Top 10 Worst Mike Milbury Trades, Contracts, and Transactions

worst Mike Milbury tradesMany might remember Mike Milbury as the hockey player who jumped into the MSG stands and beat a fan with his own shoe. Others might remember Milbury for his many controversies on and off the ice, but New York Islanders fans are imprinted with other not-so-fond memories of their former GM and coach.

Even though Milbury, Charles Wang, and Sanjay Kumar helped the Islanders get back to the playoffs in the early 2000s, the various transactions that Milbury made as the GM of the Isles had some long-term effects on the organization.

Here’s a look at some of Mad Mike Milbury‘s (worst) transactions from the late-90s to the mid-2000s:

10.) Traded Tommy Salo for Mats Lindgren & 8th Round Selection (Radek Martinek) – Tommy Salo turned out to be a solid goalie for the Oilers, but the Swedish netminder was showing signs of promise before Mike Milbury traded him. Milbury and Salo had a fractured relationship as Mad Mike assaulted Salo’s character during the goalie’s arbitration hearing and managed to make Salo cry during the processions.

However, Salo had the last laugh as he enjoyed a steady career with the Oilers and the players that he was traded for never really panned out for the Isles. Mats Lindgren was expected to be a good NHL talent but was hampered by injuries and never reached the potential that he was billed for. On the other hand, Radek Martinek turned out to be quite a find for an 8th round selection, but the defenseman was never able to stay healthy for a full NHL season and spent parts of every season on the IR.

bad Mike Milbury trades

(Icon SMI)

9.) Traded Brad Isbister & Raffi Torres for Janne Niinimaa – Milbury’s wheeling and dealing at the 2003 NHL Trade Deadline wound up costing the Islanders a good grinding winger. Raffi Torres never scored a goal for the Islanders, but wound up having 222 points (122 Goals, 100 Assists) in 545 games for 5 other teams. Torres’ frequent shuffling between teams and his high draft position (#5 Overall in 2000) indicate that the winger didn’t quite live up to his billing, but Torres’ physical style of play could have been utilized by the Islanders.

On the other hand, Niinimaa never met expectations on Long Island. As a defenseman that had tallied 30 or more points in five out of his first 6 seasons in the NHL, the trade could have looked good on paper, but it turned out to be anything but good for the Isles. In 136 games for New York, Niinimaa recorded only 44 points, an overall point total that he had accomplished four times (1996-1997, 1997-1998, 2000-2001, 2001-2002) while playing for the Flyers and Oilers.

At the time, Niinimaa looked like the solid route for Milbury as the d-man recorded more than 30 combined points for the Islanders and Oilers in 2002-2003. However, after recording 28 points in 82 games in 2003-2004, Niinimaa’s career in the NHL spiraled downward as Raffi Torres’ trended upwards. Raffi Torres was only given 31 games to show off his skills and impatience on Milbury’s behalf helped the Islanders rid themselves of a hard working forward.

Chris Osgood Stanley Cup finals

(Dustin Bradford/Icon SMI)

8.) Traded Chris Osgood & 3rd Round Selection (2003) to St. Louis Blues for Justin Papineau and 2nd Round Selection (Jeremy Colliton) – Chris Osgood was a fan favorite in Long Island and Milbury’s impatience with the goalie proved to be another great blunder. Osgood was having a sub-par season with the Islanders in 2002-2003, but the goalie managed to bounce back in 2003-2004 and even had two post-season appearances with the Blues.

Justin Papineau spent time shuffling back and forth between the Bridgeport Sound Tigers of the AHL and the New York Islanders, but he never developed into anything solid for the Isles. Some have argued that the bigger piece in the Osgood trade was the second round selection that turned out to be Jeremy Colliton, but to date the center has had a whopping 3 goals and 3 assists for New York in 57 games. Neither Papineau nor Colliton have had any sort of impact on the Islanders, but Chris Osgood wound up making several more postseason appearances and even won the Stanley Cup after being traded by Mad Mike.

7.) Traded J.P Dumont & 5th Round Selection (1998) for Dmitri Nabokov – Jean-Pierre Dumont went on to have a great and lengthy career with Chicago, Buffalo, and Nashville after Mike Milbury traded the right winger. Dumont had 5 seasons of 50 or more points for the Sabres and Predators while Dmitri Nabokov registered 13 points in 30 career games for the New York Islanders.

In Milbury’s defense, the New York Islanders were operating on a very meager payroll back in the late 90s, but to think that the Isles gave up Dumont and a 5th round pick for Nabokov is just absurd. A contract dispute forced Milbury to make a move, but a better suitor could’ve been found for this deal and Milbury should have netted a greater return than the bust that turned out to be Nabokov.

6.) Drafted Rick DiPietro with #1 Overall Pick at 2000 NHL Entry Draft – The New York Islanders turned heads during the 2000 NHL Draft, but for the wrong reason(s). Mike Milbury made hockey history when he selected a goalie (Rick DiPietro) with the number one overall pick at the NHL Entry Draft. The Islanders had been developing Roberto Luongo, but Milbury was convinced that DiPietro would be the future of the franchise.

DiPietro showed signs of promise during the early 2000s, but various injuries have limited the American-born netminder since 2007 and it is debatable if DP is any longer an NHL-caliber goalie. After appearing in 268 games from 2000-2008, DiPietro has appeared in 47 games from 2008 until the present day. Since 2008, DiPietro has only once been able to post a Save Percentage over .900 (.901 in 2009-2010) and his GAA has been in excess of 3.00 in three of the last four seasons.

Choosing Rick DiPietro with the number one overall pick had various ramifications for the New York Islanders in the late 2000s to the modern day. While DiPietro played on a couple of Islanders playoff teams, his injury woes and inability to live up to his long-term contract make him one of Milbury’s worst transactions. To add insult to injury, DiPietro was selected in front of prominent forwards such as Dany Heatley and Marian Gaborik. Both Gaborik and Heatley are having amazing NHL careers and Islanders fans are constantly left wondering what could have been if Milbury had drafted either forward with the first overall pick at the 2000 NHL Entry Draft.

(Flickr/Eric Colquhoun)

5.) Traded Bryan Berard & 6th Round Selection for Felix Potvin & 6th Round Selection – Bryan Berard won the Calder Trophy for the Islanders in 1997, but the defenseman wound up having some great years with the Blue Jackets, Blackhawks, Rangers, Maple Leafs, and Bruins.

Felix Potvin was not a bad return for Berard by any stretch as the goalie had enjoyed a very successful career with the Maple Leafs from 1992-1998. However, Potvin was not the solution in Long Island and the veteran’s numbers took a huge hit when he came to New York.

Since the Islanders operated on such a tiny payroll, it could have made sense for Milbury to get rid of Berard for something before the d-man demanded more money from the Isles, but Potvin was a questionable return. In the late 90s, Roberto Luongo was supposed to be the heir apparent for goaltending duties on Long Island and it would have made more sense to get a forward or defenseman in return for Berard rather than bringing in a veteran netminder.

4.) Traded Bryan McCabe, Todd Bertuzzi, & 3rd Round Selection (Jarko Ruutu) for Trevor Linden – Bryan McCabe, Todd Bertuzzi, and Trevor Linden have all had good careers in the NHL, but the potential that Milbury gave away in this deal make this one of his most awful transactions as the GM of the Islanders.

When the Islanders acquired Trevor Linden, many Canucks fans were upset that their team captain and fan favorite was traded to New York. However, Trevor Linden was a shell of his former self after the 1997-1998 NHL season and the talent that the Islanders gave up in exchange for the center was just lopsided.

Bryan McCabe flourished in Toronto and Bertuzzi wound up having 6 straight seasons (1999-2006) of at least 50 points scored for the Vancouver Canucks. Even though Trevor Linden never really worked out for the Islanders, Bertuzzi and McCabe were not given sufficient time to develop on Long Island. Some have pointed out that Bertuzzi would never have succeeded in Long Island because there was so much pressure on him, but that assumption (thanks to Mad Mike) was never allowed to fully play itself out.


3.) Traded Zdeno Chara, Bill Muckalt, & 1st Round Selection (Jason Spezza) for Alexei Yashin – It is very hard to argue that without Alexei Yashin, Michael Peca, and Chris Osgood, the New York Islanders would have made a return to the Stanley Cup playoffs in 2001-2002. However, the long-term effects of this deal are still felt by the Islanders and their fans.

Alexei Yashin went on to become the captain of the New York Islanders, but was ultimately bought out by the organization. Zdeno Chara went on to win the Norris Trophy and Stanley Cup with the Boston Bruins while Jason Spezza turned into one of the cornerstones of the Ottawa Senators franchise. Mike Milbury simply gave up too much potential for Alexei Yashin as soon as he was afforded some job security under Charles Wang and Sanjay Kumar.

Getting Yashin for the short-term would not have been a bad deal, but having Zdeno Chara and Jason Spezza on the same team speaks for itself.

Alexei Yashin (iMatthew: Wikipedia Commons)

2.) Signed Alexei Yashin to 10 Year, $90M Contract – Alexei Yashin’s 10 year deal was possibly one of the worst contracts in NHL-history, second only to the 15 year deal handed to Rick DiPietro. Milbury believed that Yashin would carry the team for years, but the forward was anything but the safest choice going forward for the Isles.


In 2003-2004, Yashin suffered a laceration to his forearm and was never the same player that he was before the injury. After the 2006-2007 season, the New York Islanders bought out Yashin and will be stuck with paying off the forward until the 2014-2015 season. Acquiring Yashin was one thing, but signing him to a mega contract was simply absurd. Even though Yashin posted 50 or more points in four out of his five seasons in New York, he was not the player that Milbury should’ve spent the bank on.

(Icon SMI)


1.) Traded Olli Jokinen & Roberto Luongo for Mark Parrish and Oleg Kvasha – Trading Roberto Luongo and Olli Jokinen was arguably Milbury’s worst move as the Isles’ GM. Mark Parrish was not the focal point in the Luongo deal as Milbury expected great things from the enigmatic Kvasha.

Olli Jokinen wound up having great stints with the Florida Panthers and Calgary Flames and Roberto Luongo managed to make a Stanley Cup Finals appearance with the Vancouver Canucks. Both players could have developed into powerful players with the Islanders, but Milbury’s dealings on June 24, 2000 will forever haunt Islanders fans.

Mark Parrish wound up being a fan favorite in Long Island and scored some key goals during his stint with the team. On the other hand, Oleg Kvasha wound up being a major bust and was among the many players that Milbury mistakenly put his trust into.

What Could Have Been

It has been constantly mentioned that a team of NHL superstars could have been created from Islander castoffs from the mid 1990s to early 2000s. Players like Bryan Berard, Bryan McCabe, J.P Dumont, Olli Jokinen, Roberto Luongo, and Todd Bertuzzi all had great careers in the NHL, but it is a moot point to think of what could have been. Islanders fans have to take solace in the fact that after so many years, it seems as though the organization’s rebuilding efforts are finally going in the right direction.

Players such as John Tavares, Matt Moulson, P.A Parenteau, Michael Grabner, and many other young players have been assembled by GM Garth Snow as he tries to restore the franchise to glory. It is easy to cry over spilled milk, but for the first time in a long time the Islanders’ fortunes seem to be looking bright. An overnight improvement likely won’t happen, but fans can now be reassured that pieces such as John Tavares, Ryan Strome, and many others won’t be traded based upon the General Manager’s every whim and impulse.

Anatoliy Metter

  • Claven455

    But the Islanders will be leaving in 2015 making the last 20+ years a slow merciless death march into oblivion. You need to merge the Dipietro drfaft pick and the Luongo trade to really show the insanity of that move.

  • Gabor66

    He also traded away Ziggy Palffy, and Darius Kasparaitis!
    Those trades have to make the top ten worst ones….

    • Anatoliy Metter

      I would’ve included the Ziggy Palffy deal, but that was also on the Isles’ management of the time. Milbury was operating under a very tight and frugal budget, so he was essentially forced to deal away Ziggy, much like J.P Dumont. Kasparaitis trade was creeping up on the top 10 though lol.

  • Rizy_y

    lol, great article. –>(The title of the piece is, “Top 10 worst Mike Milbury Trades, Contracts, and Transactions”). exactly what i thought after reading the first three words of the first post

  • nyifancentral

    So how come the good trades and draft picks are not included?

    Milbury robbed Toronto blind twice for the pick that brought Luongo/Brewer and he robbed them of Kenny Jonsson.

    He also traded for Czerkawski, who helped them return to the playoffs, then moved him to Montreal for Asham as the Isles beat out Montreal for the playoffs in 2003, then got Czerkawski back where he had another 25 goals and again the team went to the playoffs in 2004. He also robbed the Kings for Jason Blake and Anaheim for Trent Hunter.  He also moved a top prospect for Aucoin and did a good job with the Peca trade. 

    What could have been? All those players you are writing about have zero Stanley Cups aside from Rupp and Chara and all of them have moved on many times. Chara was part of a Boston team that blew a 3-0 series lead, who Ottawa could not pay as Florida could not pay Luongo who has his meltdowns.

    So if Milbury’s such a bad gm how come he made all those playoffs while Sather’s Rangers missed the playoffs with double the payroll? How come Yashin’s Islanders kept beating out Messier’s Rangers with Kvasha, Bates, Robitaille, Weinhandl as his linemates?

    2001-02 the Islanders had the fourth biggest season turnaround in league history. A lot of teams did not go to three playoffs in three year during that era.

    Florida has not gone to a single playoff, with a lot of franchises making one playoff at best.

    • Anatoliy Metter

      The title of the piece is, “Top 10 worst Mike Milbury Trades, Contracts, and Transactions”, but thanks for reading NYIFC.

    • Cmillen77

      nyifancentral is a moron! unless you are milbury. How can you defend that loser!! He screwed the islanders for over a decade!! The article speaks for itself. I believe the biggest bone head milbury move was drafting Dipietro 1st overall. We had luongo already!! Milbury is a joke. If you can try to google nhl 2000 draft and look at brian burkes reaction when they announce Milburys Luongo trade and the drafting of Dipietro. Burkes reaction is classic. Listen

      • nyifancentral

        Seems like you are not very adult to acknowledge there are two sides.

        No doubt this site will not do an article on Milbury’s best trades to be fair.

        I’m not a fan of Milbury, but he had owners who demanded he make trades to cut payroll, he was told spend one month and cut the budget to nothing the next. He signed Linden and then Nassau made Milstein so angry he tried to break the lease and forced a Palffy holdout and then wanted Milbury to send Palffy to the Rags and leverage the cable contract money.

        Before that he Spano, Pickett and the four clowns.

        What did Luongo do but watch the Isles in the playoffs before he demanded out of Florida? Vancouver would rather Schneider start big games but are stuck with the goalie who lost a playoff series in overtime waving his arm arguing with a ref as the winning goal went past him.

         Burke’s classic reaction was to trade two top picks to a team that won the Stanley Cup for Phil Kessel in a Milbury-like move.

        Overall like it or not after seven years without playoffs Mike Milbury thought about finally saving his job and winning immediately after Wang’s first year. He filled the seats and his team made three straight playoffs because that’s what people wanted.

        What happened the first season Milbury failed to make the playoffs under Wang after 2002? He resigned.

        • Bruce Hollingdrake

          I don’t appreciate you guessing what I would or would not publish. I don’t believe we’ve met, what makes you think you know about my fairness. I would happily publish an article on Milbury’s positive moves – as long as it was well written. Feel free to submit one, my info is under the Join Us link.

          • nyifancentral

            Funny, I don’t recall writing the name Bruce Hollingdrake in my postings.

            However if you are going to inject your sites views on what is fair or not you can find someone to do the best trades made by Mike Milbury or write one yourself without asking me.

            That’s what fairness constitutes, you write one side, then the other so everyone has a balanced view.

            • Justin Johnson

               You’re wrong nyi. I have read the newspapers in Philadelphia for the last 20 years and every paper has a different columnist with a different opinion on a person. This was not an article bashing Mike Milbury personally it was a list of what the author felt about the weaker trades. I thought it was very good. If you’d like I can send you links to articles from major news outlets in the country that do the same thing every day. I completely disagree with you here. The title was not misleading at all. Great read, Anatoliy.

            • nyifancentral

              I did not write anything about the title, I asked how come his best trades or an article about them were not written or the positive results some of those trades brought the club in the short term?

              The article was shabby and ignores all of those future so-called star players won absolutely nothing and were traded many times after leaving New York.

              Olli Jokinen had great stints with Calgary before they dumped him on Cablevision and got him back again. I remember how Calgary humiliated him a few times. Olli’s good at going home in early April without Mike Milbury to blame anymore.

              Alexei Yashin his last season here was on a 90 point pace and made Jason Blake a 40 goal scorer with Chris Simon as his left wing before he hurt his knee and finished with 50 points in 58 games.

              My condolences living in Philadelphia, Ed Snider says jump and Tim Panaccio, Jay Greenberg say how hi in praising the Flyers who dump their front-loaded disasters on other franchises as we head to our next lockout.

              Hopefully Nabokov does not want Bryzgalov’s contract which Snider was willing to give him a few years ago before he bolted for the KHL.

            • Anatoliy Metter

              Thank you for the comment and support Justin. NYI, I really don’t think you understand where I’m coming from at all. This article was a comprehensive breakdown of the man’s WORST transactions, it says it in the title. Why would I include the good trades and transactions in the worst trades and transactions? Some general managers don’t get to make even 3 bad deals before they’re out, but Mad Mike managed to make 10. Go ahead and compare Milbury to another GM who has had bad transactions. The bottom line remains that Milbury had many many bad trades, he had some very good transactions, trades, and even steals, but at the end of the day, the bad outweighed the good, and by a significant margin. There were also many “head-scratcher” deals. Deals where Mike literally gave up nothing for nothing and was seemingly making a trade for the sole purpose of making a trade. If you think that this site puts out slanted work, then it may not be for you. My editor and the various writers on this site do a great job of producing relevant content. If you feel that we don’t, then that’s fine, but please keep your biases to yourself, especially when you ASSUME what this site, it’s authors, and editors are all about.

            • nyifancentral

               Seems you and the editors are extremely sensitive, please don’t tell me what I assume or that I’m bias.

              I simply asked why can’t we get an article to balance it out? Is making such a request an accusation of the site being biased? No.

              I did compare Milbury to another gm in the same market in Sather and wrote about the Islanders beating out a team for the playoffs three years in a row with half the payroll.

              Sather still has his job.

              Some gm’s don’t even get to make three bad trades before they are out? Seems most stick around for years and we have teams in the league that had lost a lot longer than the Isles in the last decade much less a franchise that went to four playoffs in five years before a ton of years in leading the NHL in injuries.

              Milbury’s overall trades took a team that missed the playoffs seven years in a row in 30th place to a 46 point improvement in one year and a point out of first place which was the fourth biggest single season turnaround in NHL history.

              No one is claiming he’s great or even good, but there are two sides to every story.

              The first time under Charles Wang that Mike Milbury’s teams did not make the playoffs he resigned.

            • Meat Mayos

              You seem to have done much research on the beneficial transactions completed by Milbury during his years as the Isles’ GM, so why not submit his top ten best trades and transactions to this site and be done with it?  Then there will be ‘balance’, as you so put it.

            • nyifancentral

              Because the people who write the articles on the worst trades such balance it out on the best trades. That’s what fair is.

        • Bourne_Endeavor

          First and foremost, you are misinformed, a lot of thing, but we shall stick to the Canucks. Luongo did not demand a trade and has openly conceded contract talks had seemingly gone smoothly from his perspective and that he was shocked by the abrupt nature of the trade. Nevertheless, once arriving in Vancouver, he has posted stellar numbers, be nominated thrice for the Vezina, twice for the  Lester B. Pearson and once for the Hart throughout his career. We are content to have him start over Schneider, as despite a slow start, he has again been fantastic this season. 

          Put your bias views aside and look at the caliber of players left by the wayside. Speeza, Luongo, Chara, Heatley/Gaborik (had DP never been drafted), McCabe, Bertuzzi. Teams would kill for that many elite players. Put to perspective…

          Gaborik – Spezza – Bertuzzi
          Blake – Jokinen – Dumont

          Chara – McCabe


          Just throwing together players and look at what you get. That is amazing talent. Milbury may have had bright spots to his GM career however they were overshadowed by how dreadful his bad ones were.

          • nyifancentral

            I don’t know who “we” is with regard to Luongo but it was widely reported he wanted out of Florida and had to be practically given away. The most defining moment of his career is the ot shot that got past his because he was waving his arm arguing with a ref, the people in Vancouver would prefer Schneider if not for Luongo’s massive front-loaded contract he would be starting.

            As for New York all of your so-called elite players never won anything here or where they were traded and outside of Spezza all of them have been traded many times and Spezza was getting the Yashin treatment from the fans in Ottawa. Chara won a cup on the same team he blew a 3-0 series lead with to a team with no goaltending.

            All of these players were moved over money or declining ability.

            It’s over a decade later, the verdict is in, those players brought the teams they were traded to virtually the same that Mike Milbury’s trades produced, a few playoff and no Stanley cups.

            • Anatoliy Metter

              Except those players got to experience a playoff round victory at one point or another and contributed to the success of their respective teams. All that wheeling and dealing by Milbury and the Isles were still unable to win a playoff round or claim that they did anything but make the playoffs. Mortgaging the future for 4 first-round playoff appearances? Sounds like a fair deal to me.

            • nyifancentral

              So if the Isles won game seven in 2002 after Peca and Jonsson were ambushed earlier in the series it all would have been worth it? Forgive me but I saw the Isles win 19 playoff series in a row. Guess I missed all the playoffs Luongo and Jokinen made in Florida or all the cups none of those players in these trades never won besides Mike Rupp before they were traded by the teams the Isles moved them to.