alternatehistory.com

In 1977 Fidel Castro arranged a meeting between Mengistu Haile Mariam of Ethiopia, Mohamed Siad Barre of Somalia, and Salem Rubayi Ali of South Yemen. During this time the Somali Democratic Republic was condemning Ethiopia over its treatment of the Somali majority in the Ogaden region of the country, and war would erupt months later between the two states in which the Soviets and Cubans would side with the Ethiopians.

Before this, however, Castro proposed an ambitious federation in which Ethiopia, Somalia and South Yemen (which had Yemeni populations in both Ethiopia and Somalia) would federate along with an autonomous Eritrea and autonomous Ogaden region (possibly a part of Somalia within the federation). Castro also hoped that the federation would encompass a socialist Djibouti one day. The Soviets expressed considerable interest in the plan and sought to make it work and Ethiopia was willing to go along with it (the South Yemenis didn't seem too interested) but Barre condemned it and called Mengistu a "fascist," and the two countries went to war soon after resulting in the proposed federation never occurring.

What if Barre (or someone else in his shoes) dropped his opposition to the plan and both Somalia and Ethiopia federated, with possibly South Yemen joining or having an associated relationship? 1970's and 80's Ethiopia was beset by various tribal rebellions IRL, and of course clan warfare (fanned by the Ethiopians IRL) in Somalia turned that country towards chaos in 1991, so the tasks of trying to unite all of these distinct ethnic and tribal groups (which were already unruly) would be quite a task.
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