In looking at the past and present managerial personalities for the Pittsburgh Penguins, you could see several options where you could have a night on the town, a classy night in, and maybe even get in a little too much trouble. So, I guess it would depend on what type of night you wanted to have.
Some key names jump off the map when thinking about who you would want to spend the evening with such as, the current Pens manager Mike Sullivan, the man with 9 rings, Scotty Bowman, or the legendary Badger Bob Johnson.