Very difficult to say. I voted one more, and I do think the Pens could've came at the bare minimum very close to winning another one between 2010 - 2013. Each team had its own unique strength and weaknesses.
2010 - Deep and talented team, awesome top 9. Bottom D maybe a weakness. MAF absolutely crapped the bed in the 2nd round. Fatigued played a factor, after a Cup win and a SCF appearance the year before.
2011 - Obviously Crosby and Malkin being injured killed this team. Still, I like how they played and with Crosby and Malkin healthy this is probably the 2nd best team in the DB era. This is the only season that I thought DB was good. W/ 87 and 71 this team could have challenged for a Cup. MAF outplayed by 72 year old Dwayne Roloson and team blew a 3-1 lead in the playoffs.
2012 - W/ Sid, the talent was there. This is the year however, where both DB and Shero truly failed. DB sent a message to his team that it was ok to not try defensively. Then the playoff debacle happened. Team also had a weak bottom 6. MAF was playoff MAF. DB should've been fired.
2013 - This team had the offense to win, and a backup goalie (Vokoun) to save the team after MAF pooped the bed. I didn't love the D corps, and I think Shero gave up too much for Douglas Murray. Shero was simply getting random guys, rather than trying to put together a team with a style in mind. Then DB actively tells his team to play physical in the ECF, which took them out of their style, and ultimately lead to their being swept.
2014 - Shero's belief that you could put anyone next to 87 and 71 truly began to show this year. Zero depth.
DB won a Cup with Therrien's team. He did a good job in 2011, but was an otherwise awful coach. He won games because of his roster, not because he was a good coach.
Shero did some outstanding things in Pittsburgh. My main complaint is not firing DB after 2012. No excuses for that. I also think he made some mistakes drafting, and never did a good job building strong forward depth. He was too faithful to old buddies (Adams, Eaton, Scuderi) and I don't think he ever had an idea what kind of team he wanted. Just seemed like he just wanted good players without an actual goal. This is something GMJR has done an excellent job with.