he was kinda cool in some ways but when things got tough his project too quickly resorted to some level of chaotic vanguardism and violence to pull through and manage stuff. Scale that up to the complexity and issues the USSR project had to deal with and you can quikly see he was far from a "better alternative than the bolsheviks that they crushed"

There's a story I always talk about that I think is the perfect encapsulation of his being a loser:

In June 1926, during a meal with Alexander Berkman and May Picqueray in a Russian restaurant, Makhno met with the Ukrainian Jewish anarchist Sholem Schwarzbard, who went pale upon seeing the [fascist] Ukrainian nationalist leader Symon Petliura walk into the room. Schwarzbard immediately informed the Batko of his intentions to assassinate Petliura, in revenge for the pogroms carried out in the Ukrainian People's Republic, during which some of his family members had been killed. Makhno attempted to dissuade him but the deed was carried out anyway, with Schwarzbard's subsequent trial bringing to light a trove of documentary evidence on the pogroms in Ukraine, exonerating the assassin.