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Countries which are in a catch-22 situation
in Politics
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First, let us consider economically sanctioned countries, such as North Korea, Iran or Cuba. To prosper economically, they need sanctions to be removed. However, for the sanctions to be removed, they must conduct reforms that give people freedoms and rights - and the state cannot afford it under the current economical conditions, as the people would immediately take the opportunity, rebel and take the state down. Hence the state can never get out of the worldwide isolation without demolishing itself.
Then, "eternal conflicts", such as Israel - Muslim world, Russia - Eastern Europe, Ethiopia - Eritrea... Take Israel - Muslim world. Israel cannot make peace with the latter, since the Islamic countries would take it as a weakness and use it to gain more foothold, violating the peace. Similarly, Islamic countries cannot make peace with Israel, because Israel will take the opportunity and establish its dominance in the region on, and then proceed with the current unfriendly course. The peace is not possible, until one of the sides changes to something unrecognizable, that is perceived differently by the other side. Escaping the "eternal conflict" is impossible.
Next come projects two hostile sides are interested in, without being able to complete them due to mistrust. For example, mainland China and Taiwan had wanted to build a bridge connecting them for many decades now, which would dramatically reduce trade and travel costs. The biggest problem is caused by the simple question: who is going to control the bridge? Mutual control is impossible, since neither government recognizes the other as legitimate. Taiwan cannot let China control the bridge, because it fears it can be used for a military invasion - and China cannot let Taiwan control the bridge, because Chinese politics is very heavily regulated and Taiwan with its freedoms cannot be allowed to control a vital part of the Chinese land. Hence, the bridge can never be built, even though both sides would really love it to be built.
But the funniest (or the saddest, depending on how you look at it) two-sided catch-22 situation is probably Russia's and US' nuclear weapons. Each side wants to live in the world with no nuclear weapons. However, if Russia destroys its nuclear weapons, then the US will get a huge advantage by not destroying theirs. Hence Russia cannot destroy its nuclear weapons. But then, the world with no nuclear weapons becomes impossible. Same goes for the US.
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