Pyrrhus(c.318-272 BC)

King of Epirus and cousin of Alexander the Great, known for his many battles. Married to Agathocles' daughter Lanassa.
When the Greek colony Tarentum asked Pyrrhus for help against the Romans, the king gladly accepted. According to legend, he asked the philosopher Cineas for advice. The philosopher asked the king what he would to after conquering Italy, and got the answer "Then I will take Carthage". Cineas asked what then, and got the reply "then we will take Macedonia, Egypt and Asia". "Then what", Cineas asked, "then we will celebrate and enjoy the pleasures of life", replied the king. The philosopher then said "why can't we do that immediately without challenging our destiny?"
At Hercalea Pyrrhus defeated the Romans with 25000men and 20 elephants in 280BC. The decisive factor for his victory was the elephants, an animal the Romans had never seen before. The horses ran away, terrified, and the Roman soldiers lost their courage. A year later Pyrrhus again defeated the Romans at the battle of Asculum.
The victories cost him so much, though, that the expression Pyrrhic victory has become an expression for a bitter victory. After this he went to help the Sicilian Greeks against the Carthaginians, now allies with the Romans, but became unpopular with them because of his despotic attitude.
In 275 BC he was defeated by the Romans at the battle of Beneventum, and returned to Greece with only one-third of his original force.
Pyrrhus was also involved with battles in Greece, and extended his kingdom into parts of Macedonia and Thessaly. Lysimachus, king of Thrace and consequently of Macedonia, later drove Pyrrhus out of his new lands. Pyrrhus again managed to conquer part of Macedonia in his defeating of the Macedonian king Antigonus II Gonatas in 276 BC. He was defeated by the Spartan army the year after, and fled to Argos where he was killed in a streetfight. His tactics and use of elephants was later to influence Hannibal.