If I had to guess, he was actually in the military, and now he's a payrolled spook who is supposed to get into various groups that are considered to be a potential threat, whether it's Antifa, or "Right Wing Conspiracy Theorists" or wherever they send him. They probably send him out to find out what the locals are planning, who the hot-heads are, and report back. He's a plant or a narc or whatever you want to call it. I don't know where he would be getting money to fly around all over the place and go get arrested in all of these different cities otherwise.
If I had to guess, he was actually in the military, and now he's a payrolled spook who is supposed to get into various groups that are considered to be a potential threat, whether it's Antifa, or "Right Wing Conspiracy Theorists" or wherever they send him. They probably send him out to find out what the locals are planning, who the hot-heads are, and report back. He's a plant or a narc or whatever you want to call it. I don't know where he would be getting money to fly around all over the place and go get arrested in all of these different cities otherwise.
Edit: Sort of a "Timothy Leary" type character.