Gord Dineen was somewhere in between.
Gord was the 42nd overall player drafted in the 1981 Entry Draft. The New York Islanders were in the midst of their great Stanley Cup dynasty years, and were looking to reload with young players like Dineen. Unfortunately for Gord, he cracked the team in the 1983-84 season - one season after the Islanders last Stanley Cup.
Gord made favorable impressions that first year, often playing alongside the great Denis Potvin. He struggled to stay in the line up as a top four defenseman for the next couple of years, but finally found his niche by about 1986.
Gord had to work real hard to improve his skating - both forward and backward - to stick in the NHL. He always lacked acceleration, but improved his turns so that was not a liability. As he gained experience and confidence, he became a serviceable depth defenseman though he was never noted for any one strength in particular. He held his own defensively, but lacked consistency in the physical game. Offensively he was a solid first pass blue liner who even made smart pinches when playing well. He seemed to see the ice well, but never put up significant numbers in his NHL career. In fact, in 528 NHL career games he had just 16 goals and 106 points.
Dineen's claim to fame in New York? He assisted on Pat LaFontaine's famous goal at 8:47 of the fourth overtime as N.Y. Islanders beat Washington 3-2 in Game 7 of Patrick Division semifinals on April 18, 1987. Dineen's shot was deflected by Kevin Hatcher out to LaFontaine, who beat Bob Mason from inside the right point. The Islanders traded Dineen to Minnesota in March, 1988, but his stay with the North Stars was short. By December he was traded to Pittsburgh by Minnesota with Scott Bjugstad for Ville Siren and Steve Gotaas.
Dineen may have been really happy to join the Penguins. After all, Mario Lemieux was emerging as the game's best player and was about to lead them to back to back Stanley Cups. But Dineen would not be a part of either championship. After the 1989-90 season he was demoted to the minor leagues for all but a handful of games. Just as in New York, Gord Dineen just missed out on getting his name on the Stanley Cup, just like his dad did 40 years earlier.
Dineen played through these tough times with admiration. He would be rewarded in 1992 when he signed with the expansion Ottawa Senators. Now those Sens teams were amongst the worst of all time, but Gord treasured his return to the NHL nonetheless. He even served as team captain for a while.
Without a contract in the summer of 1994, Dineen re-signed with the organization where it all started - the New York Islanders. The idea was he would be a veteran presence with their farm team in Denver (soon to move to Utah) and eventually lead to coaching possibilities. Dineen jumped at the security, though he kept playing until 2000. He even got into 9 more games with the Islanders in 1994-95, ending his NHL career with the same team as he started it with.
Gord Dineen continued to coach at various levels after hanging up the blades.