Longest is a good one.
Close after that would be the Clarence S. Campbell Bowl (presented to the team Captain ..... who is an individual ... a little stretch on the OP).
Outside of all the SC notions though, I'd love to see:
- Nabby win the Brodeur Award,
- Thornton win the Messier Award
- Pavelski win the Selke Trophy
- Marleau win the Rocket Richard Trophy
- Doug Wilson for Lifetime Achievement
- Huskins win the +/- Award
- Nichol win the Masterson trophy
- Heatley win the Art Ross
- Boyle win the Norris
- Murray win the Lady Byng
The chances of these actually happening are iffy to out of the question.