Fitzgerald was an important member of the 1993 New York Islanders that eliminated the Penguins in the Wales Conference Finals, ending the Penguins' defense of their two straight Stanley Cups in 1991 and 1992.
He was a team leader on the 1996 Florida Panthers that downed the Penguins in the Eastern Conference Finals in 1996. Not only that, Fitzgerald had the series-winning goal in Game 7.
Now, Fitzgerald is in position to help the Penguins strive for another Stanley Cup. He was asked if Pittsburgh fans have forgiven him.
"I don't know if they do," he said with a laugh. "It's kind of ironic, I guess. Those two times were the most success I've ever had in the Stanley Cup Playoffs. Here we are, 13 years later ... and 16 years later!"
"Tom played on an important checking line for us with Claude Loiselle and Brian Mullen," ex-Islanders defenseman Tom Kurvers recalled. "We needed them, energy guys, because we were completely overmatched by their talent. The Penguins had a great regular season and were a very powerful team. Brad Dalgarno hit Mario Lemieux early in the series and hurt him. Mario played through the injury, but it affected his game.
"We had a little success behind us when we got to that second round, but the challenge was so great, we had to play our best. Glen Healy stood on his head in Game 7 to get us the victory."
Fitzgerald had played parts of the three previous seasons with the Islanders, but 1992-93 was his first full NHL season.
"I remember we snuck into the playoffs and went into Washington and beat them," Fitzgerald said. "Then, we had to face the king of the hill, the Penguins, back-to-back Stanley Cup champions. In those days, when you went into Pittsburgh, you were concerned about surviving but we always had the belief, you never know.
"There's no such thing as a perfect team, but we needed a perfect storm, things had to go right for us and they did. We shocked them in the first game in Pittsburgh and the second game was not a game. We lost 3-0. We went back to our building and won when I had the two shorthanded goals on the same penalty."
For Fitzgerald and the Islanders, the two goals on one penalty kill gave them the boost they had to have against the mighty Penguins.
"Any time a team scores from the defense, it creates energy," said Fitzgerald. "Look what we were up against. Their power play had Lemieux, (Jaromir) Jagr, Kevin Stevens, Rick Tocchet, Ron Francis, Larry Murphy and Joe Mullen. They could only put five on the ice at a time. We just hoped we could get shorthanded goals and give the team a lift.
"For me, it was a case of being in the right place at the right time. I high-sticked Mike Ramsey behind the net, but they called the penalty on Claude Loiselle. Then I batted Joe Mullen's pass out of the air and it could have been high-sticking. I knocked it down and took a slap shot past Tom Barrasso."
"The way I remember it, I went in the box for him. The referee got the wrong player," said Loiselle, now the Tampa Bay Lightning's assistant general manager. "He scored two shorthanded goals on the same penalty and turned the game. The best thing for me to do was stay in the penalty box.”
The Islanders won Game 3, but lost the next two games. After winning Game 6 at home, the Islanders needed to win Game 7 at the Igloo.
"We didn't think doomsday because we were the underdog and had nothing to lose," Fitzgerald said. "We won at home and went into Game 7 thinking anything can happen."
One of those things was a scary injury suffered by the Penguins' Kevin Stevens, who fell face-first to the ice after a collision with the Islanders' Rich Pilon.
"You don't want to see anyone lying in a pool of blood and I think their concern the rest of the game was with Kevin," said Fitzgerald. "But we still had a game to play and went into overtime. David Volek didn't play much in that game, but I'll never forget him going down the side and blasting a slap shot past Barrasso.
"I remember we snuck into the playoffs and went into Washington and beat them. Then, we had to face the king of the hill, the Penguins, back-to-back Stanley Cup champions. In those days, when you went into Pittsburgh, you were concerned about surviving but we always had the belief, you never know."
-- Tom Fitzgerald
Two months after the Islanders' victory against Pittsburgh, Fitzgerald was selected by the Florida Panthers in the 1993 NHL Expansion Draft. The Panthers struggled in their first two seasons but improved dramatically and made a surprising run to the 1996 Stanley Cup Final, beating the Penguins in the Eastern Conference Finals along the way.
"We felt we could win as underdogs against Pittsburgh," Fitzgerald said. "We were a very good defensive team but we had no business being there except for great goaltending by John Vanbiesbrouck. We had a great work ethic and played our system to a 'T.' We got timely scoring and a different line played big in each round. Stu Barnes, Ray Sheppard and Dave Lowry were great in the first series against Boston.
"Tommy's role with us in 1996 was no different than the introduction he got a few years earlier from Al Arbour when he broke in," Vanbiesbrouck said. "Arbour told him, 'Hey kid, you're not a scorer, you better learn how to check.' Tommy lived by that rule, that if he chipped in a goal, it was a bonus but his job was to shut down the big guys.
Fitzgerald had two goals in Game 1, a 5-1 Panthers victory and the Penguins came back to win Game 2. Barnes had two goals to lead a 61-shot barrage in Game 3, a 5-2 Florida win. Lemieux shook off the flu to lead Pittsburgh to a Game 4 victory and then the Penguins shut out Florida at home in Game 5.
The Panthers won 4-3 in Game 6 on Rob Niedermayer's late goal to return to Pittsburgh for Game 7. Mike Hough opened the scoring for Florida and Pittsburgh's Petr Nedved answered before Fitzgerald scored on a long, third-period slap shot from the blue line. Vanbiesbrouck made 39 saves in the 3-1 series clincher.
"After winning Game 6 to force Game 7 back in the Igloo, just as we did with the 1993 Islanders, it felt like Groundhog Day," Fitzgerald said. "We felt the longer we could stay in the game, the better for us, the more they would cheat on us and take chances.
"I scored the eventual game winner with more than 10 minutes to go in the game. I was going for a change and threw a slap shot on net. The puck was on end and it knuckleballed on in. The stars were aligned. I didn't take many shots like that.
"We held on. We played well with a lead and got an empty netter to make it 3-1. We were just proud of our accomplishment against Mario and Jagr. We prided ourselves on competing with them, the greatest players in the league. We had to be on our toes because they could embarrass us with their skill level."
Lemieux and Jagr were held without a goal in the last five games.
"Defensively, they are the best team I've ever played against," Lemieux said.