The Horn of Africa’s short-lived Tripartite Alliance formed in 2018 by Eritrea, Ethiopia, and Somalia has collapsed, leaving behind a legacy of failed ambitions and political missteps. Initially framed as a partnership to strengthen political, economic, and security ties, the alliance was, in reality, a covert plan to wage war against Ethiopia’s Tigrayan People’s Liberation Front (TPLF). Ethiopian Prime Minister Abiy Ahmed, influenced by Eritrean President Isaias Afwerki’s centralist and anti-federalist vision, dismantled Ethiopia’s federal system, postponed elections, and cracked down on opposition. His miscalculations in Tigray have left Ethiopia in turmoil, with Tigrayan and Oromo forces advancing toward Addis Ababa. Somalia’s President Mohamed Abdullahi Farmaajo followed a similar path undermining federalism, manipulating state elections, and using force to seize territory from political rivals. Backed by Tripartite Alliance military cooperation, including troops trained in Eritrea, Farmaajo sought to consolidate power and even proposed extending his term. With Abiy on the brink and Isaias retreating into Eritrea, Farmaajo now stands isolated. The collapse of the alliance raises urgent questions: will he adapt and avoid the same fate, or persist in the same authoritarian trajectory, risking political disaster?