Islanders cautionary tale: 3 trade to move one really bad contract

On Friday, the New York Islanders did the unthinkable. They were able to successfully trade Andrew Ladd. And they did so without having to shed a first-round pick. Something that seemed like a pre-requisite just a few days ago.

Moving Ladd, who played five NHL games (including the playoffs) in 2019-20 and one AHL game for the Bridgeport Sound Tigers (the second-worst AHL squad) during the shortened 20-21 season, gave a cap-strapped Islanders squad a massive lifeline with $5.5 million in cap savings.

But that trade to Arizona on Friday doesn’t happen without two costly trades before it.

It took two trades to make a third for New York Islanders

The Andrew Ladd trade to Arizona also included a second-round pick in 2021, a second-round pick in 2022, and a conditional third in 2023. The condition on that third-rounder is if Ladd plays one NHL game in 2022-23 the Coyotes get the pick.

The Islanders are in no place to shed those assets to move Ladd if not for the Devon Toews trade last offseason and the Nick Leddy just a few days ago.

With the Toews and Leddy trades completed the Islanders had two second-round picks in 2021 and in 2022. Meaning they could easily move one in either year. As they did to ship Ladd to Arizona.

And that’s what happens with really bad contracts. It costs a lot to move them. And there’s no doubt that Ladd’s contract was one of if not the worst in the NHL.

Since that ill-advised $38.5 million singing in 2016, Ladd played 181 of a possible 370 NHL games with the Isles (49%) and scored 72 points, a 0.4 points-per-game pace over his Islander career (that’s a 33 point player basically).

Ladd was mainly used at the AHL level over the last two seasons where he played 35 games for the Bridgeport Sound Tigers.

He wasn’t good enough to play at the NHL level but was healthy enough to play so his $5.5 million contract (which was over 80% signing bonus) was unmovable. Basically tethering the Isles to $4.475 million in dead cap space since 2018-19.

Again, this is what happens when teams sign players to really bad contracts. It costs a lot to get out of them. And I’m not just talking about the three picks the Isles sent to the Coyotes, but the two trades it took to get those picks to move Ladd.

Of course, the Toews and Ladd trades were not a direct result of signing Ladd in 2016. But if not for their trades Ladd isn’t moved, so in a way, you have to look at their moves as necessary to create that $5.5 million cap space.

The Islanders didn’t want to move either Toews or Leddy. Both were valuable players for the team, but it was necessary to do so. The Islanders needed cap space and moving them allowed the Isles to create some.

That’s why signing free agents to big-money deals isn’t always a good idea. Not only does it rarely work out well (subscription required) but when it doesn’t it costs a lot to get out from it.