As a player, Rick Tocchet is most closely associated with the other Pennsylvania hockey team, the Philadelphia Flyers, and he should consider that he spent four times longer there than he did with the Penguins.
John Cullen played college hockey at Boston University. Although he was one of their best players, he went undrafted in the NHL. Cullen left Boson University as the then all-time leading scorer, and he would try out for the Buffalo Sabres, who chose him in a Supplemental Draft. He didn't make the Sabres, so Cullen would instead join Flint of the International Hockey League, wherein the 1987-88 season, he scored 157 Points. As you can imagine, that turned many heads.
A native of Massachusetts, Ryan Whitney, played for Boston University and would be drafted in 2002 by the Penguins 5th Overall in 2002. The Defenseman would turn pro two years later, and after playing in Wilkes-Barre/Scranton (Pittsburgh’s AHL farm team), he debuted in 2005-06.
Dan Quinn was traded from the Calgary Flames for Mike Bullard early in the 1986-87 season, and the Center would go on to have some of his best individual success in pro hockey. He would score 71 of his 80 Points that year as a Penguin, and followed that with a career-best 40 Goal campaign, where he was eighth in the league in Power Play Goals. That was good, but he would top that with a 94 Point year in 1988-89. The Penguins had a lot of scorers by this point, and he was dealt to the Vancouver Canucks halfway through the 1989-90 campaign.