General Managers, it's in the name, must manage a lot of general functions and operations for the franchise they are working for. So, in order to be a good, if not great, general manager you should probably be patient, understanding, and have forethought.
Mike Milbury’s GM career shows very few signs of such things. Milbury’s tenure on Long Island was a decade of troublesome decisions, followed by irrational short term thinking, which in turn led Milbury to become one of the worst ever general managers in NHL history.
His moves were made with passion and fire, just like Milbury spent his entire playing career, whether it be on the ice or even up in the stands fighting visiting fans on the odd occasion. Despite Milbury’s passion being clear during his tenure in Long Island, his success rate in terms of his managerial decision making was very, very low.
When first brought in by the Islanders, the hope was that his leadership qualities and passion would be the driving force behind an Islander re-birth in the mid to late 90s. However, Milbury’s choices soon became the butt end of a bad joke and Islander fans quickly came to find that things were going to get much worse before they were ever going to get any better.
15 Traded Brad Lukowich For 3rd Round Pick
One of Milbury’s earliest moves is definitely one to look back on and scratch your head. Going into the 1996 season, Milbury sent young defensive stalwart Brad Lukowich to the Dallas Stars and, in return, he got almost nothing. A third round draft choice in the 1997 entry draft would mean little to nothing for New York once Dallas rose to the top of the Western Conference in the mid-90s. So, in return for a young, improving and solid defenceman, which the Islanders could have most definitely used in their lineup, got a useless draft pick that turned into Robert Schnabel (22 career NHL games). Meanwhile Lukowich went onto win a Stanley Cup with Dallas.
Just for the sake of it, let's compare both players stats with their respective new teams. Brad Lukowich would play 224 games with the Stars before moving to Tampa Bay, only scoring 29 points, but playing great in his own end, ending with a rating of +14. On the other hand, Robert Schnabel never played a game in the NHL, while getting into 22 games with the Predators, scoring a grand total three points.
14 Traded Janne Niinimaa For John Erskine and a Pick
After arriving a few years prior in a stinker of a trade from Mike Milbury which we discuss later on in this list, Janne Niinimaa quickly found himself out of town in another one of Milbury’s finer failures. While trying to move the defenceman and his contract, the only suitor he could find was the Dallas Stars. In order to make the deal, Milbury swapped a fifth round pick for a second, a very, very slight win for Mike, but gave Niinimaa away for nothing more than a goon. Erskine never did anything more than fight throughout his entire NHL career and even a salary dump move such as this could have been executed better. On top of that, to sadly make matters worse, he would fight for other teams, as Erskine only played 34 games with the team, finishing with a single goal and a rating of -12. He'd late go to the Washington Capitals, where he'd a respectable tenure for eight years.
From the Stars perspective, Janne Niinimaa didn't offer them very much on the ice, but they did use him to acquire Mike Ribeiro, who was a capable scorer for them over six years, scoring 407 points in 461 games.
13 Traded Tommy Salo for Mats Lindgren
In the midst of the Milbury madness, one former Islander goaltender caught quite a bit of flack from the former GM, even more than the other four or five goalies who didn’t last too long during Milbury’s time in New York. Tommy Salo was a solid young Swedish netminder, who was showing some signs of promise in his first few years on the Island. However, Milbury felt compelled to rid himself of a goaltender whom he didn’t have the greatest relationship with publicly. In doing so, he sent Salo to Edmonton during the 1999 trade deadline for a sparsely used forward in Mats Lindgren and an eighth round selection in that year's draft. The most positive piece of the trade for New York was that used that draft pick to get Radek Martinek in the draft, as he had a few solid seasons on Long Island but Tommy Salo got the last laugh against Milbury by reaching the post-season in three consecutive years with Edmonton.
The only other positive to take from this trade is that Tommy Salo wasn't a member of the New York Islanders when he let in the worst goal in Olympic hockey history against Belarus in 2002.
12 Traded Brad Isbister and Raffi Torres for D Janne Niinimaa and Picks
Remember that terrible Janne Niinimaa trade we discussed earlier? Well, this is the other terrible trade that brought the Finnish defenseman to Long Island in yet another masterclass from Mike Milbury.
During the deadline of the 2002/03 season, the Islanders Mike Milbury was looking to give his team a shake up. Milbury had been wheeling and dealing at the deadline already (see the next entry) and continued the shake-up by dealing a hard working pair of forwards in return for a solid puck moving defenceman. Isbister was not much of a threat offensively anymore and therefore the trade was really the young Raffi Torres, drafted 5th overall in 2000, for Janne Niinimaa and a few future draft picks. Torres had a lot of potential and had yet to show it, while Niinimaa had proven himself as a solid two way defenceman. However, Milbury made a move for a veteran who was on the decline and gave up a youngster with a lot of potential and promise. The move came back to bite him within a year or so, as Torres had become a regular in the Oilers lineup and Niinimaa was a forgotten piece on the island.
11 Traded Chris Osgood and a 3rd Round Pick for Justin Papineau and a 2nd Round Pick
Before you mock Chris Osgood for his strange mask and the fact that he achieved most of his success behind a terrific Detroit team, it's unfair to take away his accomplishments for these reasons, as Osgood was good enough to receive votes for the Vezina trophy in four different seasons.
Chris Osgood was in the middle of only his second season on Long Island after having arrived from Detroit prior to the 2001/2002 season. After dragging the Islanders on his back to the playoffs in 2001/2002 on the strength of his fifth 30+ win season at the time, Osgood and the Isles were bumped by Toronto from the first round in seven. The next year, Osgood was traded at the deadline to St. Louis after struggling somewhat during the season or at least in the eyes of the impatient Mike Milbury. In return for a playoff capable goalie, the Isles received a grinding winger and a second round selection that turned into pretty much nothing. Papineau would only last 69 games with the Islanders, while Osgood, on the other hand, went to the playoffs that year with St. Louis, and then went onto with another Stanley Cup in Detroit a few years later.
10 Traded A 4th Round Pick For Alexander Karpovtsev
At the time, Alexander Karpovtsev was a veteran defenceman in his early thirties that played solid third pairing minutes in Chicago for a mediocre Blackhawks club. For no real reason whatsoever that can be drawn up from Karpovtsev's past history or statistics, Milbury felt the need to add the veteran defenceman to his squad late on in the year. Karpovtsev only played three games with the Islanders and, in return, they gave up a draft pick that turned into future cup winner Niklas Hjalmarsson. Hjalmarsson has been an important part of the Chicago top four defensive pairings over his nine seasons with the Blackhawks. This is a tough one to entirely blame on Milbury as it's hard to predict that a fourth round pick will become a top defenceman, but it doesn't change the fact that this was a bad trade.
If we take a quick look at Hjalmarsson's stat-line with the Blackhawks, Islanders fans will likely cringe, but we'll do it anyway. Since breaking into the team in 2007/08, he's played 550 NHL games, scoring 125 points and maintaining a terrific rating of +97. And it's not as if Chicago is hiding him away on the third pairing, as he's averaged over 20 minutes per game since he entered the league.
9 Drafted Rick DiPietro First Overall
Going into the 2000 NHL Entry Draft, many expected the Islanders to add depth to their scoring. Also, there really was no reason for the Islanders to add anything but young offensive talent considering they had a young and upcoming Roberto Luongo in their system with just a year under his belt of NHL action. If you haven't heard of Roberto Luongo, which we highly doubt if you're reading this article, here's a little sampling of his accomplishments: He's won 502 games. He's won the Jennings Trophy. He's a multiple time All Star. He's been nominated for the Vezina trophy on three different occassions. He's a two-time Olympic gold medal winner.
So, what did the Islanders do? They turned heads around the NHL with their first overall pick coming in the form of a goaltender. While DiPietro had great upside and showed signs of promise in the early 2000s, he still was a massive bust. Marian Gaborik and Dany Heatley went with the next two picks. That hurts.
This terrible draft pick led to another terrible trade which we'll discuss a little bit later as well, but you've likely already guessed that it includes a certain All Star goalie that we just heaped plenty of praise on.
8 Traded Darius Kasparaitis and Andreas Johansson for Bryan Smolinski
This was a pretty awful trade for Milbury to start his time in New York. Bryan Smolinski came over from Pittsburgh and while he was able to give the Islanders a little bit of scoring depth, he never scored more than 56 points for them. The idea at the time was to put someone in the middle for Zigmund Palffy. Smolinski lack of touch didn’t quite cut it as a feeder for Palffy, as he only managed 139 points in 227 games for the Islanders, while bringing very little in his own zone with a poor rating of -14. His paltry point totals for a first line center were not worth Kasparaitis’ defensive abilities and brute force.
While Kasparaitis didn't finish his NHL career with many fans due to his dirty play, there's no denying that he was great in his own zone and could offer a lot to any team they would put up with his antics. Kasparaitis went on to have a +24 rating in Pittsburgh in 1996/97 and play another decade in the NHL as a strong defensive-minded defenceman. While he never won a Stanley Cup, he went on several long runs with the Penguins and later with the Colorado Avalanche.
7 Traded Zigmund Palffy, Bryan Smolinski, Marc Cousineau and 4th round pick for Olli Jokinen, Mathieu Biron, Josh Green and 1st Round Pick
Zigmund Palffy broke through in his third season as a frontline goal scorer in New York, scoring 43 goals for a team that desperately lacked offensive flair. A few short seasons later, and two more 40+ goal seasons later, the Islanders were in the midst of a contract dispute with another one of their star players. Palffy felt undervalued by ownership and Milbury, so they moved Palffy during in June of 1999. Palffy took his 40+ goal scoring to Hollywood alongside depth centerman Bryan Smolinski. In return, the only value that the Islanders received came in the form of a first round draft pick and a young Olli Jokinen due to the NHL not allowing the trade to go through without the Kings making their young Finnish prospect a part of the deal. You know it's a bad trade when the NHL vetoes your move because of just how unfair the deal really is. The only other time we remember that happening was when the NBA vetoed the Chris Paul trader.
Now, you might be thinking that the trade couldn't have been that bad if they acquired Olli Jokinen, a star player for the Florida Panthers, but another move on this list will demonstrate why that truly isn't the case.
6 Traded J.P. Dumont for Dmitri Nabokov
J.P. Dumont was a terrific skilled winger in the Islanders organization who had yet to break into the NHL while playing his junior hockey in the QMJHL. His contract disputes prior to getting onto the ice with the team made Milbury uncomfortable and clearly didn’t help Dumont’s chances of winning over the general manager. So prior to the Draft in 1998, Milbury sent the young winger to Chicago for young, unknown center Dmitri Nabokov. Nabokov played 30 games with the Islanders and left for Russia never to return. In those 30 games, he managed an incredible four goals and 13 points. Can you sense our sarcasm there?
What ended up happening with the young winger from Montreal? Well, Dumont would go on to become a solid scoring winger, eclipsing the 20 goal mark on six different occasions. He'd never be able to crack 30 goals in a year, but he did get close in 2007/08 when he managed to put 29 pucks by opposing goalies. He was also known as a gentlemanly player, as he received votes for the Lady Byng trophy.
5 Traded Bryan Berard for Felix Potvin
The Calder Trophy winning Bryan Berard was a speedy, puck rushing defenceman blessed with great hands, who was once the first overall pick of the Ottawa Senators. He was a sure fire All Star who could have been so much more, if it wasn't for the terrible eye injury he endured while a member of the Toronto Maple Leafs.
Now, in terms of the trade, it's hard to see how it made any sense. Before Milbury had arrived, they had traded Wade Redden to get him, while also receiving Martin Straka, which isn't a terrible move. Berard was coming off a Rookie of the Year campaign in Ew York that was followed by an equally good sophomore season. During his third season, Milbury decided to ship Berard off to the Leafs in return for veteran goalie Felix Potvin. Potvin would last all of 33 games in New York, winning just seven of them while maintaining a terrible GAA of 3.35 and an equally terrible save percentage of .893.
With Potvin’s career on the decline and Berard’s really just beginning, this was easily a horrific move on the part of the general manager.
4 Signed Alexei Yashin to a 10 Year, $87.5M Contract
A 10 year, $87.5 million contract was signed by Alexei Yashin as he arrived in Long Island. Before having even played a game with the team, Milbury signed him to an outrageously long and overpriced contract. Later on in his tenure, he was handed the captaincy. After great captains like Clark Gillies and Denis Potvin, Islanders fans got this enigmatic star.
Yashin only lasted five years with the team, scoring 290 points in 346 games and leading them to four first round playoff exits. He was also abysmal in his own zone, finishing his time with a rating of -24. In those playoff series, Yashin essentially vanished, scoring 12 points in 22 games, with a -5 rating that didn't really help anything. In his final season, he only played 11:45 per game in the playoffs, as the powers that be gave up on him.
They decided to buyout his contract in 2007.
3 Traded Roberto Luongo and Olli Jokinen for Oleg Kvasha and Mark Parrish
This trade will always hurt most because of Bobby Lou, who we already discussed at length earlier in the article. However, it's easy to forget Olli Jokinen was also an 80+ point player with Florida twice in his career and had four seasons with 30+ goals. Jokinen’s scoring would have really helped the Islanders and Luongo’s great goaltending career would have too. Jokinen would become a true star with the Florida Panthers, hitting 89 and 91 points in consecutive seasons will playing in the Sunshine State. He bounced around the league after leaving Florida, but he was always a solid forward that teams loved having on their teams. Both had just one season under their belt with the Islanders when this deal was made in return for two forwards who never topped 60 points.
Parrish was the better of the two, but was never elite and could never match the careers of both Luongo and Jokinen. He scored 30 goals on one occasion and finished his Islanders career with 118 goals in 345 games.
Menawhile, Oleg Kvasha was never an effective scoring forward.
2 Traded Bryan McCabe, Todd Bertuzzi and a 3rd Round Pick for Trevor Linden
Trevor Linden was coming off of an injury in 1997/98 and was never was able to regain quite the same scoring touch. He managed only 64 points in 107 games and the usually steady center wasn't great in his own end, finishing with a poor rating of -15.
In return for his year and a half on Long Island, Milbury gave up Bryan McCabe’s quality defensive and offensive skills, as well as leadership, losing a possible future captain. McCabe would go on to have an extremely solid career, scoring 145 goals in 1,135 career games while being a steady and physical presence in his own end.
He also gave up Todd Bertuzzi, who'd turn into an elite power forward in the NHL. Before his ugliness with Steve Moore, many would've considered Todd Bertuzzi the top power forward in the entire NHL, as he had 46 goals in 2002-03 and even received votes for the Hart Trophy.
A pair of bright futures were lost for a burnt out bulb in this very lopsided deal.
1 Traded Zdeno Chara and the 2nd Overall Rick (Jason Spezza) for Alexei Yashin
This is possibly the worst trade in team history and Milbury’s crown jewel. On top of team history, this probably one of the worst trades in NHL history and definitely ranks in the top 5 on that list. Alexei Yashin was a player few teams felt comfortable bringing into their lineup, especially with his personal lack of playoff success and attitude/work ethic issues. Still, Milbury gave the Senators a top young defenceman with lots of upside, a guy named Zdeno Chara. Zdeno Chara would turn into one of the best defenseman in the NHL and one that many consider to be a sure-fire Hall of Famer. Chara has won a Norris Trophy, has been nominated for many more, and won a Stanley Cup with the Boston Bruins as their leader. In 1,274 NHL games, Chara is a staggering +200.
Along with that blue chip prospect, he served up the second overall pick in that year’s draft, which turned out to be Jason Spezza. Spezza has gone on to become one of the NHL's most under-appreciated forwards. In 13 years, he has 812 points in 843 games, as he's scored at nearly a point-per-game rate.
Milbury sure knew how to ruin a franchise’s future in just one deal.