When Romans started encroaching on the territory of Greek colonies in Magna Grecia, a capable military commander was summoned to help them. This was Pyrrhus of Epirus, cousin of Alexander the Great. Although Pyrrhus would win several battles against the Roman, each of those victories would put him in a worse position.

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Sources:
Plutarch, "Parallel Lives"
Polybius, "The Histories"
Dio Cassius, "Roman History"
Anthony Everitt, “The Rise of Rome”
Mary Beard, "SPQR: A History of Ancient Rome"
Mike Duncan, "The History of Rome"

Special thanks to:
tjcold