ST. PAUL, Minn. — “Do you want to make a deal?”



It was around 3:30 in the afternoon in Minnesota and 30 minutes from the deadline for William Nylander to sign and play in the NHL this season. Nylander was on the phone, calling Kyle Dubas to make something happen with almost no time to spare.



The Leafs general manager was camped out in his hotel room in St. Paul with the rest of the team’s front office. Once that call came from Nylander, with whom he’d spent months trying to win over during various phone calls, texts, and in-person meetings, he knew the two sides were finally on the right track to make a deal.



A signed copy of the six-year contract worth $41.77 million came back to the Leafs with eight minutes until the 5 p.m. ET deadline, and after some needed adjustments, was finally filed to the league with only five minutes to spare.



“The worst-case scenario would have been a technical glitch that prevented this...