6 – Dionysius I: Syracuse (405 – 367 BC)
While many of the tyrants on this list were good rulers, Dionysius more than lived up to the version of ‘tyrant’ we’re aware of today. According to ancient historians, he was one of the cruelest and most vindictive rulers in the ancient world. Also known as Dionysius, the Elder, he was born sometime between 432 and 430 BC. He began his career as a clerk in a public office but soon made a name for himself in the war against Carthage in 409 BC. Dionysius was elected supreme military commander in 406 BC and used his position to seize power with the aid of Greek mercenaries.
It didn’t take him long to show his tyrannical tendencies. He faked an assassination attempt to receive increased protection. Dionysius initially had 600 bodyguards but increased the number to 1,000. He faced rebellions among those opposed to his illegitimate rule, but strangely enough, he enjoyed positive relations with Sparta. This is odd because the city state of Sparta was historically one of the most opposed to tyranny.
Dionysius subdued several Greek city states in eastern Sicily; then he started a war with Carthage for control of Sicily. After relying on Greek mercenaries for a few years, Dionysius embarked upon a complex program that involved creating weaponry, warships and siege engines in 399 BC. His investment paid off within a few years as he used his new war machine to defeat Carthage at Motya in 396 BC. The battle included the use of the first artillery machines in recorded history; catapults powered by mechanical tension.
However, the Carthaginians launched a successful counteroffensive. At one stage, they even managed to put Syracuse under siege. The Syracusans caught a lucky break when the Carthaginian army was decimated by plague. Dionysius defeated his enemy and negotiated an advantageous treaty in 392 BC. Syracuse defeated the Italiote League in 389 BC, and two years later, it captured Rhegium which gave it control of southern Italy; the tyrant sold the inhabitants as slaves. Dionysius renewed hostilities with Carthage in 383 BC but suffered a decisive defeat at Cronium in 378 BC and had to sign a peace treaty.
Overall, despite being a military innovator, Dionysius’ protracted wars ultimately weakened the Syracusan position in Sicily. He started yet another war with Carthage in 368 BC, but this time, he didn’t live to see the end of it. There are different versions of Dionysius’ death in 367 BC. According to one tale, he drank himself to death. However, others suggest that his son instructed physicians to poison the tyrant.