Masada was crushed in a brutal invasion. The 21st-century US Military is phenomenal at invading countries (look at the rapid falls of Iraq, Afghanistan, and ISIS, we are substantially worse at occupation but that’s besides the point). If we wanted to crush Cuba we would have done it the second communism fell.

The reason we still have an embargo on Cuba is because pro-embargo Cuban-American refugees are a huge minority of a swing state, and sending a child away from his abusive father to Cuba literally cost the Democrats the 2000 election (incidentally leading to at least 2 of those 3 invasions). Arguably, a stupid technicality like that is worse than if it was a Masada-type situation, but what can you do

The families on Masada killed themselves before the Romans broke in with their constructed ramp.

And those who do submit can look forward to being more like Haiti.