Brendan Shanahan will not have his contract renewed as president and alternate governor of the Maple Leafs after more than 11 years in Toronto.

A tumultuous tenure has come to an end, leaving Shanahan without a job for the upcoming NHL regular season. Enter the Islanders, who were granted permission to speak with Shanahan prior to Thursday’s news.

The Islanders need a new president and general manager after announcing on April 22 that they were moving on from Lou Lamoriello. Their ongoing search has lasted a month and there is no immediate end is sight.

While Mathieu Darche and Marc Bergevin appear to be the current favorites to be hired as GM, it seems like the Islanders want someone with more experience to take Lamoriello’s old job.

Their search started with Ken Holland, who won four Stanley Cups while working for the Red Wings, but Holland was not interested. He accepted an offer to become GM of the Kings, an organization in much better shape than the Islanders.

Canadiens executive and former Rangers GM Jeff Gorton was also a top option for New York. Like Holland, the pursuit was unsuccessful, as Gorton had no desire to leave Montreal.

That is where Shanahan comes into play. If the Islanders don’t think Darche and Bergevin are ready to lead the front office on their own, Shanahan would provide the Islanders with an established, experienced president to guide the franchise into a new era.

However, Shanahan has some serious flaws. Let’s get the negatives out of the way.

Obviously, the optics of hiring Shanahan would be terrible.

A fanbase clamoring for meaningful change would be handed a tall glass of déjà vu. Seven years ago, the Islanders hired another former Toronto executive to lead their front office. At the time, the move was celebrated, but almost a decade later, the majority of Long Island wants nothing more than to rinse the taste of Lamoriello out of their mouth.

Shanahan would feel like a very similar hire, and this would upset a lot of fans. He worked closely with Lamoriello in Toronto, hiring the Hockey Hall of Famer as GM in 2015. The two were partners in crime for three years, launching a rebuild that led to a lot of regular season success, but very little postseason success.

Those postseason struggles are a big reason why Maple Leaf Sports and Entertainment decided to move on from Shanahan. In his 11 seasons leading the Maple Leafs, they won just two playoff series and never advanced to a conference final.

Under Shanahan, the Maple Leafs were eliminated in Game 7 six times (2018 vs. Bruins, 2019 vs. Bruins, 2021 vs. Canadiens, 2022 vs. Lightning, 2024 vs. Bruins and 2025 vs. Panthers). That does not include 2020, when the Maple Leafs lost a best-of-five qualifying series to the Blue Jackets in Game 5.

Quite simply, Shanahan and the Maple Leafs were losers. Their performance when it mattered most was pathetic, and one can argue Shanahan is at least partially to blame.

His emphasis on pure talent, skill and finesse was clearly not a recipe for postseason success. The Maple Leafs needed more heart, physicality and toughness, and Shanahan did not provide it.

Shanahan made some very questionable decisions during his time in Toronto. Of course, he was the president and alternate governor, not the GM, so he was not responsible for every single roster move. But as the man in charge, it is fair to blame him for the many bad decisions made under his watch.

Signing and then giving up a first-round pick to trade away Patrick Marleau was a monumental mistake. Letting Zach Hyman walk in free agency was quite costly. Trading Mason Marchment for Denis Malgin was bad. Dealing Nazem Kadri to the Avalanche was worse. And of course, his pursuit and signing of John Tavares and commitment to the “Core Four” was his biggest mistake, forming the foundation of a pyramid of issues and dysfunction in Toronto.

So with all of these negatives, why in the world would the Islanders hire Shanahan?

Well, he has experience turning a franchise around.

Shanahan joined the Maple Leafs after they missed the playoffs in eight of their previous nine seasons. He arrived in Toronto with a plan, which included drafting William Nylander, Mitch Marner and Auston Matthews and signing Tavares in free agency.

Matthews was taken with the first overall pick in 2016. Sound familiar? The Islanders currently have the first pick in the upcoming 2025 NHL Draft, and they need to hit a home run with their selection, like the Maple Leafs did with Matthews.

While the postseason success has not been there, Matthews helped the Maple Leafs win a ton of hockey games. They have made the playoffs in nine straight seasons (including 2020), good for the NHL’s longest streak of consecutive postseason appearances. They have averaged a points percentage of .639 since Matthews’ rookie season (2016-17). Their regular season record is 408-214-78 during that time.

The “Shanaplan” may not have led to the Stanley Cup, but the Maple Leafs have consistently been one of the best teams in hockey with Shanahan leading the way.

That means something.

So does Marner, a pending unrestricted free agent who is very familiar with Shanahan. After months of tense negotiations in 2019, Shanahan’s Maple Leafs signed the star forward to a six-year extension worth more than $65 million. Now, Shanahan could sign Marner once again, this time with a new team.

The Islanders have approximately $30 million in salary cap space heading into the offseason, meaning they could afford to sign Marner to the massive contract he will likely desire. Coming off an impressive season in which he recorded 27 goals, 75 assists and 102 points, the 28-year-old would be the most dynamic playmaker the Islanders have had in decades. He would likely benefit from a fresh start on Long Island, a market with much less pressure than Toronto.

Shanahan could provide the Islanders with a head start in the Marner sweepstakes, and that, combined with Marner’s friendship with Mathew Barzal and Matt Martin, may just be enough to push the Islanders across the finish line.

There are also some logistical reasons that could entice the Islanders to hire Shanahan.

Owner Scott Malkin, founder and chairman of SD Malkin Properties and European and Chinese outlet village developer Value Retail, is a busy man with a lot of obligations. He is frequently overseas and rarely seen around UBS Arena.

Hiring Shanahan would allow Malkin, who is well-known for having a hands-off ownership style, to focus on his business ventures while a trusted, capable man handles all things hockey operations — just like when Lamoriello was in charge.

Not to mention, John Collins, the operating partner of the Islanders, knows Shanahan quite well. Shanahan was the vice president of hockey and business development in the league office before getting promoted to senior vice president, working with Collins, the former NHL chief operating officer, for multiple years.

While the Islanders would have to pay up for Shanahan — he reportedly made $7 million per season with the Maple Leafs — he is someone both Malkin and Collins can feel comfortable with behind the wheel of the franchise going forward.

The ball is in Malkin’s court. Will he hire a GM first and then pursue Shanahan? Will Shanahan even want the job if a GM is already in place? Will he feel comfortable dishing out perhaps over $10 million a year for a new president and GM, when Lamoriello made much less?

All of these are questions the Islanders need to answer, and they need to do it fast. The draft is a month away and the Islanders cannot afford to mess it up.

While we don’t know who will be announcing the No. 1 pick, Shanahan is certainly an option. Fans may hate the idea, but if ownership loves it, that is all that matters.

Featured image of Brendan Shanahan courtesy of Nathan Denette/The Canadian Press

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