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Hindsight is always 20/20 and in an excerpt of a new book by The Athletic’s Craig Custance, former Maple Leafs GM Kyle Dubas admitted that the most critical error the he made during his six-season tenure in Toronto was being proactive in locking up the club’s young core group in his first season.
“The biggest mistake I think I’ve made in my whole time here has been not taking care of the three incumbent contracts,” Dubas said to Custance as reported by Lance Hornby of the Toronto Sun. “(William) Nylander was up, (Mitch) Marner and (Auston) Matthews could have been done on July 1 extensions.”
Instead, the Leafs signed center John Tavares to a seven-year, $77 million free agent contract, let Marner and Matthews continue into the final year of their entry-level contracts, and kept Nylander as a holdout restricted free agent until he signed in December 2018.
Dubas said that while he spoke to Nylander, Marner, and Matthews representatives before the signing of Tavares on July 1, 2018, he did not make enough significant progress and that once the current team captain was signed to an $11 million AAV, it changed the nature of the negotiations.
“The thing I learned was once we signed John to the (AAV) we did, it lifted the lid on the entire ceiling,” Dubas said.
The Leafs had an opportunity to trade the unsigned Nylander before the December 1 signing deadline (reportedly to St. Louis for defenseman Alex Pietrangelo), but did not and instead signed him to a six-year deal that averaged under $7 million. Matthews followed two months later with a five-year deal at the second-highest paid contract below Connor McDavid ($11.634 million AAV), and last by Marner at the opening of the 2019-20 training camp for $10.9 million per season.
While Dubas was indeed culpable in the Leafs current predicament by not trading Nylander before signing him, the first error was made by his predecessor Lou Lamoriello, who in the summer of 2017 did not extend the young Swede coming off a 61-point sophomore season and entering the final year of his ELC.
Dubas’ biggest error was capitulating to Nylander, Matthews, and Marner in negotiations by not getting all of them locked up on the maximum term of eight years. Toronto was given no bargain in terms of salary on the shorter-term deals that they negotiated and they are still feeling the ramifications of that to this day.
Toronto Maple Leafs Blogger • 
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