Reggie has a big name for his big playoff games against the Knicks and being the former all time 3 point king. But outside of that he's just a very good player, but not great.
There is a very popular website called Basketball Reference which has historical stats on anything you can think of. They have a HOF probability rating which is their own custom formula based on various stats. A rating of 1.0 means you're a slam dunk HOF'er.
Reggie has a rating of .0553; not even close. Some of the more recent players around him are Alvin Robertson, Lattrel Sprewell, Rip Hamilton, Lamar Odom; all decent players who have made a few all star games but not consiered best of the best class.
Now in comparison to the C's future 4 HOF'ers
Shaq: 1.0
KG: 0.9987
Pierce: 0.9768
Ray: 0.9501
Most, if not all, eligible players above 0.75 are in the HOF. So according to that site which uses statistics, not opinions, Reggie is not even close to being HOF worthy. I think many of us who grew up wathcing him thought he had a great chance because for a stretch he was one of the bigger names in the game. But then if you think of his peers during his generation, he does not stack up (MJ, Stock, Malone, Dream, Barkley, Admiral, Ewing, Pip, Shaq).