2 Of The Biggest What Ifs For The Philadelphia Flyers Franchise

One such mistake was the team's failure to sign Curtis Joseph, who was a free agent at the time. Instead, they chose John Vanbiesbrouck, who eventually lost his starting position to Brian Boucher and Roman Cechmanek.

Joseph went on to spend four years with the Toronto Maple Leafs, where he achieved impressive stats and provided excellent goaltending during multiple playoff runs.

Another missed opportunity for the Flyers was Raymond Bourque, a Hall of Fame defenseman who spent most of his career with the Boston Bruins. In 1999-2000, Bourque wanted to end his career with a Stanley Cup and expressed interest in joining the Flyers due to his relationship with goalie coach Reggie Lemelin.

However, when the Flyers offered Daymond Langkow and other players in exchange, the Bruins were more interested in Simon Gagne and the deal fell through. Bourque went on to win a Stanley Cup with the Colorado Avalanche in 2001, while the Flyers were unable to advance past the first round in 2000.

Overall, the Flyers made major mistakes by not signing these two talented players.

If they had, they could have had a successful cup run with strong goaltending from Curtis Joseph and excellent play from Ray Bourque. It's another case of "what ifs" in the world of hockey.