nah, he really doesn’t. if you watch his specials it’s not hard to read between the lines and see which side he leans towards, and if you catch any of his podcast, even clips on twitter or youtube, it’s blatantly obvious where he stands.
again, when the right canceled bud light he kept drinking it so publicly that he became bud light’s spokesperson. when he does his stand up, he doesn’t punch down. if he’s talking about mentally disabled people it’s real-life stories of him volunteering with them, humanizing them to his audience, and basically putting them on a pedestal (and i know you’ve seen the clips of him completely shutting down andrew schultz’s podcast when they made fun of people with downs). when he does make fun of people it’s usually himself, and when it’s not, it’s people like the president, or navy seals. he’s not a guy who punches down to get laughs, which is increasingly rare these days.
then, if you actually do look deeper into his podcast and podcast appearances, that’s when you see him seriously going after right wing figures and right wing ideology. he basically lost his shit over how wildly unprofessional trump’s cabinet was in public at the ufc fight; he recently had a fairly viral clip of him slamming the comedy mothership, where he basically says, “every single set doesn’t have to feature the word retarded, y’all need to dial it back some.”; and while he does make fun of liberals (as he should), i’ve never seen him actually go after liberals or liberal ideology the way he has conservatives and their ideology, ever.
the bottom line, and the tl;dr is that shane gillis’s entire personality and shtick would have been considered right down the middle in the 90’s or even 2000’s, but is often considered “offensive” in today’s hyper-hypersensitive culture where there’s a real bloodlust for cancelling people and a deep, deep desire to be offended. shane gillis is as solid a dude as they come, and you don’t have to look very deep to see it.