Following the Second Italo-Ethiopian War in 1935, Kaleb's friends opted to stay at the newly conquered colonial capital Addis Ababa; Kaleb himself, however, continued his voyage to the southwestern newly Italian-designed city of Jimma in early 1939, employed under the monarchial house of the town’s king Aba Jifar's family.
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Since he was Eritrean and best friend to two of the top-ranking Eritrean-born Ethiopian Generals, General Aman Andom and General Bereket, Kaleb's case was weighed more than the any other Ethiopian, and he was accused of helping the ELF (Eritrean Liberation Front), and also alleged that he ordered the ruthless interrogations of one of his employees who stole from him more than 150,000,000 Ethiopian birr, which was found later to be a simple fabrication by the junta's cadres.