The "Bay of Pigs" in 1961 was a total fiasco. We recruited some Cuban exiles and then sent them on a suicide mission with no air support. What was JFK thinking? And of course, he went and pretty much made the same mistakes in Vietnam (exacerbated by Lyndon Johnson).
The Cuban Embargo is a total failure as well. If anything, the embargo has enabled Castro to remain in power all these years. It forced him to develop close ties with the Russians (then Soviets) and brought about the Cuban missile crisis, which could easily have resulted in WW3. The embargo has enabled Castro to turn his people against the USA while keeping them in poverty. If you notice, everytime the United States considers relaxing the embargo, Castro does something blatant and provocative to force us to take it off the table. You see, the last thing Castro wants to see happen is for us to lift that damned embargo. For as soon as we lift it, Cuban goods will flood U.S. markets and U.S. money will flow into Cuba. Castro will try to stop it but even a brutal dictator like Castro can't stop the law of supply and demand. The Cubans will find some way to get their products into America once there is a demand for it. (In fact, even with the U.S. embargo, anybody who wants a Cuban cigar in America can still find one.)
Castro is 76 and pretty much at the end of the line. Even his heir-apparent brother Raul is now 71. They could feasibly last another 10 years but I doubt Raul will be able to hold things together once Fidel goes. If we lift the embargo immediately, the process will speed up rapidly. I don't think Castro or his brother will last a year once the embargo is lifted.
Just what Cuban goods would flow into US markets? Nothing is flowing into Canadian, British or French markets, and they have no embargo. As far is I can tell, Cuba has nothing to sell, they can't produce enough of anything for domestic consumption.