His relations with Antony did not go well. and when Julius Caesar's great-nephew and heir, Octavius, arrived and fell out with Antony over Caesar's will, Cicero supported him, outwardly at least. In private, Cicero said, "He should be given praises, honours, and the boot" and was most embarrassed when this got back to Octavian (as he was now called). Antony had to flee from Rome and was defeated by Hirtus and Pansa. Unfortunately both Hirtus and Pansa were killed in the battle, which left Rome without any consuls. Cicero delivered a series of ferocious speeches against Antony called the Philippics, after the speeches Demosthenes had given against Philip of Macedon.
Octavian and Antony were reconciled and formed the second triumvirate with Lepidus. The three of them drew up lists of political opponents who were to be put to death. Octavian fought hard to save Cicero but Antony, still smarting from Cicero's speeches against him, was adamant, and Octavian gave in. Cicero's name headed the list. Cicero and his brother Quintus were at Cicero's estate at Tusculum when the news of the proscriptions came, and they decided to flee to Brutus' army in Macedonia.
Quintus returned home for more supplies while Cicero continued on his journey. When he reached one of his villas on the coast, he dithered about whether to actually set sail or not until it was too late. On 7 December 43, while Cicero was being carried down to the sea in a litter, Herennius, one of Antony's centurions, arrived. Cicero ordered the litter bearers to put the litter down, and looking steadfastly at Herennius stretched out his neck. He was decapitated. His head and the hands, which had written his speeches against Antony, were taken back to Antony, who had them posted up on the rostra in the forum.
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