Oddly enough, I think of all the major lolcows, Chris would be the one least likely to de-transition.
He was already kind of experimenting with transgender stuff during the whole Tomgirl phase he went through and the Tomgirl stuff was both well before the troon fad and was something Chris started doing entirely of his own volition with little to no manipulation from the trolls.
Even in the "Classic" days, Chris showed signs of possible gender dysphoria, although his autism and low intellect do mask some of the obvious and traditional symptoms of gender dysphoria somewhat.
He was a raging misandrist back in the Classic era and had a lot of stereotypical girly interests (he was into MLP years before bronies were ever a thing) and a lot of his homophobia and insistence on being a male at the time was likely due to Bob's influence.
Bob was dying when Chris became a Tomgirl and after he died, Chris became more committed to cross-dressing until he finally jumped the chasm and trooned out.
Also, Chris is probably the only transgender cow whose life improved (albeit marginally so) after going full troon and for a while, seemed a little happier as a tranny and even made some friends and acquaintances with the local LGBT community in Charlottesville.
His life was still a complete wreck, but it was slightly better than before he trooned out, at least until the Idea Guys entered the picture and massively fucked with his head.
