I read an article a while back on GA in Cuba pre-Castro, with lots of photos. It was once a popular place for GA, and a lot of those planes were used by those who were lucky enough to escape, overloaded with their families etc. I wonder how they transferred them to N-register, presumably without Cuban cooperation to cancel their existing registration and issue an export C of A?
I've worked with any number of people who escaped the east block, and it seems most of them did it through vacationing in Yugoslavia. One by defecting from a sports team playing in Italy.
It's great to see many Yak 50s and 52s locally, now being flown by owners who fuss and take care of them. The Yaks eventually escaped too, but had to wait until the 90s or so.