I’ve never read any Jack Kerouac, but supposedly he ended his life as a devout Catholic, and he was extremely anti-communist, apparently a great admirer of Senator McCarthy.
Had he not thrown his life away with booze and benz, Kerouac was on the path to writing the sort of book Wolfe was working on, but the vantage of a disillusioned insider.
I was exposed to a hearty dose of Ginsburg, Keroac, Ferlinghetti, and the likes, as a Literature major. As a returning Vn era veteran, I could identify with the insanity, rebellion. Read “Howl” by Ginsburg if you dare. It is pure counter culture. Spawn of this generation of degenerates include Bob Dylan, Dave Van Ronk, Leonard Cohen and many other poets and musicians that took root in the early 60’s. It was a wild and crazy time and place. Keroac must have had a few moments of clarity in his later years to adopt a political posture as you describe. I always figured them to be to self-centered and self-destructive to subscribe to anything but anarchy. Interesting topic.
Kerouac’s On The Road is four bucks at Amazon Kindle. Read it in the late 50’s and again last year. It still holds up. It’s rumored to have been the basis for the Route 66 TV Series. Kerouac’s Big Sur, on the other hand, is thoroughly depressing, and an inside view of cracking up.