Trade with Cuba is not free trade
The Heritage Foundation has published its annual Index of Economic Freedom. Cuba is ranked 176 out of 177 countries in the index. Only North Korea is less free economically than Cuba. This gets to the crux of my argument against the Libertarian view that free trade frees people. Trade with Cuba is not free trade. It's trade with a Cuban state that operates the second most restrictive economy in the world.
Cuba scores far below world averages in most areas of economic freedom, and its economy remains one of the world’s most repressed. The foundations of economic freedom are particularly weak in the absence of an independent and fair judiciary. No courts are free of political interference, and pervasive corruption affects many aspects of economic activity.
As the largest source of employment, the public sector accounts for more than 80 percent of all jobs. A watered-down reform package endorsed by the Cuban Communist Party in April 2011 promised to trim the number of state workers and allow restricted self-employment in the non-public sector, but many details of the reform are obscure and little progress has been observed. The private sector is severely constrained by heavy regulations and tight state controls. Open-market policies are not in place to spur growth in trade and investment, and the lack of competition stifles productivity growth.
It's a captive nation, imagine trading with a prison. You can make deals with the warden and the guards but the prisoners will only see the benefits that their captors allow them to see.
By the way the US was 10th on the list, losing ground once again.