As it got closer to the 1999 draft, there were two teams looking to make a big splash to turn around bad seasons. The Islanders had stockpiled picks via a firesale, and had the 5th, 8th and 10th pick along with the 28th overall pick. These picks were going to be the cornerstone of a new Islanders dynasty.
Meanwhile the Vancouver Canucks had been freed from the reign of horror initiated by Mike Keenan and Mark Messier. Brian Burke had taken over and was looking to make a big splash in his first draft. His target? Daniel Sedin and Henrik Sedin, highly talented twins from Sweden. Unfortunately, they were reportedly unwilling to play apart, with rumors swirling about how they might work the system so they might both become UFAs. Another problem was that while Daniel was ranked among the top thre prospects, Henrik was ranked at the bottom of the top 10.
It was an amazing amount of maneuvers which eventually got Burke the 2nd and 3rd overall picks in order to take the Sedins. A decade later it was easily the best move of a draft which is considered one of the worst in recent history. The Canucks have become one of the elite teams in the league, winning the President's Trophy this year on the back of award-winning seasons by the Sedins. Meanwhile, those four Islander draftees? They became Tim Connolly (163 games played for Isles) Taylor Pyatt (78 games played for Isles) Branislav Mezei (66 games played for Isles) Kristian Kudroc (26 total NHL games).
But looking back at the draft movement, it isn't hard to imagine that the Isles might have found themselves in a position to draft the Sedins...
To begin with, the Canucks lost their last game of the season to the Flames 5-4, while the Islanders routed the Penguins 7-2 to finish their season. This bounced the Islanders up to the 4th overall pick and the Canucks into the 3rd slot. 70 point Chicago (the Isles had 58 points) moved up via the Draft Lottery and bounced the Islanders from 4th to 5th. Burke then traded Bryan McCabe and the Canucks 1st round pick in 2000 for the 4th overall pick from Chicago. Burke then flipped the 4th overall pick (and some later picks) to Tampa Bay for the first overall pick. Finally he flipped the first overall pick (and some later picks) to Atlanta for the second overall pick and an agreement the Thrashers wouldn't take a Sedin. The rest is history.
The top 4 picks in the 1999 draft were traded 10 times between 4 teams, the first overall pick traded 3 times. At the time some argued this was one of the deeper drafts in recent history. But it isn't hard to imagine that with 3 picks in the top 10, another first rounder and another 10 picks outside the first round, that with a little more luck and smart moves the Islanders could have drafted the Sedins instead.
The Islanders had two 3rd rounders, two 4th rounders and two 5th Rounders. A loss on the final day of the season, and not being completely screwed by the draft lottery, would have left the Islanders with the 3rd overall pick. Then it would have been a matter of getting the 1st overall from Tampa, who seemingly knew something was wrong with that draft as they traded out of the first round altogether.
While it took the Sedins a few years to get going, since the lockout they have each been over 70 points every season. During the same time frame the Islanders have only had 4 players score over 60 points, and no one has gotten 70 points. The only time the Isles had 2 players over 60 points in one season during that time was in 05-06 with Miroslav Satan and Alexei Yashin.
While the Sedins haven't always been the driving force behind the Canucks, in the last decade they have only missed the playoffs twice. It isn't hard to imagine that the addition of the Sedins to the Islanders might have at least made them a much more competitive team in the long run. Tim Conolly managed 70 points in his first two seasons with the Islanders, comparable to the early career of the Sedins.
Of course the one problem with this is that it imagines Mike Milbury having patience and allowing them to develop. That was not a strong suit when it came to Mad Mike, and it's probable that if he had swung the deals to get the twins he would have given up on them, too. Except instead of trading Connolly and Pyatt for Peca, it would have been both Sedins for Peca and change. While Connolly and Pyatt became NHL regulars, their struggles and the Islanders making the playoffs with Peca make up for that trade.
The kicker in all this? The Sedins regular linemate, Alexandre Burrows, was once in the Islanders system. He was at the Islanders training camp in 2002 as a free agent from the QMJHL. He was then sent to Bridgeport and played in a few exhibition games there before the ECHL tryout guys showed up. Steve Stirling liked him and tried to keep him around, but couldn't.