In light of what we see today, this is hard to believe. However, as a result of Castro’s death, I accidentally became interested in the history of this fascinating island and the more I discover, the more shocked I am at “the path” that Cuba has taken. One of these reasons is provided below by Victor Bulmer Thomas in his Economic History of Latin America since Independence. Now, Thomas uses a different approach than the commonly used Maddison data (he believes the assumptions are too heroic). He uses indicators correlated with GDP per capita to fill in the gaps and he finds that Cuba was generally richer than the United States for most of the 19th century (see below):
Now, I am not convinced by the figure Thomas presents. However, I am also skeptical of the levels presented by Maddison (where Cuba is roughly 60% as rich as the US in 1820). In between are some more reasonable estimate (see this great discussion in this book as well as this discussion by Coatsworth). Moreover, there is the issue of slavery which distorts the value of using GDP per capita because of high levels of inequality (however, it distorts both ways since the US was also a slave economy up to the Civil War).
Nonetheless, this tells you about the “path not taken” by Cuba.