On a longer timeline, Glenn has more often been a libertarian type, and his beef with government in the last decade has mostly stemmed from NSA and DHS overreach into the private lives of US citizens, or corrupt schemes to silence political rivals like in Brazil. Greenwald has never really been leftist in the explicit, economical sense, and his left leanings in recent years were borne out of his libertarian free speech absolutist attitudes. That means that as soon as right-wingers like Tucker start crying about being silenced by leftist extremists for "just having views" about trans people or what-have-you, Glenn is very vulnerable to sympathy to those people's "free speech", and he lets that completely override any other moral or ethical considerations.

To him, if a proposed plan of action for the "justice" of a marginalized group may jeopardize their opponents' right to "free speech", including "speech" from the bully pulpit of national media or corporate power that is otherwise morally reprehensible, Glenn's ideology (schniff) demands that he reject that course of action with no further consideration. This, of course, leads him to being a useful idiot stooge for Tucker and Thiel types in our political ecosystem.