Timoleon was distinguished for gentleness as well as for courage, but towards traitors and despots his hatred was intense. He had once saved the life of his elder brother Timophanes in battle at the imminent peril of his own; but when Timophanes, availing himself of his situation as commander of the garrison in the Acrocorinthus, endeavoured to enslave his country, Timoleon did not hesitate to consent to his death. Twice before had Timoleon pleaded with his brother, beseeching him not to destroy the liberties of his country; but when Timophanes turned a deaf ear to those appeals, Timoleon connived at the action of his friends, who put him to death, whilst he himself, bathed in a flood of tears, stood a little way aloof. The great body of the citizens regarded the conduct of Timoleon with love and admiration. In the mind of Timoleon, however, their approving verdict was far more than outweighed by the reproaches and execrations of his mother. For many years nothing could prevail upon him to return to public life. He buried, himself in the country far from the haunts of men, till a chance voice in the Corinthian assembly nominated him as the leader of the expedition against Dionysius.
Roused by the nature of the cause, and the exhortations of his friends, Timoleon accepted the post thus offered to him. His success exceeded his hopes. As soon as he appeared before Syracuse, Dionysius, who appears to have abandoned all hope of ultimate success, surrendered the citadel into his hands, on condition of being allowed to depart in safety to Corinth (B.C. 343). Dionysius passed the remainder of his life at Corinth, where he is said to have displayed some remnants of his former luxury by the fastidious taste which he showed in the choice of his viands, unguents, dress, and furniture; whilst his literary inclinations manifested themselves in teaching the public singers and actors, and in opening a school for boys.