What if the pendulum swings back and not only does he de-transition, but he becomes Ultra Chad and starts pumping iron?
As funny and cool as that would be, I sadly doubt it.
In my personal opinion, Chris might be one of the few troon lolcows who might actually have some kind of gender dysphoria, albeit nobody here can say for sure due to Chris's autism, low intelligence, and general incoherence making it far more difficult to tell if he's a troon faker or actually dysphoric.
Unlike ADF or the Rat King lolcows who are all either painfully obvious fetishists, SJW identity opportunists, or a mix of both, Chris is not a clear-cut case of a transtrender.
Unlike ADF or Jake Alley, he actually attempts to look feminine and pass, although he fails miserably at it.
Still, you can tell that Chris actually puts in some kind of effort and before the dimensional merge stuff kicked in, he could still pass as an older homeless woman from a distance since he just wore old granny clothes he got from either Barb's closet or Goodwill instead of decking himself out in cartoon princess stuff.
Also, there's a lot of other evidence at his troon phase being inevitable.
In the Classic days, Chris was a raging misandrist who thought any male who wasn't his father was a jerk, and his homophobia really only applied to gay men (and was likely due to his conservative upbringing) and a lot of his interests were either stereotypical girly interests or childish interests (or both)
He was into My Little Pony years before the brony fad kicked off, and while that was due to Megan's influence, any other guy probably would not have gotten into MLP just because their crush liked it.
Unlike Sailor Moon, which had a sizable male fandom even in the 90's since it was more action-oriented than most girl shows at the time (and let's face it, a lot of boys in the 90's probably had a crush on the Sailor Scouts) there wasn't much of a male fanbase for My Little Pony until 2010.
Also, he was an adolescent in the late 1990's, an era well known for "extreme" edgy pop culture aimed at teenage boys and young men.
Chris's middle school and high school years were the same era that gave us Resident Evil, Rob Zombie, the Attitude Era, Vampire; The Masquerade, The Matrix, and black trenchcoats being unironically cool and yet Chris was mostly into the same trends from his childhood years (as well as the then-new Pokemon fad)
Even his tastes in music back then was mostly late 90's/early 2000's bubblegum pop that was aimed at teenage girls.
Chances are most of the boys in his class at that time would have been more into rock, rap, or metal (maybe some of the more crossover-friendly country acts given the location)
Part of what made his insistence on being a straight manly man in the Classic years so funny was because of how obviously effeminate he was.
Plus, he got into the Tomgirl stuff entirely on his own and at a time when transgender issues weren't really a thing in the media like they are now. Any troll interference regarding the Tomgirl stuff was basically limited to a single vaguely worded comment from Jackie, and I doubt the trolls intended Chris to start cross-dressing based on that comment alone (though they certainly had a field day when he did)