THN.com/podcast. From THN On The 'O': The OHL's NHL Draft Recap and 2024 Eligibles to Watch William Nylander [https://thehockeynews.com/.image/c_fit,h_600,w_600/MTk5NDk1MjA5ODkxOTMyMTEw/usatsi_20628983.jpg] William Nylander Toronto Maple Leafs GM Brad Treliving is currently engaged in contract extension talks with Auston Matthews [https://puckpedia.com/player/auston-matthews] and William Nylander [https://puckpedia.com/player/william-nylander]. During a July 18 appearance on the NHL Network, Sportsnet's Elliotte Friedman [https://www.youtube.com/watch?v=ffVJzbJYvrI&t=3s&ab_channel=NHLNetwork] reported Matthews and Leafs management could be closing in on a three- to five-year contract, though there's no word as to what the average annual value will be. As for Nylander, Friedman said their discussions remain at a standstill. That's little changed from TSN's Chris Johnston's July 3 report [https://thehockeynews.com/nhl/toronto-maple-leafs/news/report-contract-negotiations-between-maple-leafs-and-william-nylander-not-going-well] indicating the 27-year-old winger's contract talks “weren't going well.” Johnston said Nylander sees himself as a $10-million player while the Leafs were offering between $8 million and $9 million annually. That's quite a pay raise over his current cap hit of about $6.962 million. Nylander makes a good case, as he's coming off back-to-back campaigns of at least 80 points while seeing second-line minutes. Friedman pointed out he won't take less to stay in Toronto if other teammates won't. On July 4, Sportsnet's Nick Kypreos [https://twitter.com/FAN590/status/1676310953552429056] pointed out there won't be enough money to re-sign Mitch Marner in 2025 if the Leafs meet Nylander's asking price. His co-host Sam McKee believes they'll have to trade Nylander because they can't risk losing Marner. The Athletic's Jonas Siegel [https://theathletic.com/4685792/2023/07/14/maple-leafs-william-nylander-contract/?source=emp_shared_article] noted it feels like Treliving must sign or trade Nylander. However, he felt that a third option is keeping the winger for the coming season, competing for the Stanley Cup, and hoping to re-sign him before July 1. Treliving went through a similar situation as Calgary Flames GM in 2021-22 with Johnny Gaudreau, only to watch the winger depart to Columbus as a free agent. He could be reluctant to risk the same thing happening with Nylander.