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.