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Question

Premise

I am trying to piece together a world where a country has two territories. One territory is very far away from the other. Between the disjoined lands are long stretches of hostile enemy territory. Having distant territories is hardly a novel affair; the Romans, Persians and Ottomans boasted vast ones. However unlike many of such empires, the country in my world does not have a continuous slew of land. For a real world historical analog, we can look at the former state of East Pakistan:

enter image description here

It is clear from the map that the territories would face numerous logistic and strategic complications. East Pakistan was almost 2000 miles away from West Pakistan, and it stands to reason that this geographic dimension added to the cultural and political turmoil that ultimately drove East and West Pakistan apart during the Bangladesh Liberation War.

East Pakistan is certainly a decent starting point, but is by no means the best case scenario for a distantly disjoined country. One could arguably assert that the military presence West Pakistan had in East Pakistan ultimately worked against them. Allegations of genocide along with other complications led to the demise of East Pakistan in less than 20 years. I would like my world's disjoined state to last much longer.

Question:
What is a viable military strategy for a disjoined state to secure sovereignty in the long run?

Further Clarifications

Terminology: I will refer to the larger, main territory simply as "the state." While I will refer to the far flung territory as "the isolated territory"

Of course the state is larger and stronger, the isolated territory is smaller and weaker but not a pushover. The isolated territory has enough supplies and troops for the short-term, but will not survive prolonged warfare or lengthy attrition

The isolated territory is able to be self-sufficient in terms of sustenance, but it is landlocked and faces logistical challenges

Rivers from the isolated territory reach the sea.

Between the state and the isolated territory are roughly 2,000 miles of hostile enemy territory (depending on route)

There are a total of 3 neighboring states, all of which are hostile

Military strength is roughly equal between all 4 states

Diplomacy has failed, alliances could not be forged, deals could not be struck

The isolated territory's narrative is largely out of scope, but you may assume it's existence is rather new

The loyalty of the isolated territory to the state is absolute. However, slight cultural differences exist.

Era: Roughly middle ages (knights on horseback and the like)

Here are maps: [White = disjoined country] all other colors are hostile.

You may generate the original
here

Seed:1492628839

enter image description here

The state has so much island and sea access, it likely has a strong navy presence. Does the landlocked country have river access to the sea that the state could use? As for protection, does blue really need to be behind red? Because if the state could threaten a multi-sided war to split up enemy forces it could simply use that threat to keep enemies from attacking, "you take my disjointed area I take your capitol and important economy area's". But that kind of threat is impossible against blue atm. Without politics blue can just take it and say "what you gonna do, bleed on me?" — Aug 22 at 11:44
@Demigan Excellent concerns, some of which I struggled with too, they may remain unresolved for a while. We can assume there are rivers leading to the sea from the isolated territory. I will edit for that. — Aug 22 at 11:49
Ummm French Guinea? Reunion? French Polynesia? So the answer is "speak French". Or at least send a lot of your criminals to that land. It worked for a time for Australia. — Aug 22 at 14:23
Can it be a vassal state, rather than a coequal part of the larger state? — Aug 22 at 17:52
This setup was true for several colonial powers in the 19th and early 20th centuries. — Aug 22 at 18:26

Willk 85.6k21170372 · Accepted Answer · 2018-08-22 13:41:56Z

Play off blue against red. The parallel is Mongolia.

http://www.citiesandplaces.com/where-is-mongolia-located-mongolia-map/

Mongolia is a landlocked buffer state between Russia and China, and before that between the USSR and China. It serves as a buffer, reducing the shared border between these two powers, curbing immigration and reducing tensions. Should one of the bordering powers make a move it would be seen as threatening to the other.

In modern days there is even more similarity to your situation: the involvement of a distant power (the US) in Mongolia bringing wealth and resources. Neither of the bordering powers mind this much as both see it facilitating the action of Mongolia as a buffer.

http://www.russia-direct.org/opinion/mongolia-uncontested-buffer-state

Although Mongolia would not act as a full buffer against China, it
certainly reduces much of the border space and, as Chinese migration
to eastern Russia is increasing, can reduce the uncertainty of illegal
border crossing by Chinese migrants. In this sense, the U.S. pivot,
and subsequent Ã¢Â€ÂœemploymentÃ¢Â€Â of Mongolia to contain China not only
would make sense to Moscow but be welcomed by the Kremlin Ã¢Â€Â“ if
Washington will do the work that will ultimately benefit Russia, why
should Russia complain? As long as there are active relations between
Moscow and Ulaanbaatar, there is no tangible loss for Russia, merely a
stronger border state that is increasing its security capacities and
border security, while continuing to counter the large Chinese
presence in the region.

White cannot ally with either blue or red. But blue and red are not allies either and it could plausibly serve their purposes to have a semiautonomous buffer between them. Its alliance with a distant power increases its utility as a buffer. This little pocket of white poses no threat and will not allow either red or blue to use its lands as a Launchpad for military action against the other.

Switzerland in the various Franco-German wars (including the World Wars) provides a similar example, I think. If Isolated is, or contains, a natural invasion corridor between Red and Blue, then neither one is likely to tolerate the other taking it. If Red tries to take it, they risk a two-front war with White and Blue. Blue is better positioned, but Blue seizing Isolated might be enough to forge a temporary White-Red alliance. — Aug 22 at 17:45
@Deolater among Switzerland (with mountains and some army) there were Netherlands and Belgium wich was quickly defeated. The Allies thought Belgium was a buffer but they were wrong. It worth to note than 1.Allies can't establish defence line since it's different country and 2. Small buffer area can't mantain really big army. In case of OP anclave wouldn't hold half of White's army and has no reinforcements so it's weak part in the Red border against Blue — Aug 23 at 21:07

ColonelPanic 1,06618 · Answer 2 · 2018-08-22 12:48:53Z

To begin, even with rivers linking the isolated state to the sea and a powerful navy, if your tech is medieval, this does almost no good. Land based fortifications in presumably Red state will prevent any type of supply using strictly rivers. Even a simple (defended) chain across the river was used for centuries to deny adverse ship traffic.

Given your presented geographical constraints and military equality between the four states, I would say that there are three likely scenarios.

First, and most likely for short periods of time, Peace will break out. No country is in a militarily advantageous position to do much of anything (except as Demigan pointed out, maybe Blue to invade Isolated, given some other constraints).

Secondly, there will be periods of incrementalism in taking strategic territory. No one country can commit enough of its military strength against another country without some sort of tactical (incremental) or strategic (likely requiring something catastrophic to occur like widespread famine in one country) advantage. Maybe this is a military tech advancement which allows for force multiplication whereas Blue can divide its forces in such a way to invade say Orange but still maintain enough strength to defend against Red.

The likely third component of this cycle will ultimately be some sort of military/political pacts or economic drivers. You mention it has been tried, but that is the situation at the beginning of your very dynamic scenario. Open warfare such as in the second point will drive necessity towards finding another advantage to even the odds, and this often times means asking for help. Even if these aren't fully blown alliances, non-agression pacts or mutual attack strategies where land is taken in geographically dispersed regions and kept by the attacking force, can quickly eliminate or nullify one of the nations.

The above cycle will likely continue to play out, especially as technology advances unequally or catastrophic conditions create advantages for a well-placed and well-led side to exploit, allows it to.

If holding on to the Isolated territory is enough a priority, you will likely need to make some sort of pact with at least one of Red or Blue. Or make it worth their while, say economically, to not invade and allow your forces to safely pass. Hope won't prove to be much of a strategy here.

If you produce something unique to your peninsula which is needed by Red in their fight/defense against Blue, well, now you may have at least a bargaining chip for your relationship.

Securiger 2,172138 · Answer 3 · 2018-08-23 13:04:47Z

A few options

It was not like that in the Middle Ages. Nationalism only arose in the late Middle Ages / early Renaissance. There were many instances of small, isolated states, and they had complex webs of loyalties. Isolated Territory might be a vassal of State, yet still have alliances and obligations to the marcher lords of Blue and Red and be co-religionists with Orange. Only when everything breaks down do they go to war -- and even then, it is rarely a war of annihilation or conquest. Often, the loser just has to offer a suitable pay-off.

Consider Afghanistan: fairly weak country, surrounded by more powerful states, which generally maintained independence for most of its history due to a combination of extremely difficult terrain and having no resources worth the effort.

Economics: Isolated Territory might have economic value to Blue, Orange and Red that is only applicable when it is a territory of State. For example, it might possess a rare herb or mineral that can only be processed into valuable goods by the skilled artisans of the capital of State. B, O and R constantly scheme to find the secret, but until they do, it is more profitable to trade with White than to invade its territories.

The economics argument can be simpler: it just requires the isolated territory to be a producer of something rare that red and blue want. As long as it remains independent of both it trades with both. But if one invaded it, the other must also, so it would end up red vs blue; but neither wants to risk a war with each other. — Aug 24 at 12:10

Mathaddict 70711 · Answer 4 · 2018-08-23 15:10:01Z

Fortify and Breed

Since we're in Medieval, terrain based fortification will be quite effective. While you've indicated that the smaller state could not survive a prolonged confrontation, the fact that the fortifications exist is a deterrent to confrontation. Especially when there are multiple countries of roughly equal strength. This is because the military advantage in the conflict between 4 warring states will go to the one who is the last to enter into battle, as they will have the numerical advantage after others have suffered losses.

Encourage your people to have as many children as your production can support. Over time this will give you the best chance of success in the conflicts.

Lie

Not directly, but it'd be best if you tried to make the other countries think that your country has a secret alliance with another one (this should be considered as extremely likely since any two working together should be able to defeat the other two working independently). If they feel like their being baited into attacking, they probably won't.

ADS 2,006311 · Answer 5 · 2018-08-24 10:18:33Z

If we discuss about war between countries over whole continent, it's more likely geo-politic strategy than pure war strategy. Let's look at the answers from Willk, ColonelPanic and Securiger (top at this moment). Both have paragraphs which related to geopolitics. Military maneuvers, army disposition, army structure and eventually war is only part of geopolitics. That's why my answer has little pure war options

Territory exchange

When I see in the long run I render it as several decades, probably century. It's extremely hard to control distant anclave not only during the war. Taxes, governor, communications are problems. Even language and culture will differ. So why White should hold anclave?

The exchange could be not only by a treaty. White could evacuate all forces from anclave and conquer another territory which easy to defend

Territory abandonment

Sovereignty doesn't fall when first city has fallen. If anclave is just another province, then it's good idea to significantly reduce border line and abandon the anclave.

If there is some unique resoucre and/or other ultimate need (say, the capital and governor is situated in anclave) then Red and Blue would have more reasons to conquer anclave. In extreme White could be considered as colonial country where big south part is colony which could be reduced/abandoned and most of the army is situated in 'anclave'.

Losses during anclave conquest vs Benefits from it

If anclave is a mountain region which easy to defend and it has no rare resources then both Red and Blue could select another targets which easier to attack. At the same time, Red need some guarantiees that Blue doesn't attack through anclave like Germany attacked France through Belgium. That guarantiees make sure Red forgo from preventive attack just to build up defence line.

Will Hartung 28113 · Answer 6 · 2018-08-22 16:25:55Z

The viable strategy is simply that if the eastern province is attacked, the western province attacks. Basically, the western forces act as a deterrent. You can't "stop" the attack in the east, but you, ideally, ensure that were it attacked, the price is higher than the gains.

Dan W 1,50539 · Answer 7 · 2018-08-24 11:32:28Z

Sorry, this isnÃ¢Â€Â™t really a complete answer, but may lead to one - others please feel free to flesh out the historical details.

For historical examples, the most relevant would be to consider West Berlin. This lasted for 28 years, including 3 years of blockade.
I suspect that key to the success of West Berlin was that the occupants strongly wanted to be identified with the West?

Also relevant is how the British empire and others sustained distant territories, though I think they would largely have had direct naval access?

Willk 85.6k21170372 · Accepted Answer · 2018-08-22 13:41:56Z