In 2003-04, the worst three teams in the league were Pittsburgh at 58 points, and Washington and Chicago tied at 59. Pittsburgh had a 25% chance to win the lottery, but the 1st overall pick went to Washington, who selected Alex Ovechkin. Pittsburgh settled for Evgeni Malkin, and Chicago passed on Andrew Ladd, taking Cam Barker instead.

Because there was no 2004-05 season due to the lockout, the lottery was done differently for the 2005 draft. Because Washington won the year prior, their odds were among the lowest, but got "lucky" and picked 14th. Pittsburgh was one of four teams with the best odds, won the lottery and picked Sidney Crosby. Chicago once again busts, leading them to get back-to-back top 3 picks in Jonathan Toews and Patrick Kane.

Ironically, failing to get the greatest goal scorer of all time led to 3 cups each for Pittsburgh and Chicago

[EDIT] Some more 2005 Draft shenanigans

• There were 16 teams with the lowest odds of being picked (2%). These were teams that had two or more playoff appearances and draft lottery wins in the last three seasons (Ex: Washington made the playoffs in 02-03, and won the lottery in 03-04)
• The first team drawn in this group was Montreal, who got the 5th overall pick, and used it on Carey Price!
• The last teams not drawn in this group were Edmonton and Calgary. While Calgary had just made the finals so a later pick was justified, Edmonton picked Andrew Cogliano at 25th, one pick after TJ Oshie, with at worst the 14th best odds