I would say its much more simple. Hes a cynical, narcissistic, and jawdroppingly hypocritical opportunist when it comes to jumping on social bandwagons...but he is also an out of touch and perpetually angry boomer.
The latter point is important since it explains his current mix of anti trans demagoguery and cringy "FFAAAAAACK YEW DRUMPFFF! FACK YEW GOOBERGRAPE!!!" tantrums. Basically he jumped on the OG proto-SJW bandwagon way back when, which at the time was just straight up radfem "sacred womynhood must be protected from the vile men who seek to impersonate us despite not having holy vaginas and saintly menstruation" (wish this was hyperbole but...nah its actually underselling the creepyness of it all)
Despite the fact that he threw this aside the moment it became convenient for him to be a "LOL SILLY WAMMEN! LOOK AT HOW EDGY I AM HEIL HITLER LOL!" style comedy writer for a decade or so, when it came back in vogue in his circle of affluent media people to be an SJW he immediately jumped on this bandwagon both for asspats/protection from REEE mobs against him for his old work, and to take his middle aged hasbeen anger out on easy targets, and assumed that nothing had changed since the 80s and that everyone still hated trannies despite this being utterly in contradiction with modern SJW dogma.
Ofcourse when his anti trans spiel got to the point where he was unironically outdoing the kind of things we here say for shits and giggles, enough blue checkmarked SJWs were able to get over the "dont attack our own team plz, especially if they hate who we tell them to hate" rule and quietly began asking him to be a bit more chill....which caused him to go absolutely apeshit with rage about how an evil "professionally woke" conspiracy was after him and his pure and noble defence of womyn, and he started doubling and tripling down on the unironic "trans people are subhuman scum who need to be put in camps" schtick.
The reasons for this seem to be entirely to his own ego and tard-rage against anyone disagreeing with him, which has only intensified since then to the point where it straight up broke his mind to the point where he spends every day on twitter screeching about how trannies are coming to steal the vagina gold and rape all girl scouts, while occasionally punctuating it with "I SAID GAMERGATE WAS BAD! I AM A HERO OF THE PROGRESSIVE MOVEMENT!" whining when he sees another checkmark attacking him.
With regards to Jake however, this really does illustrate how utterly dishonest and conditional his apparent fanaticism against anyone who is deemed "offensive/problematic" has always been. Linehan has been spewing this shit for years now, and jake was more than happy to ignore it and fawn over him solely because it made him personally feel important.
EDIT: huh.....after quickly checking this chucklefuck's twitter, it seems that as of today he has a new group to throw perpetual tantrums about...
...us.
https://twitter.com/Glinner/status/1063786124144009216
