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Plutarch treats the legendary meeting of Alexander the Great and Diogenes the Cynic in detail no fewer than three times. Given the popularity of this anecdote, starting already with Cicero (Tusc. 5.92), Plutarch’s interest in it is not surprising as such. What I investigate in this paper is how he presents the meeting in different contexts. Plutarch’s engagement with this larger-than- life moment ultimately constitutes, I argue, a reflection on the problems and potential of Cynic leadership.

In his Life of Alexander Plutarch describes how initially Alexander was surprised that Diogenes did not come to congratulate him in Corinth. When the two meet Diogenes, of course, asks Alexander to get out of his light. Unlike his companions, who make fun of the philosopher, Alexander ‘was affected and astonished’, saying that ‘if he were not Alexander, he would be Diogenes’ (Alex. 14). Plutarch also includes here Alexander’s choice of Diogenes’ student Onesicritus for chief-helmsman of his fleet (Alex. 65-66).

In To an uneducated ruler Plutarch describes how Alexander almost failed to live up to Diogenes’ call to philosophy, but in fact ‘became Diogenes and remained Alexander’, all the more so since he needed ‘heavy ballast and a great helmsman’ in his storm-tossed life (Mor. 782A-B). In On the fortune or the virtue of Alexander Plutarch argues that Alexander would follow in Diogenes’ footsteps if he had leisure; as it is he imitates Heracles, spreads Diogenes’ fame throughout the world, and, ‘just like Diogenes changes the currency, to stamp the foreign with Greek rule’ (Mor. 331E-332C).

Interpretations of Plutarch’s treatment of Alexander have focused on how the ruler, Alexander, adopts philosophy in order to become a better ruler (Roskam 2002; Boulet 2013; Klooster 2018). While this issue is clearly important to Plutarch, the reverse trajectory - how a philosopher, such as Diogenes, might be a leader - is of equal significance in his representations of the event.

The memorability of the meeting of Alexander and Diogenes seems to hinge on the incongruity between them: the grandeur and leadership of Alexander vs. the lowliness and hostility of Diogenes. Plutarch, however, consistently foregrounds the closeness between the two men (pace Van Raalte 2005). After their meeting Alexander admires Diogenes’ grandeur. Diogenes becomes Alexander’s helmsman, both literally, through Onesicritus as intermediary, and metaphorically on his ship of fortune (Mor. 782B). Alexander follows Diogenes’ example in changing the currency. Even his apologetic statement that he has to follow Heracles has a Cynic bent, since the club carrying hero was a well-known exemplar for Diogenes.

Diogenes’ leadership is starkly different from that of the eloquent, courageous, and well-trained men populating the Lives. Nonetheless, Plutarch recognizes the powerful effect that Diogenes’ provocative independence of spirit must have had on those who met him, put into sharp relief by how Alexander, model of leadership par excellence, comes under his sway. Plutarch anticipates later reflections within the Cynic tradition on the contradictions inherent to Diogenes’ charisma. In Diogenes Laërtius, for instance, Diogenes compares himself to chorus leaders who set the note a little too high so that others will hit the right note (D.L. 6.35).