The New York Islanders have not been able to sign free agents and there's a few reasons why.

Since general manager Lou Lamoriello brought structure and respect back to the New York Islanders upon his arrival in 2018, he's had no issues with retaining players, whether already rostered or acquired via trade. 

Now, overpaying helps, and one could argue that the Islanders have had to overpay to keep players, but that's par for the course.

After standing pat at his first trade deadline with Long Island in 2019, he brought in Jean-Gabriel Pageau in 2020, signing him to a six-year deal worth $30 million upon arrival.

Prior to the 2021 NHL Trade Deadline, Kyle Palmieri was brought in. He signed a four-year extension worth $20 million before the start of the 2021-22 season. 

After standing pat in 2022, Lamoriello acquired star Bo Horvat before last year's deadline, inking him to an eight-year, $68 million deal before he even stepped foot on the practice ice. 

"When I got traded to the Island, I saw the facilities, the people, the organization, and everyone spoke so highly of it. When they offered me that contract, it was kind of a no-brainer, and thankfully we couldn't be more happy to be there," Horvat said during an interview with TSN radio earlier this week. 

Then Lamoriello traded for Pierre Engvall, who signed a seven-year deal worth $21 million on July 1st. 

But bringing in free agents has been much different and more challenging. 

The Islanders have swung and missed -- if you believe they've stepped in the batter's box -- seeing top-flight players choose anywhere but Long Island.

Given their roles with the Islanders, the two "biggest" free agent signings as of late have been Zach Parise at league minimum ($750K) in the summer of 2021 and Hudson Fasching last summer at $775K.  

For a long time, the Islanders were a mediocre hockey club playing in a worn-down Nassau Coliseum or a not-built-for-hockey arena in Brooklyn, which undoubtedly played a part in free agents looking anywhere but Long Island. 

But after finally finding a stable home at Belmont, a beautiful first-class sports arena, along with having a gorgeous practice facility in East Meadow, and a team that has made it to the postseason four of the last five seasons, many find it odd that the Islanders continue not to be a free agent destination. 

It's clear as day once players come to Long Island, they never want to leave. 

What are the reasons for failing to get free agents to come?

Not Having Cap Space

The free agency period is all about salary cap space. Many teams are dealing with the effects of the flat cap, which is why we saw many players take one-year deals to become free agents again next summer when the cap rises to a projected $87.7 million (currently at $83.5 M).

The Islanders have been salary-cap strapped for a few seasons now, and the pandemic didn't help their case at all. Not only were their contracts hindering their ability to make moves -- Lamoriello sharing in Nashville that they wouldn't have signed some if they knew the cap would not rise as expected -- but it was also rather impossible to move contracts without giving up top draft picks. 

Lamoriello had no choice but to move on from Josh Bailey and his $5 million cap hit this summer, paying a 2026 second-rounder to the Chicago Blackhawks for "future considerations" ahead of Day 2 of the NHL Draft.

READ MORE: Islanders Deal Bailey to Blackhawks

The Islanders did have cap space after moving Bailey, but Lamoriello chose to retain his own players with the money he had.

In the summer of 2022, the Islanders didn't have the funds to be prime players in the Johnny Gaudreau sweepstakes and failed to clear enough space despite extensive talks with Nazem Kadri and his camp. 

If you don't have cap space, free agents will go to teams that do. That part is not rocket science.

Long Island Taxes

We cannot discuss Long Island and a lack of free-agent success without discussing New York taxes.

While only nine states don't have an income tax -- Florida, Texas, and Texas are the only three states that have NHL franchises -- New York has the highest tax burden of any state, at 12.47 percent. 

"But these athletes make so much money."

Per a 2019-20 Statista report, the NHL owned the seventh-highest average salary amongst sports leagues, with an average salary of $2.69 million.

In 2022-23, the average NHL salary is $3.5 million.

So, compared to other sports leagues, NHL players aren't making as much, and then you have to consider New York athletes.

"But the Yankees have no issues signing players, so..."

Well, baseball doesn't have a salary cap (mic drop). They do have a luxury tax, but that doesn't stop the Yankees, nor should it.  

Outside of the MLB, other sports leagues like the NBA and NFL know how to market their players and teams more efficiently than the NHL. 

What's the income disparity between New York athletes in the NHL compared to athletes in other cities?

Let's focus on Islanders forward Mathew Barzal, who signed an eight-year extension worth $9.15 million annually, a deal that kicks in this upcoming season.

After paying taxes, an estimated effective tax rate of 50.35 percent, Barzal's net income is $4.54 million, and that's before paying his agent J.P. Barry around three to five percent ($227,000 if 5 percent). 

That means, before other expenses, Barzal is bringing home $4.3 million, around 47 percent of the money he signed for. 

And that's before he pays his property taxes and things like that. 

Again, still not a bad living to be an NHL player, but that's what happens when you live in New York.

Now, let's dive into Colorado Avalanche forward Mikko Rantanen, who makes $9.25 million annually.

After taxes, an estimated 46.98 percent in Colorado, Rantanen has a net income of $5,036,957. After paying agent Andy Scott (251,847 if 5 percent), Rantanen brings him $4.785 million, around 51.72 percent of his initial signing salary. 

This is why the Islanders tend to overpay players they bring in because life is just more expensive on the island. 

One of my followers Dayton Allderige messaged me the other day about this topic, which gave me the idea to dive into the tax breakdowns. He wondered if we could see the NHL add a tax penalty to teams that don't have a state income tax to be on the same playing field as high-tax states such as New York.

It's an interesting debate for sure, as it would certainly even the playing field, but I don't see it ever coming to fruition. 

That's why it's important for certain teams, like the Islanders, to handle their salary cap a bit differently than other markets. 

Lou Lamoriello

There's one final part that must be discussed, and that's Lamoriello.

Whether it's the shaving rule, having low numbers, curfews, or things of that nature, Lamoriello runs a tight ship, and it's certainly not suited for everyone. But from the mouths of players, past and present, people love playing for Lou, so I don't think that's as big of a deal as many may think.

It would be more of a story if the Islanders had the money and were putting up offers on free agents much higher than everyone else, and then those players were still choosing to go somewhere else. 

We must also remember the style the Islanders play, a defensive system that may rub creative players the wrong way, limiting what they can do on the ice. 

Lamoriello, who has always built his teams from goal on out, hired Barry Trotz upon his arrival, who brought about the defensive style the Islanders are still playing despite Trotz now general manager of the Nashville Predators. 

While effective in the postseason, the style is a grind, and not every player is cut out for that kind of game. 

What would truly entice NHLers to come to Long Island would be if they became a powerhouse in the NHL. But right now, that's not the case, and the Islanders will likely have to focus more on developing their own prospects.

Join Stefen Rosner's New York Islanders page on Bunches, a new app that connects sports fans. Also, you can listen to Rosner talk Islanders hockey on Hockey Night in New York with co-host Sean Cuthbert Sunday nights at 8 PM ET during the season.