Somehow I find it difficult to see the Venezuelan Navy as a great threat.
What are they going to do, shell San Juan?
If they do, the US Navy will destroy them in about an hour.
Yet another example of the old saying “a fool and his money are soon parted”.
There are two vital sea lanes straddling Puerto Rico - the Mona and Virgin Passages. These are important approaches to the Panama Canal. He could slow worldwide trade to a crawl if he were to blockade shipping there alone.
My bet would be ships...I would also bet that our ASW guys would have a BIG surprise ready for them.
How about sinking an oil tanker at the entrance to the Panama Canal? Anonymously, of course. We're not talking about a mentally stable guy here. He could do enough mischief with one or two anti-social acts to throw the economy of the western hemisphere into quite a tizzy.
Of course, he'd pay for it in spades. But never depend on a lunatic to pay much attention to the things that might deter a sane person.