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    Evan Doerfler·Jul 10, 2024·Partner

    ‘Matt Roy Was A Little Bit Of The One That Got Away’: Maple Leafs Were Reportedly Interested in Now-Capitals Defenseman, But Deal Never Came to Fruition

    Roy signed a lucrative six-year, $34.5 million contract with the Washington Capitals as NHL free agency opened up.

    The Maple Leafs made long-term commitments to Chris Tanev and Oliver Ekman-Larsson. Is it enough to remake the look and feel of Toronto's defense?

    Ahead of the opening of NHL free agency and with nearly $20 million to play with, the Toronto Maple Leafs had their hopes set on attacking “two really good” defensemen to add to their defensive repertoire. As we now know, the club managed to sign defenseman Chris Tanev to a six-year, $27 million contract and Oliver Ekman-Larsson to a four-year, $14 million deal.

    The pair headlined the Leafs’ most notable moves as the beginning of free agency has come and gone, but the two were not the only key targets the club had a prime interest in on July 1. As mentioned by TSN insider Chris Johnston on Tuesday’s SDPN Podcast, while fielding calls on Brady Skjei and Brett Pesce, who signed with the Nashville Predators and New Jersey Devils respectively, the Leafs had significant ambitions to land Matt Roy. 

    “I think Matt Roy was a little bit of the one that got away. They were interested in Brady Skjei but that was pretty clear early on that, that wasn’t going to be it,” said Johnston. “They called on Pesce, but I didn’t get a sense that was ever [close]. Roy was a big target.”

    [embed]https://www.youtube.com/watch?v=uo2kOqPWqkA[/embed]

    Roy, who completed a three-year, $9.45 million contract with the Los Angeles Kings at the conclusion of the 2023-24 season, earned a lucrative six-year, $34.5 million deal with the Washington Capitals as NHL free agency opened up – slipping through the Maple Leafs' grasp. 

    With Joel Edmundson, Ilya Lyubushkin, and T.J. Brodie among the notable unrestricted free agents on the club’s backend who could have left the organization come July 1, the Leafs were looking to shore up their defensive corps and improve their top four, preferably on the right side.

    As a right-handed shot and just 29 years of age, Roy fit the mold. He was coming off a career-high in assists (20) while adding five goals in his sixth season with the Los Angeles Kings. Posing as a great fit on the club’s second pairing, he had experience alongside Vladislav Gavrikov whom he played with in the same role in L.A., bringing a physical brand of hockey with reliable penalty-killing abilities as a solid two-way defenseman. 

    Roy's impending free agency clearly drew attention from multiple teams, including the Capitals, who eventually swooped in with a substantial offer. Despite Toronto's earnest pursuit, the deal with Roy never materialized, leaving management to reassess their options while locking down Tanev, Ekman-Larsson, and Jani Hakanpaa (although still not officially announced) to multi-year deals. 

    Still, these additions are viewed as sizable upgrades for the Maple Leafs, who managed to fill out their blueline despite falling short on a deal with Roy.

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