Both were imperfect people in unique situations, but Gladwell's distinction seems to boil down to "Harvard, game theory, & Nobel prize winning PhD advisor" in the case of Ellsberg vs. "community-college dropout" in the case of Snowden, followed by Gladwell falling over himself to redefine "insider" right after spelling it out in detail with the language of class, prestige, and societal privilege.
I don't think Gladwell understands enough about either person - or "leaks" in general - to draw meaningful conclusions.