I used to do something like this occasionally with my chud cousins. I'd say stuff like leftists stole feminism from conservatives or that Republicans are actually leftists in secret, so they're all voting for leftists. I'd call him a socialist for stuff like doing food drives at his church.

If my idiot cousins work as test subjects, this strategy tends to have the effect of forcing the chud deeper and deeper into a right-wing corner to protect their credentials until they eventually get so frustrated they'll just drop the mask and start talking about killing gay people on the spot and endorsing Christian fundamentalist nationalism. They'd get so pissed off about any accusation of being on the left all they would know to do is say stuff they assume a leftist would never say

I think the smarter or more plugged in internet right-wingers will just get confused and disregard what you're talking about.