Ask Admiral William James Crowe, Jr; after being caught smoking a Havana cigar in the embassy, he was accused of breaking his country’s strict embargo on all things Cuban:
It would be far more effective to just develop a plant disease or a modified insect that could attack Cuban tobacco crops, release it across the fence at Guantanamo, then sit back and wait for the Cuban economy to collapse.
But, of course, you need to be careful that it doesn’t get accidentally released in US tobacco fields. Or delibrately released, by Cuba, after they figure out what happened. And that’s a pretty big ‘but’. Enough that even Hitler didn’t use chemical or biological weapons on the battlefield in WWII.
But the US has used planes to spray herbicides over hostile territory in the past, for example in Colombia and Vietnam. Possibly the planes aren’t as vulnerable as you think.
Well, Vietnam is 3 times the size of Cuba, Colombia is about 10 or 11 time bigger. And the planes were flying in from land right next to there, rather than from across 90 miles of ocean. Just the chance of finding these planes would be much lower.
In Vietnam the planes were spraying large areas of jungle in territory controlled by a US ally. They were not spraying where the enemy was. In Columbia the Columbian government provided attack helicopters to keep people from shooting the planes. In both areas they were spraying peasant farmers and rural villages and left lots of evidence behind. In neither of these cases was the spraying done at night over hostile areas in secret.
Regarding the virus approach: tobacco mosaic virus is a reasonably harmful, common tobacco pathogen. It could be dispersed from a much higher altitude from fast flying planes (or drones nowadays). It then propagates itself. Extremely easy to produce in huge quantities. Persists long enough that you don’t need to hit an area every year. I doubt the Cubans can afford to do crop rotation, which would make an outbreak persistent.
Plus you’d ruin the pepper and tomato crops and that would definitely get the average Cuban’s attention.
Cuba shot down a U2 50 years ago. High altitude won’t be a problem.
It was Russian advisers, was it not?
To tell the truth I don’t recall. I do know that Gary Powers and the one over Cuba were brought down by SA-2s which is very old technology now.
According to the William F. Buckley novel, it was done on purpose so that Eisenhower wouldn’t have to attend some conference or other.
Keep in mind that even the lowly U-2 of today is not the same plane of 1960. The last one was delivered in 1989. And like the B-52, frequent updates occur. So a lot of stealth technology has been presumably added. It’s like the Ship of Theseus with high tech alloys and jet engines.
And the U-2 is hardly the only (manned) option.
Shoot, you could send a small rocket over the island during a thunderstorm (on a course that would have it land in the drink), set off some small discharges to release the virus dust over the island. The rest goes to Davy Jones.
All of which are immensely more plausible than a low and slow crop duster.