On Oct. 12, 2020, the fate of the New York Islanders changed forever when President and General Manager Lou Lamoriello traded Devon Toews to the Colorado Avalanche for a 2021 second-round pick and a 2022 second-round pick.

At the time, many believed this was a necessary decision. The Islanders had about $9 million in cap space during the 2020 NHL offseason with three important restricted free agents to re-sign (Mathew Barzal, Ryan Pulock and Toews). In a flat, $81.5 million salary cap partially caused by the COVID-19 pandemic, Lamoriello had a problem on his hands.

However, he took the easy way out and traded Toews, setting the franchise back immensely.

In the season after they traded Toews, the Islanders lost to the Tampa Bay Lightning in the Stanley Cup Semifinals for the second consecutive season — this time in Game 7 by only one goal. Toews could have made the difference.

Now, the Islanders’ defense is in shambles, with 44-year-old Zdeno Chara in Toews’ spot playing over 18 minutes per night. This all could have been avoided if Lamoriello found a way to keep Toews, who signed a four-year, $16.4 million extension with the Avalanche two weeks after the trade — now one of the best contracts in the NHL.

In this article, I am going to look back and discuss three things Lamoriello could have done to keep Toews. Yes, I have the benefit of hindsight, but these plans could have easily been implemented.

If they were, the Islanders would still have Toews — and potentially their fifth Stanley Cup, too.

Sign Leo Komarov To A Shorter Contract

The Islanders signed Leo Komarov to a four-year, $12 million contract on July 1, 2018. At the time, Komarov was a five-year NHL veteran with 52 goals, 70 assists and 122 points in 327 games, all with the Toronto Maple Leafs. Lamoriello clearly valued Komarov’s physicality — as of 2018, he never finished with under 200 hits in a season where he played at least 43 games — and his leadership.

Signing Komarov was not a bad idea. He was a gritty forward who Lamoriello correctly believed would help change the culture of the Islanders. The only issue was the term.

Komarov — now with SKA Saint Petersburg of the KHL — would have likely taken a shorter deal. The New York Rangers were one of the only other teams with serious interest, but Komarov’s connection with Lamoriello — who was the general manager of the Maple Leafs from 2015-2018 — was a main reason a deal with the Islanders was completed.

The New York Rangers have been in talks with forward Leo Komarov on a multi-year deal. Sounds like it’s getting to that point. Wouldn’t be surprised to see deal finalized on Sunday.

— David Pagnotta (@TheFourthPeriod) June 28, 2018

There was no reason to sign a 31-year-old to a four-year contract when a two- or three-year deal would have certainly gotten the job done. This would have allowed Lamoriello to have more long-term flexibility, potentially allowing the Islanders to sign Toews two offseasons later.

Trade Nick Leddy One Year Earlier

Nick Leddy was traded to the Detroit Red Wings for Richard Panik and a 2021 second-round pick on July 16, 2021. The defenseman had one season remaining on the seven-year, $38.5 million contract he signed with the Islanders on Feb. 24, 2015.

Lamoriello should have found a way to trade Leddy a year earlier.

Just two weeks before Toews was traded, the Red Wings acquired Marc Staal and a 2021 second-round pick from the Rangers for future considerations.

“For the Red Wings, we are in a position, we do have cap space that we can use,” Red Wings’ general manager Steve Yzerman said after the deal. “I hope to use it wisely, but one way we would like to try and use it is to acquire future assets should any teams be in a position where they really have to move contracts and don’t have any other options.”

Staal was coming off an 11-point season in 52 games for the Rangers. Leddy was coming off a 21-point season in 60 games for the Islanders.

If Lamoriello offered Leddy and a second-round pick to the Red Wings, they would have surely taken the deal. Leddy was a significantly better player than Staal at the time and the Red Wings clearly had interest in Leddy, considering they acquired him a year later.

Choosing Leddy over Toews — only to trade Leddy a year later — was a monumental mistake for Lamoriello, and it will be felt for years to come.

Get Creative

When the Tampa Bay Lightning needed to keep their core together after winning a Stanley Cup, they got creative. On Dec. 27, 2020, they traded Cedric Paquette, Braydon Coburn and a 2022 second-round pick to the Ottawa Senators for Anders Nilsson and Marian Gaborik, who both were placed on long-term injured reserve (LTIR). They thought outside the box, became salary cap compliant with one move and it led to another Stanley Cup.

The Islanders should have done something similar. They could have matched the Lightning’s offer and acquired Nilsson and Gaborik, or they could have taken a different approach. Perhaps, they could have acquired the final season of Marian Hossa’s $5.275 per year contract from the Arizona Coyotes and placed Hossa on LTIR. All it would have taken was a few draft picks and the Islanders could have solved their salary cap crisis.

When Lamoriello was with the Maple Leafs, he made the contracts of Stephane Robidas, Joffrey Lupul and Jared Cowen go away through LTIR. With the Islanders, he missed out on a golden opportunity, and paid the price by trading Toews.

David Lazar