What if the Islanders had never sent Zdeno Chara to Ottawa in the Alexei Yashin deal?
That one move still hangs over both franchises, because it wasn’t just a swap of star names. The Senators got Yashin, while the Islanders landed Chara, Bill Muckalt, and the second overall pick, which became Jason Spezza. In hindsight, it looks like the kind of trade that could have bent the future for years.
The strange part is that Ottawa was never going to keep Yashin forever. He wanted out, and not quietly.
He asked to be traded three times in seven years, with two contract disputes mixed in along the way. So even if the Senators had turned down the Islanders’ offer, the breakup likely would have come later.
The real question is whether they ever could have done better than Chara and Spezza.
Probably not, especially because Mike Milbury was the GM on the other side. His trade record was shaky, and this one ended up giving Ottawa a franchise defenseman and a future No. 1 center. Yashin certainly mattered to the roster, but that doesn’t make it easy to justify giving up a top-pairing blue liner and a player who became a centerpiece down the middle.
For the Islanders, the alternate version of this story starts with the blue line. They already had Adrian Aucoin, Kenny Jonsson, and Roman Hamrlik.
Add Chara to that group, and suddenly you’re talking about one of the league’s best top fours for years. Dick Tarnstrom and Radek Martinek would have slid into the third pair, with Eric Cairns as the seventh defenseman.
That kind of defensive core could have been good enough to win a Stanley Cup.
And then there’s Spezza. Milbury wanted an upgrade at center, which is why he made the deal in the first place.
But he could have gotten that by simply taking Spezza with the second overall pick. Instead of Yashin, the Islanders would have had a younger center with a huge offensive ceiling.
Yashin was productive, putting up 290 points in 338 games, but Spezza’s Senators career was on another level: 687 points in 686 games.
Of course, that total might not have looked the same in an Islanders uniform. The surrounding cast would have been different.
But the bigger point is what that kind of player gives an organization: a chance to build differently, attract better free agents, and keep climbing. Years later, the Islanders added Bill Guerin, Doug Weight, and Miroslav Satan, and Jason Blake emerged as a top-six forward.
With Chara and Spezza already in place, that roster might have had a much higher ceiling.
That also raises the biggest what-if of all: would they still have ended up with John Tavares in the 2009 NHL Draft?
If the Islanders had kept Chara and drafted Spezza, the whole shape of the franchise might have changed. It’s not hard to imagine them as Cup contenders for much of the next decade.
In Other News...
Islanders Prospect System Suddenly Looks Better Than Anyone Expected
The Islanders prospect picture has taken a noticeable turn, and Scott Wheelers latest 2026 Top 100 NHL prospects list is a big reason why. Malte Gustafsson sits at No. 34 overall as the highest-ranked player in the organizations pipeline, a sign that the system is drawing far more respect than it did in recent years. New York also placed five players in Wheelers top 100, with Calum Ritchie, Victor Eklund, Kashawn Aitcheson and Cole Eiserman joining Gustafsson on the list.
For an organization that has spent plenty of time hearing about its shallow pipeline, that kind of representation matters. Ritchie, acquired from Colorado in the Brock Nelson trade, gives the group another high-end piece, while Eiserman remains one of the more intriguing names because his long-term value will depend on whether he can grow beyond being known mainly as a shooter. Wheelers rankings do not solve anything for the Islanders in the short term, but they do suggest the talent base is deeper and more interesting than it has been for a while. [Read more 🡒]
Canadiens Just Reignited The Noah Dobson Debate Islanders Fans Know Well
The Canadiens contract picture for 2026-27 has a familiar name sitting right in the middle of the debate for Islanders fans. Noah Dobson remains the kind of player whose value is easy to argue over because his deal and his usage invite the same question from two different angles: what a defenseman of his profile should cost, and how much he should be asked to do. For a player who once drew so much of his appeal from his role on the power play, the discussion around him in Montreal has become a useful reminder of how quickly the context around a defenseman can change.
Mike Matheson is part of that same conversation, and his situation only sharpens the contrast. His five-year extension has pushed him into more of a shutdown role, even as the offense has cooled, which is the sort of tradeoff teams live with when they believe the rest of the package still works. Josh Anderson and Phillip Danault also factor into the broader evaluation, but for Islanders readers, the real hook is the way Dobsons name keeps surfacing whenever Montreals roster math turns into a referendum on value, usage, and what a team thinks it is actually buying. [Read more 🡒]
Islanders Schedule Has A Few Dates Fans Will Circle Immediately
The Islanders 2026-27 schedule gives fans plenty to mark down before the puck even drops, starting with a Sept. 30 opener in Toronto and a home opener three days later against the Devils. From there, the calendar is packed with the usual Metro grind, including four meetings with the Rangers, plus a slate that mixes later start times, back-to-backs and the kind of road/home rhythm that can quietly shape a season long before spring arrives.
There are also a few dates that stand out for reasons beyond standings math, especially the first look at former captain Anders Lee and the games that come with it. Add in matchups against teams coached by Pete DeBoer, and the schedule has the feel of one that will keep Islanders fans checking the calendar as much as the box scores, with a handful of nights carrying a little more weight than the rest. [Read more 🡒]