Fidel as a "success" might be a toss up and since this is a Miami board, it might be of interest to discuss.
Fidel Castro's father was one of the wealthiest slave-owners in the world when he died. Fidel grew up on a plantation with over 400 Haitian slaves. Fidel and Raul both inherited close to what would be tens of millions of dollars today each when their father died and they kept the plantation running for years. They even grew it by confiscating everyone else's sugar farms and bringing in more Haitian slaves. Sugar prices also boomed in the 1950s and 1960s which led to Fidel's and Raul's rise to power. They would eventually run the plantation into the ground and the Cuban government took it over in the 1980s. That's bad. A dictator forfeited an asset to the state. A dictator should be taking assets from the state or at least holding on to their own assets. Furthermore, sugar exports didn't really decline until the 1990s. So the might have run their only real asset into the ground despite stable commodity prices.
After inheriting everything from his father, what would his net worth need to be when he died to be labeled successful? Should that be the question?
Fidel claimed that he was worth $900 Million, but we are finding out that he might be confused about the meaning of the word "net worth". Net worth means Assets less Liabilities. Books have been written about Fidel's wealth claiming he owned over 20 mansions and blah blah blah. But after his death we are finding out that those mansions and yachts were owned by the government of Cuba and Russian oligarchs. His children did not inherit one physical asset.
If you look at his children and family today (excluding Raul), no one lives anything close to a lavish lifestyle. Only his sister, Juanita, seems to have a comfortable life. She also started and sold a business in Miami to CVS pharmacy which would have most likely netted here a nice payout.
It could be easily argued that Fidel and Raul squandered their family fortune to become political puppets and life-long tenants to Russian oligarchs, leaving their children nothing.
PS: Fidel got Cuba out of Sugar exporting to get into dairy as he thought a self-sufficient dairy program would be a substitute for foreign trade. Dumb.