What would be the easiest - but significant - dictatorship for a U.S. billionaire to start?

Looks like someone’s already done it. William Walker was a rich guy who decided there needed to be more English speakers in the America’s, so he just up and invaded Mexico. And Nicaragua.

Eh, it happens now and then.

The most successful guy to give it a go was French mercenary Bob Denar. In 1975-1995 he staged a number of coups in Comoros and spent a good chunk of time basically ruling the place (a figurehead officially ruled, but it was Denard who ran the military and therefor called the shots.

Less successful was the Wonga Coup (there is a great book about it) lead by Simon Mann and famously partially funded by Margaret Thatcher’s son. It ultimately failed for a number of reasons, from unprofessional planning, incorrect assumptions about the backings of major powers, poor coordination during the actual coup effort, and a general excess of hubris.

From all this, we learn a couple things. Islands are good targets- you don’t have pesky neighbors who want in on the action and the opposition doesn’t have anyplace close to go hide out and regroup. You will need to be a bit smarter than Mann, and realize that you can’t just wander Africa with an arsenal and not get called on it. Even a billionaire cannot possibly bribe everyone who could potentially get in the way, so you are going to have to convince some important people that they are on your side.

Finally, you need Western powers behind you. France (or Britain or whatever) will support you if it further their foreign policy goals, and will crush you like a fly (or arrange for your plane to crash) if you don’t. These days, with the end of the “communist threat,” the former colonial powers have become a lot more hands off and are much less likely (but not entirely unwilling) to get involved in this sort of thing, But they are still a- perhaps the- deciding factor. You best bet would be to perhaps piggy back on the “Islamic threat.”

Well, the solution to that would be to install blacks in positions of leadership along with whites. You realize that there were more blacks than whites in the Rhodesian military. I’m not talking about guys stuck on shit details, digging latrines and peeling potatoes. There were blacks in the most elite fighting units like the Selous Scouts and Grey’s Scouts. Plenty of them were pro-Rhodie and anti-ZANU.

Put a face on the new government that was representative of the people to be governed.

I am positive this situation could be worked out. The average person in Harare is more concerned with having clean water, decent food, and personal safety, than they are with any political ideology. Give them what they need, and they will love the people giving it. In this way they are much like every other person on earth.

Side-stepping the Rhodesia debate for a moment, I’d think that a Billionaire Supergenius looking for somewhere to take over and run as their own country would probably be advised by their Number Two/Distinctive Henchman to be looking at one of the numerous tiny Pacific Island nations- places like Tuvalu or Kiribati.

The problem is that even though they’re small and isolated, someone like Australia or New Zealand (or possibly even the US) might decide that they can spare a couple of ships and a few Hercules-loads of troops to sort things out if the “Coup” lasted any longer than a week or so and the locals were complaining about the new management.