Revisting Every Major Lou Lamoriello Transaction as the Islanders Ponder His Future

Last night, the New York Islanders saw their season come to an end. The team finished with their fewest wins and worst league-wide finish since the 2017-18 season, before Lou Lamoriello arrived and took over the ship.

The Islanders clinched their lowest finish in the standings since the 2017-18 season, the final year of the Garth Snow era. That Draft Lottery the Islanders entered holding the 10th and 12th overall picks (Calgary via Travis Hamonic trade).

The Draft Lottery is roughly two weeks away. The NHL Draft is in 70 days. Free Agency opens in 74 days. That might seem a long way away, but things will quickly start happening here. Right now, there’s one decision looming larger than all above the New York Islanders’ franchise: Team President and General Manager Lou Lamoriello’s future.

It’s expected he will remain in charge, but there’s more than a shadow of doubt that his future is endangered. Since June of 2021, the team has won three total playoff games over four years while doubling down on this core at every turn.

Lamoriello’s been in charge since the Spring of 2018, with major moves throughout his tenure. Let’s revisit every major move he’s made since coming aboard and evaluate the job he’s done.

The Early Highlights of Lou Lamoriello’s Tenure:

May 22, 2018. A day that changed the franchise forever. That day, the team hired Lou Lamoriello as the President of Hockey Operations. Less than two weeks later, he fired longtime GM Garth Snow, along with Head Coach Doug Weight, following consecutive playoff misses.

Within the month that followed, Lamoriello hired Stanley Cup Champion Barry Trotz to be the new head coach while John Tavares walked away from the franchise. Nobody could fill the void Tavares left, so Lamoriello needed to bring in locker room guys to stabilize the room. He signed beloved veterans Leo Komarov and Valtteri Filppula on July 1. He re-signed Thomas Hickey. On July 2, he traded for Matt Martin. On July 3, he signed Robin Lehner, who went on to win the Masterton Trophy, split the Jennings Trophy with Thomas Greiss, and became a Vezina finalist.

Those moves kicked off a magical 2018-19 season where the Islanders wildly outperformed expectations and gained home-ice advantage for a playoff series for the first time since 1988, something the team still has yet to do again. That year, they swept the Penguins before getting swept by the Carolina Hurricanes. Brock Nelson signed a long-term extension after breaking out under Trotz, one of the best contracts Lamoriello signed a player to. Nelson became a perennial 30-goal scorer on the relative cheap.

Lamoriello extended Jordan Eberle and replaced Lehner with Semyon Varlamov. He also brought in veteran Derick Brassard on a one-year deal.

In the two years that followed, COVID-19 hit. Just before that happened, Lamoriello landed a player at the top of the trade boards. Pageau arrived weeks before the world shutdown in 2020 and helped the bubble Islanders win three series before falling to the Lightning.

One year later, Anders Lee tore his ACL, ending his season. Lamoriello turned around and acquired Kyle Palmieri (and Travis Zajac), another highly valued piece. Beyond both acquisitions and despite missing Lee for the entire run, the Islanders came one game short of advancing to the 2021 Stanley Cup Final.

The Devon Toews Trade:

In that moment, June of 2021, the future seemed bright. The Islanders were on the precipice of the Cup, but fell just short. Beneath the surface, one fatal error had already taken place.

Let’s rewind a bit. In the cap-frozen world of 2020 and with an uncertain season ahead, nobody wanted to take on any contracts. The Islanders declined to investigate moving Nick Leddy. Before COVID-19, the team handed Pageau an extension based on the cap rising by a certain amount.

The Islanders found themselves in a squeeze when blossoming defenseman Devon Toews filed for arbitration. With no money free, the Islanders sent him to the Colorado Avalanche, where he signed a four-year deal, which turned into a new seven-year extension after that. He’s since become one of the best defensemen in the league, though some of that is aided by the privilege of playing with Cale Makar.

It’s a move the Islanders, presumably, would still like a mulligan on.

Summer of 2021:

One year later, the Islanders found themselves in another money bind. They needed to re-sign key RFAs, including Anthony Beauvillier and Ilya Sorokin, to raises. They had UFAs they wanted to keep, including Kyle Palmieri and Casey Cizikas

Right away, Lamoriello made moves. He dumped Nick Leddy to Detroit. He found a way to move Andrew Ladd’s remaining contract to the Arizona Coyotes. After that, he had an opportunity. The Seattle Kraken were entering the league and had literally all of their cap space at their disposal. The Islanders left Jordan Eberle and Josh Bailey, with their $5 million cap hits, exposed. Seattle took Eberle. 

Lamoriello replaced Eberle by paying his exact salary hit to Palmieri on a new four-year deal. Eberle initially outproduced Palmieri in 21-222 and 22-23. Since then, Palmieri’s outproduced Eberle by a wide margin. Palmieri has 54 goals in his last two seasons with no injuries. Eberle has just 26 and missed half this season due to injury.

Lamoriello made the right call, and Palmieri over Eberle long-term has proven correct.

With Leddy and Eberle departing, the Islanders made no major moves. The team hoped Oliver Wahlstrom could step up while they signed Zach Parise.

Defensively, for a second straight offseason, the team moved a mobile defender without bringing another in. Yes, the young Noah Dobson began to step up, but he alone could not fill the void yet. The team signed Zdeno Chara and re-signed Andy Greene. It wouldn’t work out.

The 2022 Offseason:

After the 2021 offseason, the Islanders entered 2021-22 as a Stanley Cup favorite. Instead, they collapsed. Starting with a 13-game road trip that lasted over a month due to UBS Arena not being ready for an October opening, the team got off to a slow start and never recovered.

Heck, the night the building opened, half the team had COVID-19 or were injured. The team limped to a playoff miss and earned the 13th Overall Pick in the 2022 NHL Draft.

After discussions with Barry Trotz over an extension failed and after player meetings with Lamoriello provided feedback, Lamoriello dumped Trotz in a shock to the hockey world. He promoted Lane Lambert to head coach, who was rumored to leave the organization for another head coaching gig that summer.

Instead, the Islanders gave Trotz the boot and promoted Lambert. Lamoriello fired assistant coaches John Gruden and Jim Hiller, the latter of whom became the Los Angeles Kings Head Coach.

Transactionally, the only major move came by way of acquiring Alexander Romanov for that 13th Overall Pick (Frank Nazar) in a three-team trade with the Montreal Canadiens and Chicago Blackhawks.

The only effective summer signing came by way of Hudson Fasching, signed as an AHL pick-up spearheaded by Chris Lamoriello, Bridgeport’s GM. Mathew Barzal signed a massive eight-year extension at the start of training camp.

2022-23 and July 1, 2023:

Lambert could not capture Trotz’s abilities. The team struggled out of the gate in the 22-23, but were very much in the playoff race, but lacked a big-time goalscorer.

Lamoriello stepped up. In January of 2023, with the team struggling again, Lamoriello bet on the core swung big and landed the top trade piece available in Bo Horvat. Horvat resuscitated life into the squad, and even after a Mathew Barzal injury, Horvat helped the Islanders make the playoffs in 2023. In those playoffs, the Hurricanes beat the Islanders in a hard-fought six-game series.

Even with Horvat, the Islanders had an opportunity to move pending UFA defenseman Scott Mayfield for upwards of a first-round pick at the 2023 deadline, but opted to hold onto all of their pending UFAs for the stretch run, which resulted in a playoff berth.

After the season, Lamoriello dumped Josh Bailey on the Chicago Blackhawks, who bought out Bailey. Bailey retired after getting cut from the Ottawa Senators that fall.

With some more cap space and more players needing raises, along came July 1, 2023. Lamoriello’s biggest bet on this core yet. Pierre Engvall, acquired at that deadline, seemed to fit right in. Most forecasted a modest extension. Lamoriello signed him to a seven-year deal. Scott Mayfield, one of the top free-agent defensemen, stayed home on an equally large seven-year deal. Semyon Varlamov signed a brand new four-year deal.

Ilya Sorokin also signed an eight-year extension that would kick in the following summer. At that moment, July 1 of 2023, nine players on the Islanders’ roster were on contracts lasting until 2027 or later. Those long-term deals joined the ranks with Adam Pelech, Ryan Pulock, Barzal, & Horvat’s long-term deals on the books until 2029 or later.

2023-24:

With those moves, Lamoriello directly tied his legacy to that of his core. After his first four years in charge showed a ruthless streak, he became too attached to the current roster.

The 2023-24 season brought very little change. Simon Holmstrom began to show flashes and played over 70 games. Elsewhere, the roster stayed essentially the same. Thanks to injuries, Mike Reilly arrived via waivers while the team acquired Robert Bortuzzo from the St. Louis Blues for a conditional draft pick.

The biggest move came via Lane Lambert continuing to be outmatched and getting fired midway through the year. The third coach of the Lamoriello regime became Patrick Roy, whose own track record is a mixed bag we evaluated a few weeks ago.

That team lost in a swift five-game series to the Hurricanes, the third time Carolina has eliminated Lamoriello’s Islanders since he was hired.

2024-25:

The Summer of 2024 saw two more additions to the forward group: Anthony Duclair and Maxim Tsyplakov. Engvall, signed to a seven-year deal just 15 months prior, was cut from the opening roster.

Duclair has not worked out as planned. He tore his groin five games into the season, missed 28 games, and returned a shell of himself. Roy then publicly humiliated his player, who took a leave of absence for the remainder of the season.

Those two aside, the roster has not had any major changes. Thanks to injuries, Adam Boqvist arrived via waivers. Tony DeAngelo signed a one-year deal while the team acquired Scott Perunovich from the St. Louis Blues for a conditional draft choice. Bridgeport call-up Marc Gatcomb earned a role in the lineup with his strong play and will retain his spot for next season.

Barzal suffered two major injuries and missed 52 games, the most fatal blow for the season.

In terms of roster construction, nothing changed until this trade deadline, when Lamoriello admitted this isn’t working. He traded Brock Nelson to the Colorado Avalanche for a big return, signaling the start of a retool in a seller’s market. Instead, Lamoriello backed down and kept Palmieri, Pageau, and Lee. 

Lamoriello then publicly said he wanted to keep Nelson, but failed to come to terms, so he dealt him. Then, he publicly vowed change and said the team needs to get younger while refusing to bottom out. Palmieri, 34, may or may not have an extension done. The offers at the deadline for Palmieri amounted to second-round picks and mediocre prospects. Pageau and Lee needed money to be retained, something Lamoriello would not do.

The Islanders fought but ultimately limped and took lumps down the stretch, failing to make the playoffs. Lamoriello’s future is now the #1 question for the Islanders ahead of a summer where big moves are the priority.

The Bridesmaid for Big Moves:

Clearly, despite his reputation, Lamoriello made moves. Plenty of them. What you’ve read to this point is a retelling of his seven years in charge thus far. What that history did not include is the trend of falling short of adding a game-breaking forward or becoming the bridesmaid for a major move.

Let’s first rewind to 2019. After the team started red-hot, Lamoriello wanted reinforcements to help the squad. League insiders reported that the Islanders hunted after Matt Duchene and Mark Stone, the big fish at that deadline. Duchene headed to Columbus, while Stone ultimately landed with the Vegas Golden Knights.

That summer, Lamoriello’s quest for the big fish continued. It became widely reported that the Islanders went all-in on Artemi Panarin. Panarin, 27 at the time, remains the best free agent to hit the market since Tavares the year before. The Islanders even seemed to be landing him, too.

On June 30, Bob McKenzie tweeted the Islanders were the favorite to land Panarin alongside Semyon Varlamov. Less than 24 hours later, Panarin took the LIRR to Manhattan and never looked back.

After landing two bigger fish in 2020 and 2021 (Pageau/Palmieri), Lamoriello loaded up for 2022. The Islanders needed a difference-making forward, and at the 2022 NHL Draft, the Islanders seemed to have a deal in place with the Vancouver Canucks for J.T. Miller. The trade wound up falling through, and the Islanders pivoted to acquire Romanov.

During that upcoming summer, everyone knew the Islanders needed a top-line forward. Nazem Kadri became the target in free agency. The Islanders reportedly had a deal with Kadri, but needed to clear more salary. They failed to do so, and Kadri signed in Calgary.

In July of 2023, the Islanders allegedly went for Johnny Gaudreau, but Gaudreau himself debunked those rumors.

Most recently, Lamoriello tried to acquire names like Alex DeBrincat and Nikolaj Ehlers, but fell short of doing so.

Where Things Stand Now:

The Islanders need a major reset. One of Pelech, Pulock, or Mayfield has to be traded. With Calum Ritchie on the way and Roy expressing a desire to have Barzal at center, Pageau is extremely expendable. Engvall, despite a strong end to the season, should be bought out.

If his track record is any indication, Lamoriello, since July 1, 2023, may not be the man to do it. At the trade deadline, he said he knows there needs to be change, but readily admitted if he could have, his first choice was to keep Nelson.

If Lamoriello remains in charge as expected, this summer will define his legacy with the fan base. He’s the man who brought them from an all-time low to highs this franchise hadn’t seen since the 1980s. Lamoriello’s also the man who has repeatedly doubled down on an aging core that hasn’t yielded any fruit since 2021.

He’s brought in pieces for the future (Holmstrom, Ritchie, Tsyplakov, Eiserman) while building a strong nucleus (Barzal, Sorokin, Horvat, Dobson, Romanov). There’s enough there to build a contender. Aside from a freak jaw injury, Pelech remained healthy and had his best season since 2021-22 while having excellent underlying numbers.

Pulock and Mayfield also suffered injuries and took steps backward. Pulock battled back from an upper-body injury that took him out for a month. The injury stayed with him, and he played through lingering effects for the entirety of March and April, which heavily affected his play. Mayfield spent spells as a healthy scratch and seems the likeliest to be moved, whether by a buyout or a trade. He holds a full no-trade clause, complicating things.

In terms of RFAs, Dobson, Romanov, Holmstrom, and Tsyplakov all need new deals. All should be back for next season, even after all four had weak moments throughout the season. Both Romanov and Dobson battled injuries and played through things that impacted their effectiveness. As for Bridgeport, change is needed there too.

Armed with $28.9 million in cap space before any moves are made, now’s the time to retool and transform the team.

Islanders ownership, headed by Scott Malkin, must decide if Lou Lamoriello is the man to do it.