Territorial Accession

What would be the easiest country to get? Like convincing poor governments to join a relatively richer one with lots of territory and resources.

Pacific island nations would seem to be the easiest in many respects: tiny populations, isolated, of no consequence geopolitically, and often abysmal economies. Nauru would be a particularly good bet, since essentially the entire population of the island is dependent on welfare. I could certainly see Nauru or plenty of other island nations willfully joining a foreign government, or just being steamrolled by any first-world country since they have no defense forces.

In 1870 President Baez of the Dominican Republic, then called San Domingo wrote to President Grant of the uSa asking to be annexed. Grant sent a group to travel the country and stusy the idea. The study group sent 1 year travelling around and recommended that yes US should annex the Republic. It was put before the US Senate which turned it down by one vote. One of the reasons for doing it was that the Civil war had just ended and a place to send all those newly freed slaves was on a lot of peoples’ minds.

But for precisely those reasons wealthier states with lots of resources and territory have no particular interest in corporating these states. They will be a net drain on resources.

By virtue of their location, they could conceivably have a strategic value. In the past this might have lead wealthier nations to, e.g. occupy and administer them them as colonies or protectorates. Today, it would probably be easier simply to enter inot a bilateral agreement allowing the wealthy state to maintain military facilities (or whatever) in the poorer state. Complete incorporation into the domestic territory of the wealthy state would probably cost more, and both then and now usually goes beyond what is needed to secure the desired strategic advantage.

Wasn’t there a movement a couple of years back where the Cayman Islands were trying to join Canada as their eleventh province?

That’s true, and that’s also what has happened with a lot of these states. But just because they’re not particularly good territory doesn’t make them not trivially easy to conquer.

Sure. But being trivially easy to conquer is not a problem if, in fact, nobody wants to conquer you.

Plus, defeating and a state is one thing; long-term occupation of its territory, if that’s not what the locals want, is another. Simply because it would be trivially easy to defeat state X in battle doesn’t mean that it would be trivially easy to incoporate it as part of your own territory. The initial invasion may be only a tiny fraction of the the total costs, both financial and political, of incorporating the territory.

Santo Domingo.

Pretty sure we figured that out in 2003-2011.

Not really true if you’re sufficiently ruthless. Just kill the existing inhabitants and you’re set.

I think you are thinking of the Turks and Caicos islands.

There are quite a few island nations around the works who, like the Turks and Caicos Island are remnants of the old British Empire. After WW2 it became an embarrassment to rule other people’s countries and the British set about divesting them as fast as they could.

Some chose to be semi independent and are currently autonomous overseas territories. This is a pretty hand-off form of colonialism as the main role of the British is to be the ultimate legal authority through an appointed governor whose main role (like that of most presidents) is ceremonial. Someone has to open the hospitals and hand out the medals.

Fishing rights. France has one of the largest (maybe even the largest, can’t remember) exclusive economic zone in the world thanks to the possession of a variety of islands scaterred around the oceans, for instance.

Even the smallest islet comes with a very large EEZ.

Note that in the case of Turks and Caicos in 2008, the colonialism became suddenly a lot less “hands off”, when the UK suspended self-rule in response to systemic corruption of the local government.

Some of those island nations are expected to be totally underwater in a couple decades or so (depending on how fast Greenland and West Antarctica melt), so you could probably pick them up cheap. Just be prepared to relocate their entire populations soonish.

Including, I learned here just a few years ago, off the coast of Canada: Saint Pierre and Miquelon - Wikipedia