Timoleon had an older brother, whose name was Timophanes, who was every way unlike him, being indiscreet and rash and infected by the suggestions of some friends and foreign soldiers, whom he kept always about him, with a passion for absolute power. He seemed to have a certain force and vehemence in all military service, and even to delight in dangers, and thus he took much with the people, and was advanced to the highest charges as a vigorous and effective warrior; in the obtaining of which offices and promotions Timoleon much assisted him, helping to conceal or at least to extenuate his errors, embellishing by his praise whatever was commendable in him, and setting off his good qualities to the best advantage.

It happened once in the battle fought by the Corinthians against the forces of Argos and Cleonae, that Timoleon served among the infantry, when Timophanes, commanding their cavalry, was brought into extreme danger; for his horse being wounded fell forward, and threw him headlong amidst the enemies, while part of his companions dispersed at once in a panic, and the small number that remained, bearing up against a great multitude, had much ado to maintain any resistance. As soon, therefore, as Timoleon was aware of the accident, he ran hastily to his brother's rescue, and covering the fallen Timophanes with his buckler, after having received an abundance of darts and several strokes by the sword upon his body and his armor, he at length with much difficulty obliged the enemies to retire, and brought off his brother alive and safe. But when the Corinthians, for fear of losing their city a second time, as they had once before, by admitting their allies, made a decree to maintain four hundred mercenaries for its security, and gave Timophanes the command over them, he, abandoning all regard for honor and equity, at once proceeded to put into execution his plans for making himself absolute, and bringing the place under his own power; and having cut off many principal citizens, uncondemned and without trial, who were most likely to hinder his design, he declared himself tyrant of Corinth; a procedure that infinitely afflicted Timoleon, to whom the wickedness of such a brother appeared to be his own reproach and calamity. He undertook to persuade him by reasoning to desist from that wild and unhappy ambition, and bethink himself how he could make the Corinthians some amends, and find out an expedient to remedy the evils he had done them. When his single admonition was rejected and contemned by him, he made a second attempt, taking with him Aeschylus his kinsman, brother to the wife of Timophanes, and a certain diviner, that was his friend, whom Theopompus in his history calls Satyrus. This company coming to his brother, all three of them surrounded and earnestly importuned him upon the same subject, that now at length he would listen to reason and be of another mind. But when Timophanes began first to laugh at the men's simplicity, and presently broke out into rage and indignation against them, Timoleon stepped aside from him and stood weeping with his face covered, while the other two, drawing out their swords, despatched him in a moment.

When the rumor of this act was spread about, the better and more generous of the Corinthians highly applauded Timoleon for the hatred of wrong and the greatness of soul that had made him, though of a gentle disposition and full of love and kindness for his family, think the obligations to his country stronger than the ties of consanguinity, and prefer that which is good and just before gain and interest and his own particular advantage. For the same brother, who with so much bravery had been saved by him when he fought valiantly in the cause of Corinth, he had now as nobly sacrificed for enslaving her afterward by a base and treacherous usurpation. But when he came to understand how heavily his mother took it, and that she likewise uttered the saddest complaints and most terrible imprecations against him, he went to satisfy and comfort her, but he found that she would not endure so much as to look upon him, but caused her doors to be shut that he might have no admission into her presence, and with grief at this he grew so disordered in mind and disconsolate, that he determined to put an end to his perplexity with his life, by abstaining from all manner of sustenance. But through the care and diligence of his friends, who were very persistent with him, and added force to their entreaties, he promised at last that he would endure living, provided it might be in solitude, and remote from company; so that, quitting all civil transactions and commerce with the world, for a long while after his first retirement he never came into Corinth, but wandered up and down the fields, full of anxious and tormenting thoughts, and for almost twenty years did not offer to concern himself in any honorable or public action.