Marcel Dionne did make the 2nd round of the playoff in 1976, 1977 and 1982. However, all of those first round wins were a best-of-5. Here is a shocker, Dionne never won a playoff series that was a best-of-7. Now how's that for a shock? But to be fair I guess he doesn't count here, he did win a playoff series.
Harry Howell is a good choice. If you want to count the WHA he made it past the 1st round in 1975. But the NHL he did not.
Olli Jokinen played in 1231 career games, and then just 6 playoff games, a first round exit. That's it. I would think he has to be the guy here isn't he? I know he probably could have done something to help his teams a bit more, but you have to admit that's pretty hard luck too.
Guy Charron should get a long look here. He never played in a playoff game in his career. 534 points in 734 NHL games. Played on some horrible teams, finished with a plus/minus of -210.
So is there anyone close to Charron, Jokinen or Howell?