Florida, on the other hand, has been on the outside looking in for countless years.
But this tie might not be the David vs Goliath matchup the history books initially suggest.
While Pittsburgh is certainly a part of WCHL playoff furniture, they've lifted the WCHL Cup only once, and they've actually succumbed to recurring postseason disappointments in recent years.
Eastern Pennsylvania commentators have long mused that this is due to GM Matthews' insistence on a young pro core. Inexperience and naivety are accusations levelled at this organisation often, at least in contrast to other perennial contenders such as New York .
Inexperience didn't cost Pittsburgh a single step in the regular season - the Pens won the Metropolitan division at a canter, leaving New York firmly in the rear view mirror.
Pittsburgh scored 3.41 goals per game (3rd), conceded only 2.62 goals per game (8th), and ranked 3rd in special team effectiveness.
Led by Sidney Crosby, the Pens take 26.49 shots per game (3rd), and allow only 21.01 shots against per game (2nd). They're also the most disciplined team in the league (12.66 PIM/game).
Florida wasn't as good as Pittsburgh in the regular season. That is an undoubted fact.
It actually took a late resurgence, following the trade for Czech forward Tomas Fleischmann, for Florida to finally surpass Boston in the standings and secure a wildcard berth.
But Florida will not be an easy opponent for Pittsburgh to deal with in the first round.
They scored 3.15 goals per game (10th), and allowed only 2.88 goals against (12th). Those numbers are not a million miles away from Pittsburgh.
Babcock's men are also very disciplined, at 13.70 PIM/game (7th).
Florida's potential pitfall will be its under-performing special team units. They ranked 27th in overall special team effectiveness, though their PK unit has been the main issue.
This series will come down to discipline. If Pittsburgh keeps its cool, and continues its disciplined play, then Peter Laviolette will be able to have his revenge on a GM who fired him only two seasons ago.
However, if Pittsburgh's old inexperience problems resurface, and Florida stays out of the penalty box, Florida might just be able to pull off a first round upset.
ODDS (TO QUALIFY)
Pittsburgh 10/13
Florida 2/1
