The 1997 Draft
The final season in Hartford ended with the Whalers missing the playoffs for a 5th straight year. They were just two points behind Montreal for the final spot. Additionally, the Boston Bruins were awful, finishing with the league's worst record, giving them the 1st and 8th picks in the opening round. With their picks, the Bruins selected Joe Thornton and Sergei Samsonov, respectively.
Under their new Hurricanes nickname, the team was still active in the first round. The Canes owned Detroit's (#22) and Philadelphia's (#23) picks through trades. The Flyers' pick was traded to San Jose to trade back, while the 22nd pick was used to select defenseman Nikos Tselios. This pick amounted to very little, so it was a rough first round in an otherwise stellar draft class.
If the Canes still had their pick, Samsonov eventually made his way to Raleigh in the late 2000s, but there's a world where he's a Hurricane much sooner. Four picks later at 12th overall, the Senators selected Marian Hossa. Dan Cleary went a pick after Hossa, and he carved out a solid NHL career for himself, too.