On Rebuilding, Part 6: The New York Islanders

Jonathan Willis
August 10 2012 05:36PM

Frequent commenter and guest contributor RexLibris' series on rebuilds continues with the New York Islanders.

New Orleans York is Sinking

What are the myths and storylines that we, as fans, tell ourselves when it comes to the horror show rebuild that is going on in Long Island?

  • “Wang has had too direct a role in the team and has hired idiots to run his team.”
  • “They are the worst case scenario of a rebuild.”
  • “The Islanders are the perfect example of infinibuild, constantly finishing in the bottom of the league and never climbing up despite repeated lottery picks.”
  • “They are the perfect example of why I don’t want my team to intentionally tank the season, like the Blue Jackets and Oilers, because it isn’t a guarantee of anything.”

That should pretty much sum up the Islanders, right?

This is a common refrain amongst many fans around the league. And to be honest, it is hard to make any argument that the Islanders appear to have a plan, or even that reason and sound judgment play any role in the team’s management decisions. I don’t think anyone would argue that Charles Wang has, despite saving the team from bankruptcy, been a disastrous owner for the franchise.

To begin, it might be best to quickly review how the Islanders got to where they are today.

Dysfunction On Ice

The team is a mess and frankly when I wrote to Kent about this Islanders article I was sorely tempted to simply submit “they are screwed up six ways from Sunday” and leave it at that.

Wang, along with business partner Sanjay Kumar, bought the team from Howard Milstein and then-part-owner of the Phoenix Coyotes Steven Gluckstern, in 2000. Apparently Gluckstern didn’t feel he was losing money quickly enough and wanted to diversify his liabilities. During the 1995-1996 season Mike Milbury was elevated by Milstein and Gluckstern to GM while retaining his position as head coach. The first thing that Wang did was to give Milbury complete freedom over the hockey operations. Funny thing, this turns out to have been a bad idea.

Milbury took over from Don Maloney, current GM of the recently resurgent Phoenix Coyotes that had once been partially owned by Maloney’s former boss in New York, Steven Gluckstern. Maloney was fired because he chose to take the team in a different direction. Maloney determined that the team was overachieving and that their level of accomplishment in their previous playoff series win in 1992-1993 (their most recent playoff series win) was unsustainable. Essentially, Maloney chose to rebuild the franchise because he could see that the team wasn’t very good. The fans revolted and the ownership fired him for it.

The Islanders spent much of the time from 1995 to 2008 attempting to cobble together a team and compete for the playoffs. That they didn’t, and in fact failed in a spectacular fashion in many seasons, speaks to the poor management of the team.

It’s Worse Than You Think

Contrary to popular belief, the Islanders haven’t been rebuilding for a decade. They have been rebuilding for nearly three decades. Since posting a 103 point season in 1983-84 the team has only ever posted a 90+ point season three times in a span of twenty-eight years. In that same time the team has posted a season with 60 points or fewer six times, although one of those years was the shortened lockout season of 1994-95 where they were on pace for 70 points, if that is any consolation.

In the past sixteen years (excluding this June’s draft) the Islanders have had fourteen top-ten draft picks. Nine of those have been in the top five with two of them being 1st overall selections (Rick DiPietro and John Tavares). Of the players drafted with those selections six are still with the organization, with one still in junior (Ryan Strome).

The remaining players drafted were all traded away in many of Milbury’s moves that resulted in greatly diminished returns.

For the sake of brevity, we’ll restrict our review of the team’s rebuilding process to the Garth Snow era following the lockout, 2006 to present.

A Look at Garth Snow

Snow retired as the Isles backup goaltender in order to accept Wang’s job offer as NHL GM. Wang had hired Neil Smith to run the team a short while earlier but fired him after just over a month. It was at this time that the infamous Rick DiPietro contract was offered, apparently under Wang’s guidance. Snow’s immediate moves could now be said to be a great improvement over Milbury when looking over two of his first trades with the Oilers. He acquired Ryan Smyth at the 2007 trade deadline for Robert Nilsson, Ryan O’Marra and the draft pick that was used to select Alex Plante. An argument could be made that six or eight weeks of Smyth was equal value to those three prospects as Nilsson has almost washed out of the KHL, O’Marra was traded between AHL teams and Plante has yet, nearly six years later, to land a regular NHL job. Snow’s next trade with the Oilers sent Allan Rourke and a 3rd round pick over in exchange for a 2nd round pick used to select Travis Hamonic. Things were looking up for the Islanders, if only they had kept trading with Edmonton.

Unfortunately for Isles fans, it seems that Snow began to catch whatever Milbury had.

In Garth Snow’s time as GM the Islanders have continued to alter and modify their draft order, occasionally trading back with obvious gains as in 2008 when they were able to trade down initially from 5th overall to 7th and then from 7th to 9th while selecting Josh Bailey and adding two additional 2nd round picks and a 3rd round pick. Snow did the opposite the following year when he traded his 1st, 2nd, 3rd and 4th round picks to Columbus for their 1st and 3rd round picks, then immediately sent those two draft picks and a 7th round pick to the Wild for their 1st round pick. In the end the Islanders sent away a 1st, a 2nd, a 3rd, and a 7th round pick to climb the draft order from 26th overall to 12th. The draft picks that they sent away were used to take players such as Matt Hackett, Nick Leddy, and Kyle Palmieri, while the Islanders selected with that improved draft pick Calvin de Haan.

The really curious part of the whole deal, on both sides of this exchange, is that the following day Columbus essentially reversed their earlier decision and traded the 3rd and 4th round picks they received the day before from the Islanders in exchange for a 2nd round pick. This amount of wheeling and dealing would leave even Dean Lombardi’s head spinning.

Whither the Isles?

The Islanders never appear to be trying to move in a sustained direction, be it up or down. At one draft they will stockpile picks, trading away players and prospects, while in the following year they will reverse this course and trade away draft picks or the prospects most recently acquired in exchange for NHL-ready players.

The consistency that the Islanders have had at the level of ownership and management hasn’t carried down the corporate food chain. Since 2006, the team has had four head coaches: Brad Shaw, Ted Nolan, Scott Gordon and Jack Capuano. This much changeover in coaching directions amongst a young core is likely to have a long-term deleterious effect on the team’s identity and their ability to “buy-in” to a coach’s message and strategy.

Interestingly enough, the Islanders have drafted relatively well, for all of the other areas of franchise incompetence. Garth Snow has committed to prioritizing the draft in the past few seasons and been generally reluctant to trade away valuable picks. His scouting staff appear to have rewarded that strategy with some of their selections. The same prioritizing of the development of those draft picks may be another matter and is somewhat outside the scope of what this inquiry can provide.

A brief look at the Isles recent daft draft history

The 2005 draft was entirely unspectacular for the Isles with Ryan O’Marra, selected 15th overall, being the most successful player selected (33 games player, 7 points). The following year the Islanders stocked up on draft picks, hoarding 13 selections, including four 4th round picks. Unfortunately, Kyle Okposo and defenseman Andrew Macdonald are the only two who have turned into NHL players out of that group.

The following year Snow appears to have de-emphasized the draft, having only five picks, beginning in the 3rd round. From that year only Mark Katic has had any time in the NHL (11 games, 1 point). This was the year that Snow traded for Ryan Smyth and it appears that the team was under pressure to make the playoffs, which they did, although they were eliminated in the first round.

In 2008 Snow again hoarded picks to the tune of thirteen selections. Nine of those thirteen have played at least one game in the NHL with Travis Hamonic, Josh Bailey, Jared Spurgeon and Matt Martin being the headliners from that year.

2009 and 2010 were quieter years at the draft podium with fewer picks, but arguably more productive, as the Islanders added John Tavares, Calvin de Haan, Anders Nilsson and Casey Cizikas in 2009 and then Nino Niederreiter, Brock Nelson, and Kirill Kabanov the following year.

Last year the Islanders added to their already strong center prospect group with Ryan Strome while this June they hold the fourth overall selection and may have the opportunity to add one of a top-flight defensive prospect, a center, or a power-forward winger.

The amateur draft hasn’t been as much of a problem for the organization as what management has chosen to do with those prospects afterwards.

Not Right in the Head

It is difficult to discern the reasons for the Islanders seemingly being a perpetually poor team without resorting to oversimplified statements like “management are all idiots” and “ownership has screwed things up so badly nobody could make that group successful”. Suffice to say the team has spent longer being irrelevant than it ever did being relevant in the NHL.

The Islanders ought to have in place the pieces necessary to compete, or at least not embarrass themselves, every season. As in many things, there are a multitude of reasons why the Isles seem to always be at the top of the draft order.

First and perhaps foremost is the performance and impact that their starting (and I use that word loosely) goaltender has provided to the team. The DiPietro contract could make Freddy Krueger wake up in a cold sweat. DiPietro cannot seem to remain healthy for more than a dozen games at a time and since breaking into the league in 2005-2006 has played a career high of 63 games (2007-2008) while over the last four seasons has never played more than 26 games at any professional level. In fact from 2008 to 2012 he has played 5, 8, 26 and 8 games in each season, respectively. His cap hit is $4.5 million a season until 2021. Recently drafted Ryan Nugent-Hopkins will be 28 years old (and perhaps even starting to shave) when that contract expires. If an amnesty clause is included in the next CBA it ought not be nicknamed after Scott Gomez, or even Matt Stajan or Shawn Horcoff, but Rick DiPietro.

However, the truly frightening aspect of the Islanders, as it relates to DiPietro contract, is that the team has actually been reliant on that contract in order to buoy it above the salary floor. Maintaining a poor team can be excused for one of two reasons: financial restrictions or an unwillingness to overpay free agents who would only falsely inflate a team’s performance and inhibit draft ranking when rebuilding with intent. The Islanders appear to be trying to do both.

Charles In Charge

This leads us directly into the next aspect of the Islanders’ poor performance: ownership. It was Wang who led the negotiations for the DiPietro contract following the resignation of Milbury and the hiring of Garth Snow. Wang’s moves have seemed almost counter-indicative, at one moment signing players to expensive, long-term contracts such as the DiPietro and Yashin contracts, then instructing Snow to operate a franchise in the salary-cap cellar.

Wang’s preferred style of management is by committee and in his other business dealings terms have been used such as “heartless” and “abusive”. Apparently it was this operate-by-committee approach that resulted in Neil Smith’s being released so quickly after his initial hiring, as he felt he needed to run every single move past a collection of individuals including Wang and several “non-hockey” consultants.

It deserves mention that Wang has had several class-action suits leveled against him for his part in the running of Computer Associates and some accounting discrepancies that resulted in his being paid out nearly $700 million. To that end, financial restrictions, coupled with the limitations of playing in one of the NHL’s oldest arenas, are, in my opinion, playing a significant role in Wang’s running the team at or near the salary floor. The financial restrictions alluded to earlier would seem to have some bearing in the team’s consistently low payroll.

They have tried several creative approaches to make up for this lost revenue.

Be that as it may, I don’t believe that Wang is especially interested in retaining his ownership of the team, and has in fact come out and said that he regrets purchasing it. It is likely that at this point he is focusing his efforts on leveraging the value of the team to optimize his Lighthouse land development project, essentially using the franchise as a kind of collateral against a real estate deal.


The Islanders are often described as being in a perpetual rebuild, and this criticism isn’t entirely without merit. While they have a stable full of very talented young players that any other team in the league would love to poach, there appears to be little direction or method in the approach (are you sensing a theme here?).

I would argue that the Islanders are in the most desperate need of new ownership and a slightly different kind of rebuilding effort. The concept of a scorched-earth approach needs to be applied to this organization, though not in the player ranks. The ownership, management and some personnel positions of this franchise need to be expunged. A rebuild is necessary, not in the player or even the scouting ranks, but amongst the group of individuals who hold the majority of the responsibility for the absolute disaster and embarrassment that the New York Islanders have become.

Don Maloney attempted to do the right thing in the past, by drafting high and leveraging assets to acquire elite players at key positions. His removal at the angry demands of the fans only resulted in the rebuild being delayed. Unfortunately the person eventually hired to oversee this process was Mad Mike Milbury, a nickname that Milbury first used when referring to himself in the third person after defending his selection of Rick DiPietro 1st overall. A pick he obtained by trading away the recently-drafted Roberto Luongo.

Since embarking on their second rebuild of the modern era, their first being under Maloney at the beginning of the millennium, one half of the organization has been doing things by the traditional rebuilding book: using high draft picks to succeed in finding a good player at that position. There haven’t been many 1st round busts since Garth Snow took over: Okposo (7th), Bailey (9th), Tavares (1st), de Haan (12th), Niederreiter (5th), Nelson (30th), and Strome (5th). At the same time, the fact that the team has had eleven top-five picks in the past seventeen years speaks to a deeper malaise within the organization and takes us to the other half of the franchise that is horribly underperforming. Unfortunately, the lackluster half is that which reviews and supervises those on the other side of the coin, removing those that it deems not to be living up to expectations while avoiding the same fate for themselves.

So, to review, our myths surrounding the Islanders:

  • They have been rebuilding for the last ten years - This is false. They have been rebuilding, on and off, for nearly thirty years with a few short exceptions when ownership interfered and demanded an instantaneous winner, resulting in the addition of an Alexei Yashin. To put it in the good doctor’s words: “It’s worse than that. He’s dead, Jim.”
  • Charles Wang bears a great deal of responsibility for his meddling management style - From what can be learned at a distance this would appear to be true. Wang prefers a management-by-committee style. Basically, no argument here.
  • Charles Wang has employed idiots, amateurs and madmen to run his business almost to flaunt his disregard for the franchise in front of the fans who are held emotionally hostage - It’s hard to argue with such a heartfelt statement, but at the same time it has just enough truth to it that it doesn’t sound entirely unreasonable. Wang has a very difficult reputation in the business world, one not synonymous with the term “team”. It is often said that a person doesn’t make enough money to buy a hockey team by employing stupid people, and yet there are endless examples of owners making poor hiring decisions for their sports teams. In the end, Wang made a poor choice in retaining Mike Milbury and while Garth Snow appears to be an improvement in that department, it is faint praise indeed.
  • The Islanders are the worst-case scenario of a rebuild and are an example of what the Oilers are going to become pretty soon with their perennial 30th place finishes - Putting aside my own emotional response, the Islanders are not a worst case scenario of a rebuild. They are a worst case scenario of a franchise. Period. Charles Wang, Mike Milbury and Garth Snow are the kinds of owners and managers that fans see in their darkest nightmares. As for the Oilers, while there are some historical ties that will always run between these two organizations and the state of their respective arenas bear some similarities, that is where the comparisons end. They have different owners, different management structures entirely, and the two franchises have been on very different paths over the past fifteen years. But I’ll spend more time on that when discussing the Oilers’ rebuild.
  • The Islanders are an example of how finishing at the bottom of the league and drafting high isn’t a guarantee of every improving, in fact it can mean spending the next twenty years at the bottom of the league -The Islanders do not represent a necessary outcome to a rebuilding strategy. They are one example amongst many and ought to serve only as that, one possible, and avoidable, outcome amongst all the others.

What derailed the Islanders’ initial rebuilds in the nineties was similar to what derailed the Flames Young Guns era. Financial constraints meant that drafted talents could not be retained. When the Islanders did find exceptional talent, it was traded away by incompetent management before the players could mature and contribute to the team. There are many great players that the Islanders selected, players who have made a mark on the league and have had long, productive careers in the NHL. Amongst Todd Bertuzzi, Bryan McCabe, Zdeno Chara, Roberto Luongo, Eric Brewer, Wade Redden, and Zigmund Palffy none of them were retained long enough to become impact players for the Islanders. Mike Milbury traded many of them before they could even develop into the kind of players that we would recognize today. In this regard, Milbury could be said to have been the best GM that the other 29 teams ever had. Trading with Milbury was like the free space on a bingo card.

In spite of being located in New York the Islanders were in many ways a small market team prior to the 2005-2006 lockout. Following their dynasty years the team gradually lost ground to the larger market teams that were able to outspend them. In a vain effort to revisit past glory the team kept trying to tread water and return to the playoffs, while ownership became more interested in withdrawing funds from the team’s revenue streams than reinvesting it. Every year since has more or less been cut from the same cloth, where ownership demands competitiveness while management attempts to throw together an NHL-worthy roster with a motley cast.

Don Maloney lost his job because he was unable to serve the two masters, the fans desire for success and ownership’s desire for a profitable product, without first leading the team through the valley of the shadow of death: bottom of the league/the top of the draft. In the end the team ended up there in spite of Milbury’s efforts.

Mike Milbury was given too much authority and afterwards was retained far too long. He eventually had the luxury of resigning and now, inexplicably, is given regular opportunities to espouse his thoughts on hockey in a public forum.

Garth Snow appears to be reversing some of this trend in that he has chosen to retain, for the most part, many of the talented young players that the Islanders have drafted. He has added depth players through the waiver wire in Michael Grabner and by unrestricted free agency in Matt Moulson and P.A. Parenteau. The Islanders remain an enigma of an NHL franchise, but their current rebuild needs to be weighed against its modern lifespan, est. 2006.

Previously in this series

Jonathan Willis is a freelance writer. He currently works for Oilers Nation, Sportsnet and Bleacher Report. He's co-written three books and worked for myriad websites, including the Edmonton Journal, Grantland, ESPN, The Score, and Hockey Prospectus. He was previously the founder and managing editor of Copper & Blue.