The New York Rangers originally picked forward Pavel Brendl fourth overall in the first round of the 1999 draft lottery. Considering how weak this draft was, Brendl was the only forward selected in the top 10 of the 1999 draft lottery in the first round who played fewer than 100 career regular season games.
Instead of being drafted in the fifth round by the Buffalo Sabres in the 1999 draft, goalie Ryan Miller slides up into the first round to play for the in-state rival Rangers at MSG.
Miller is the only goalie from the draft class in 1999 who started over 600 career regular season games and 50 career postseason games in the playoffs. He was a really good starting goalie consistently in the NHL for well over a decade. Miller won a Vezina Trophy for Buffalo in the 2010 season and helped lead the Sabres to the Eastern Conference Finals in the 2006 postseason.
Back-to-back goalie picks round out the top five in this hypothetical reimagining of the 1999 draft lottery, with Craig Anderson going to the New York Islanders at the No. 5 spot. Anderson had a very long and inspiring career in the NHL over multiple decades in the league with the Ottawa Senators and Florida Panthers, among other teams in the league.
The Isles originally picked center Tim Connolly fifth overall in the first round of the 1999 draft lottery. Connolly, unfortunately, was limited in his career in the NHL due to injury issues. Had it not been for nagging injuries throughout his career, Connolly could've been one of the better centers from this draft class from 1999 for the Isles and Buffalo in the 2000s and 2010s.
Forward Radim Vrbata ended up being a steal for the Colorado Avalanche in a pretty shallow draft class in the seventh round (212th overall) in the 1999 draft. Vrbata was a good forward and a quality scorer for a long time in the NHL, playing over 1,000 career games in the regular season over the span of more than a decade in the league.
The Nashville Predators ended up picking goaltender Brian Finley with the sixth overall pick in the first round of the 1999 draft lottery. Finley was the first goaltender selected in the 1999 draft in the first round to the Preds. He only made a handful of starts and played four regular season games in the NHL in his career.
Vrbata slides up into the first round to fall into the top six for Nashville.
Having Vrbata drafted in the top six halfway through the 1999 draft lottery in this first round shows how limited the star talent and depth at the top of the board in this draft class was.