It seems like a simple enough question, doesn't it?
Twins Daniel and Henrik Sedin, from Örnsköldsvik, Sweden, had played hockey together since they were little kids. Daniel, the scoring winger, and Henrik, the playmaking centre, began playing for their hometown MoDo hockey club in 1994. In their first season playing for the MoDo under-16 junior club they finished second in the U16 championship to Djurgårdens, and finished first the next year. In 1996 as 16-year-olds they began playing for MoDo's under-20 junior club and led the team to a second-place finish. By the time they turned 17 they began playing at the top level, Elitserien.
In the 1998-99 season, as 18-year-olds, they jointly won the Guldpucken—the "Golden Puck"—the award for best player in the Elite League. MoDo finished atop the standings but lost the Le Mat Trophy to Brynas, with Daniel leading the team in scoring in the regular season and playoffs and Henrik third in the regular season and second in the playoffs.
The hype surrounding the brothers was enormous going into the 1999 NHL Entry Draft. They were the best young prospects from Europe by far, the best in a long time. There was, however, a catch: if they were going to come over to North America they wanted to play together. Any NHL team that wanted to draft one was expected to draft the other, otherwise neither would come over. At least that was the rumour spread by their agent, Mike Barnett.
The other consensus top-three prospect was Patrik Stefan, a Czech centreman who left the Czech Republic as a 17-year-old to play in North America. Rather than go through the Canadian Major Junior system or the NCAA he signed a 25-game try-out with the Long Beach Ice Dogs of the IHL. His try-out was a little rough but he acclimated to the North American game very well by the '98-'99 season. In 33 games playing full-time with the Ice Dogs he scored 35 points. Not bad for a kid playing with men.
Despite the glowing reviews of his performance on the ice the fact that he was limited to only 33 games in the '98-'99 season drew a lot of negative attention. He had suffered more than one concussion that year.
After the expansion draft on June 25, 1999, Canucks GM Brian Burke was swiftly working out the details of the trades that would get him both Sedin brothers at the entry draft the very next morning. Going into the entry draft the Tampa Bay Lightning, the last-place team, held the first overall pick. The expansion Atlanta Thrashers held the second overall pick, the Canucks had the third pick, and the Blackhawks held the fourth. Patrik Stefan and Daniel Sedin were expected to be the first two picks, so Henrik would almost certainly be available when the Canucks made the third pick. Somehow he needed to wrestle one of the top two picks from either the Lightning or Thrashers, keep his third overall pick, and have assurances that whoever ended up with the first or second pick picked Stefan instead of Daniel Sedin.
The first deal Burke made was with Bob Murray of the Blackhawks. The Canucks would trade defenceman Bryan McCabe and their first-round pick in the 2000 or 2001 Entry Draft to the Blackhawks for fourth overall in '99. The deal was agreed upon on the evening of the 25th and filed later so as to keep Don Waddell of the Thrashers and Rick Dudley of the Lightning in the dark on Burke's machinations.
In the wee hours of the morning Burke was in discussions with the Thrashers about the second overall pick. Waddell was willing to pick one of Daniel Sedin or Stefan, but Rick Dudley wasn't going to take Stefan. Burke needed to get the first overall pick from the Lightning, and even if he did there was still a chance that the Thrashers would take one of the Sedin twins with the second. He needed assurances from Waddell that he would take Stefan instead. Burke needed to make it worth Waddell's while, so Burke made him an offer: he'd give Waddell first overall, on the condition that Waddell used it on Stefan. Waddell agreed, but it was all contingent on the Canucks acquiring the first overall pick from the Lightning.
The Lightning for their part had picked first overall in 1998 and chose Vincent Lecavalier after engineering a trade for the pick with the San Jose Sharks. Another first overall pick wouldn't have hurt but they were amenable to trading the '99 first overall pick for other assets. Rich Winter—Patrik Stefan's agent—wouldn't release Stefan's medical records to any of the top teams, which scared off Rick Dudley. If he kept first overall he was going to pick Daniel Sedin.
When Burke showed up at the FleetCenter on the morning of the 26th he laid it all out to Dudley and Lightning Assistant GM Jay Feaster on the draft floor: he had the third pick, he acquired the fourth pick from the Blackhawks, he had an agreement with Don Waddell that Waddell would take Stefan, and Burke emphasized that he was not leaving the draft without both Sedin twins.
Dudley was also in discussions with the Rangers. The Rangers wanted to take Calgary Hitmen forward Pavel Brendl, who probably would have been available at the fourth overall pick, but the Canucks had acquired fourth from the Blackhawks. If the Lightning could get the Rangers the fourth overall pick they would trade Niklas Sundstrom, Dan Cloutier and their first and third round picks in 2000 for it.
The plan was set into motion: Burke acquired the first overall pick from the Lightning for the Blackhawks' fourth overall pick and two third round picks—the compensatory pick for the signing of Jyrki Lumme and the Sabres' pick, which they had acquired earlier for Geoff Sanderson. Then he traded the first pick to the Thrashers for the second overall pick and a conditional third round pick in 2000. The Lightning traded the fourth overall pick to the Rangers for Sundstrom, Cloutier and their first and third round picks the next year.
Going into draft day the Lightning held the first pick, the Thrashers had second, the Canucks third, the Blackhawks fourth. At the end of the day the order went Thrashers, Canucks, Canucks, Rangers. The Thrashers took Stefan first, the Canucks took both Sedin twins with second and third picks (Daniel officially went first) and the Rangers took Brendl.
Brian Burke's manoeuvring at the '99 draft is still considered some of the most shrewd asset management in NHL history. 15 years later the Sedin brothers still play for the Canucks, and are the club's all-time leading scorers (Henrik, despite being chosen after his brother, has more points than Daniel).