101+
I started playing in 1990, when I was in the Navy. In the Navy alone in different duty stations I played with about 30 different people.
Once you add in the various groups I've played in since 1995 when I got out of the Navy (Upstate New York - 2 groups, Austin Texas - 3 groups, Omaha Nebraska - 2 groups) that brings me up to around 100 there with just steady games.
However...
Now you have to add in DragonCon (twice), GenCon (four times), Origins (four times), Arisa (once) and some smaller, local cons...with multiple games at each con.
I'd easily commit to 200 people+ in total.