis.’ I gave him a suitcase, and I haven’t gotten it back yet.” (McVie has a very distinctive laugh.)

Madigan played 25 games in the regular-season and playoffs, with three assists. That was it for his NHL career, but he played three more pro seasons and was a very good defender — making eight minor-league all-star teams. Once Don Cherry’s defensive partner, he has a hilarious cameo in Slap Shot as Ross “Mad Dog” Madison, giving the finger to the crowd while being introduced before the final scene.

“He was a legend,” McVie said. “He could remember when he worked on the pipeline as an 18-year-old, how many rivets he put in the pipe. But he couldn’t remember any guy’s name he played with. He’d spear me in practice, and when I complained, he’d say, ‘If you let up in practice, you’d let up in the games.’ During those, someone would be saying to him, ’You’re gonna get it, Madigan.’ He’d look at me and say, ‘Lot of guys have told me that.’”

McVie closed with a story about an off-day at a bar where Madigan told teammates that he’d carry a 170-pound canoe through forests to go fishing in the summer. They weren’t buying it, so, determining McVie weighed about that, Madigan was to carry him back to the hotel as proof. Before they arrived, the police pulled up.

“They told him to put me down, but he refused because he didn’t want to lose our bet. There was a lot of money on it. We said to him, ‘You win!’”

They were in San Francisco to play the hometown Seals when this occurred, and after explaining it to the police, one of them said, “I know what I’m going to do, I’m betting on the Seals tomorrow.” If there was one thing McVie was really happy about, it’s that Madigan was inducted to the Oregon Sports Hall of Fame in 2022.