In the 1950s, in terms of GDP per capita, Cuba was at the level of Puerto Rico, Costa Rica, Mexico, Portugal, Greece, and Spain (!), and considerably above Brazil and the Dominican Republican.
Today, it is far behind all of them, having dropped from 20% of US GDP per capita then to just slightly more than 10% today.
So it’s pretty clear that its economic record under Communism was pretty disastrous, though not a complete outlier in the region. The two other big underperformers are Argentina and Haiti. Argentina is somewhat infamous as the only major country to go from First World to developing country living standards over the course of the 20th century, plummeting from 70% of US GDP per capita to less than 30% by the turn of the millennium. The other example is Haiti – that slice of Sub-Saharan Africa in the Americas – which has declined not only in relative but absolute terms over the past half-century.
That said, when Castro made the decision to adopt the Marxist-Leninist model, it had not yet dawned on the popular consciousness that central planning was fundamentally inefficient, so one can’t be too judgmental about that.
The Cuban economy was massively subsidized by the Soviet Union during the Cold War, which bought its sugar at artificially inflated prices – though much of that money was in turn frittered away by the Cubans in their African adventures, which did not benefit ordinary Cubans in any way apart from in the form of some vestigial goodwill from foreign progressives. Once those Soviet subsidies dried away from the late 1980s, the Cuban economy started collapsing. (In 2014, Russia wrote off a whopping $32 billion worth of Cuba’s debt).
Ironically, as a result of that, they became the world’s only “sustainable” country, combining high human development with a low ecological footprint.
That said, high human development was not a specifically “Communist” achievement, since it would have happened anyway if perhaps marginally slower. Pre-Castro Cuba was hardly the feudal, illiterate dystopia of Communist propaganda. Its infant mortality rate in the early 1960s, though not quite First World, was nonetheless at almost the exact level of Spain or Italy, and lower than in the rest of Latin America – almost three times lower than in Mexico, Brazil, and Chile. The literacy rate was close to 80% and would have converged to 100% naturally. In this respect, Cuba’s achievements in healthcare and schooling become a great deal less impressive.
The Cuban regime was pretty mild in its level of repression, by Communist standards. The Cuba Archive, which documents deaths and disappearances “resulting from the Cuban revolution,” claims 10,723 victims. However, it also includes the victims of the Batista regime, which might have concentrated as much political violence into a single decade as the Castro regime did over half a century; and its also worth remembering that some proportion of executions even in the most tyrannical states will be genuine criminals. The Black Book of Communism claims a figure of 16,000 executions in Castro’s Cuba, but should not be taken at face value given its propensity for exaggeration. So in per capita terms, Castro’s Cuba seems to have about as politically violent as Pinochet’s Chile or the Argentinian junta (though diluted over a longer time frame), and far less violent than the mainstay Communist regimes of Eurasia or for that matter the US-backed Contras in Nicaragua.
In the longterm, perhaps the most damaging effect is that many of the brightest and most enterprising Cubans have emigrated. Communism is a veritable IQ shredder. Could a post-Castro Cuba still produce a Capablanca?