Bit of a madman, wasn't he? Where did it all go so wrong?

Bit of a madman, wasn't he? Where did it all go so wrong?

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gci-icg.org/english/ukraine.htm
books.google.com/books?id=QBTLrRnq6MUC&pg=PA317&lpg=PA317&dq=bookchin Makhnovtsy&source=bl&ots=vxHz_sAbyk&sig=9HEV4oEEDV16rZVpCwSqL07UaoI&hl=en&sa=X&ved=0ahUKEwidvObh84vSAhVS9mMKHTszBXkQ6AEIMzAE#v=onepage&q=bookchin Makhnovtsy&f=false
theanarchistlibrary.org/library/ted-kaczynski-the-truth-about-primitive-life-a-critique-of-anarchoprimitivism
libcom.org/history/kontrrazvedka-story-makhnovist-intelligence-service-vyacheslav-azarov
marxists.org/reference/archive/makhno-nestor/works/1925/12/revolutionary-discipline.htm
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He trusted a Bolshevik.

he fucked up with inflation and secret police

...

there's your problem

"The Makhnovist's Insurrectionary movement aspires to create from the revolutionary peasantry, an organized and real force, capable to fight the counter-revolution and to defend the independence of a free region."
As one can see, the social-democrat idea of socialism in only one region, that will later become with Stalin and Boukharin, "Theory of socialism in only one country", was as dear to Makhno as to the Bolshevik governmental right wing.
The worst, it is that a revolutionary leader as Makhno stayed captive of the "stalinist" prospect before "stalinism", and that, in the heat of worldwide revolutionary wave, in a time where from Berlin to Patagonia, from Bombay to Mexico, from Budapest to Toronto, the proletariat struggled for the one worldwide revolution!
The limit of the insurrection in Ukrain will find thus, beyond objective problems of relation force in this period, new agents in the lack of generalization of the revolutionary war. The "anarchists-communists" in Ukrain had perceived and criticized the weapons in their hands, the refusal of the generalization of the revolutionary war through the agreements of Brest-Litovsk, but they have been incapable to understand in what the generalization of the revolution passed also through the as well dictatorial and violent struggle against Economy, against Value.

gci-icg.org/english/ukraine.htm

pretty based actually. if he had a major flaw, it was that he did not know how to apply his libertarian principles to industrialized cities. Probably would have done better had he not been so willing to assist the bolsheviks.
books.google.com/books?id=QBTLrRnq6MUC&pg=PA317&lpg=PA317&dq=bookchin Makhnovtsy&source=bl&ots=vxHz_sAbyk&sig=9HEV4oEEDV16rZVpCwSqL07UaoI&hl=en&sa=X&ved=0ahUKEwidvObh84vSAhVS9mMKHTszBXkQ6AEIMzAE#v=onepage&q=bookchin Makhnovtsy&f=false

I mean, the fact that he implemented anything remotely socialist when his entire experiment was conducted in the middle of a multiparty civil war is admirable

He deserved it tbh.

There were a number of internal problems within the very structure of the Free Territory that would have likely lead to a decline in the ideals they were supposed to stand for and perhaps lead to their collapse, but most of those problems were long-term issues that really didn't play that big of a role in the Free Territory's historical failure to survive. The biggest problems were undoubtedly external.

There was the first problem that, unlike other groups like the Bolsheviks, his ability to conduct pre-revolutionary agitation and organization was pretty limited: he became involved in anarchism in 1906 while quite young and was in prison on a life sentence by 1910. This did not even afford the limited luxuries of being in exile where one could still remain partially in contact with revolutionaries still in Russia and be able to study while waiting. He was released during the February Revolution, which left him ~8 months to prepare a militant revolutionary force. Part of that work was already done and at the ready through the work of those aforementioned anarchist organizations, but there were numerous communication issues that meant they weren't as easily capable of collaboration with one another. Makhno was not really a national figure at that point, though he came to be decently well known regionally in Ukraine which aided his cause. In other words, the scale by which he was able to organize a movement was considerably limited.

The Free Territory, once established, also ran the problem that it could not realistically fight both the Reds and the Whites due to the limitations on its scale: it required good faith on the part of the Bolsheviks to leave them be while the Whites and other forces were pushed out. This was admirable, but also meant that they were wholly unprepared to deal with later opposition from the Bolsheviks.

Longer-term you had the problem that, while Makhno was certainly committed to the anarchist cause, the actual army he was leading was threatening to turn into a de facto vanguard over the soviets that were otherwise governing the Free Territory at the time (secret police and such). Also he was pretty staunchly against most forms of industrialization, the prime innovation among them being investment into railroads.

His goals were admirable, but there was almost no situation where it would have succeeded long-term unless the Bolsheviks were willing to not only let them be, but also probably work with them to provide goods and such that the Free Territory had no real way of providing for itself long-term. Nobody in the Bolshevik leadership besides perhaps Lenin was particularly interested in seeing the Ukrainian socialist experiment continue either, so the final confrontation between the two forces was inevitable.