Imagine if the Sens end up with 2 top 5 picks.
Was trying to think of other 'recent' instances of teams having two picks in the top 10:
1994: Edmonton has picks #4 and #6, take Jason Bonsignore and Ryan Smyth. Along with Alex Daigle, Bonsignore has become synonymous with teams needing to make sure that the prospect actually likes playing hockey.
1997: Boston took Joe Thornton at #1 and then were shocked when Sergei Samsonov was still there at #8. Funny things lost to history is that Samsonov was initially much more effective than Thornton and ended up winning the Calder. Also random trivia, the Bruins had retired every single digit (at the time they figured Cam Neely's #8 would go up eventually) except for #1 and #6. They made Thornton wear #6 at first, with the implication being that they would retire it one day.
1997: To the shock of many, the Islanders take Roberto Luongo and Eric Brewer #4 and #5. At the time the Islanders were well-stocked on D and goalies, so most expected them to take Daniel Tkaczuk and Sergei Samsonov. Islanders arguably made the right picks, but Mike Milbury didn't have the patience to wait it out.
1999: Vancouver gets the Sedins at #2 and #3. Brian Burke would admit years later that he tried to get #1 too and he would have selected Patrik Stefan.
1999: Islanders take Tim Connolly #5, Taylor Pyatt #8, and Branislav Mezei #10. Wrong year to have three picks in the top 10.
2000: NY Islanders get Rick DiPietro #1 and trade back up to get Raffi Torres at #5. Perhaps a time that a team was unfortunate that it won the lottery.
2002: Florida makes an overly complicated trade down but still gets Jay Bouwmeester at #3, then take Petr Taticek at #9.