the majority of insurgents dont succede. Have any of the dozens of the anti-Indian seperatists and communists groups succeded? No. What about the tamil tigers? How did Che end up? Did the Forest Brothers succeded in driving off the Soviet Union?
The vast majority of insurgents will die alone. People just glamorize it because they don't make it to the frontpage of the news.
usually these groups control territories for a long time until the regime waits them out, then they literally die of old age. this was largely true of the indian insurgents (who still exist btw) and the forest brothers. che died because he bit off way more than he could chew, he was very successful in cuba.
if you want an example of a "decentralized asymmetrical insurgency", then there's thousands of random bumfuck islamist and wignat groups to choose from. moreover street gangs continue to operate all the time regardless of police interference, and that's largely because it's still economically advantegous to do so given the sheer amount of capital to be had via the drug trafficking and distribution trade. don't even get me started on the actual cartels themselves. all this to say that yeah, some don't succeed, but counter-insurgency/counter-terrorism really isn't anywhere near as easy as just "arrest them all lol", if it was then we wouldn't have had a 20 year GWOT lol.
Fundamentally it's political. There was a lot going on in Cuba that made it possible for an insurgency to succeed that involved the politics of the country. It wasn't just the rebels inna Sierra Maestra but unrest with the urban population. It's too complex to get into and I don't even know a lot about it, but I believe there have been historians who have written books about all that. Che was a narcissistic and suicidal personality who couldn't deal with sitting around in boring meetings after they won, so he ran off to try to make revolution in Congo and Bolivia and it just didn't work at all, and then he was killed. He was going to end up like that one way or another. It's kind of a historical accident that he became this big hero because they won in Cuba, but in some slightly different circumstances he would've joined another one of these rebel groups in Latin America at the time, would've been killed and nobody would've ever known he existed.
It's interesting to read about left-wing groups in the U.S. in the late 60s who tried to cosplay as Che like the Weather
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