1. 08 Wings. this team was an absolute juggernaut with several of the Wings' best players of the 2000s era playing in their prime. I really can't think of a significant weakness they showed. Maybe Osgood was playing over his head a little, but it's not like he had much to cover up for.
2. 16 Pens. I think this roster had a few minor holes compared to the 08 Detroit team - Kunitz/Rust in the top 6 was not ideal, their defense was not quite where it could have been, and Sheary was not up to par as a first line player yet - but their style was so dominant and consistently well-executed that I would easily put them over any of the other teams in question.
3. 09 Pens just the right mix of guys at the right time, despite a bit of a ragtag roster construction. Most notably Malkin's monster 36-point playoff performance (though people seem to forget sid also had 30 points this postseason!) drove their success, but they got big performances in big moments from the supporting cast, especially Gonchar, Talbot, and Guerin.
4. 09 Wings. Essentially the 08 team over again, but they were handicapped considerably by the absence of Datsyuk. Hossa was a good addition but he was kept pretty quiet when it counted.
5. 08 Pens Lots of skill at forward, but too young and green to really assert themselves on the biggest stage. Fleury's stellar postseason contributed in large part to the team looking as strong as it did through the first three rounds, where they only lost 2 games. Malkin also played the entire finals hurt, which was significant problem because he looked terrible.
6. 17 Pens Objectively, I think this is the worst team to appear in the finals out of all of the ones aforementioned. They are winning through sheer force of will, through a constant sequence of injuries to key players and without anything remotely resembling a #1 defenseman who is capable of driving the transition game.