Mark Antony
Caesar's best general and worst-remembered heir, who lost the Roman world to a sickly twenty-something and got written out of history by the winner.
Mark Antony spent his career being the obvious choice and losing to the unobvious one. He was the better soldier, the more popular figure with the legions, and for a decade the most powerful man alive. He ended by killing himself in Alexandria while his rival's fleet closed in, and because that rival went on to rule Rome for forty-four years, almost everything written about Antony afterward was written by people with an interest in his ruin.
He was a Roman aristocrat of undistinguished branch, spendthrift and physically imposing, who made his name as a cavalry commander under Julius Caesar in Gaul. As tribune in 49 BC he vetoed the Senate's move against Caesar and then fled Rome, which gave Caesar the pretext for crossing the Rubicon. At Pharsalus he commanded the left wing against Pompey. By 44 BC he was Caesar's fellow consul, and at the Lupercalia festival that February he publicly offered Caesar a diadem, which Caesar publicly refused, twice, in a piece of political theater nobody has ever satisfactorily explained.
After the Ides
The assassins spared him, which was their most expensive mistake. In the days after Caesar's murder Antony played a difficult hand superbly: he negotiated an amnesty with the conspirators, secured Caesar's papers and his personal fortune from the widow, and then delivered the funeral oration that turned the Roman crowd into a mob and drove the assassins out of Italy.
What he did not anticipate was the will. Caesar had adopted his teenage great-nephew Octavian as his heir, and this unimpressive eighteen-year-old arrived in Italy, claimed the name, and began buying the loyalty of Caesar's veterans with Caesar's money. Cicero, who despised Antony, delivered a series of savage speeches against him and backed Octavian on the theory that the boy could be used and discarded.
Antony and Octavian fought, then did the arithmetic and stopped. In late 43 BC, with Lepidus, they formed the Second Triumvirate, a legalized dictatorship of three, and financed it with proscriptions: published death lists, property confiscated, informers paid. Cicero's name was on the list at Antony's insistence, and his head and hands were nailed up in the Forum. In 42 BC the triumvirs destroyed Brutus and Cassius at Philippi, where Antony did nearly all the fighting and Octavian was reportedly ill in a marsh.
Cleopatra and Actium
The empire was divided: Octavian took the west, Antony the east and the war against Parthia that Caesar had planned. In 41 BC he summoned Cleopatra to Tarsus to answer for her conduct in the civil war and was comprehensively out-maneuvered by her. They became lovers and, eventually, political partners; Egypt had the grain and the money his eastern campaigns required.
His Parthian invasion in 36 BC was a disaster that cost tens of thousands of men. Meanwhile he had married Octavian's sister Octavia to seal the alliance, then abandoned her for Cleopatra, then in 34 BC staged the Donations of Alexandria, handing eastern territories to Cleopatra and to the children he had fathered with her.
Octavian, who was a mediocre general and a genius of political messaging, turned all of it into propaganda: Antony was a Roman gone native, bewitched by a foreign queen, planning to move the capital to Alexandria. In 32 BC he seized Antony's will from the Vestal Virgins and read it publicly, revealing that Antony wished to be buried in Egypt. Rome declared war on Cleopatra, carefully, so that it was not a civil war.
The fleets met off Actium on the western coast of Greece on September 2, 31 BC. Antony's force was blockaded, undersupplied, and losing men to desertion and disease; the battle ended with Cleopatra's squadron breaking out and Antony following. The following summer, with Octavian at the gates of Alexandria and a false report that Cleopatra was dead, Antony fell on his sword.
The loser's afterlife
Octavian became Augustus, and the version of Antony that survives, the drunkard, the dupe, the Roman unmanned by an eastern queen, is substantially his construction, repeated by Plutarch and then by Shakespeare. It is worth holding it at arm's length. Antony was a capable commander and a shrewd politician who held the Roman east for a decade.
He also lost, and the shape of his defeat mattered enormously. Rome ended up with one ruler rather than a permanently divided empire with a Greek-speaking half. That division would eventually happen anyway, three centuries later, which suggests Antony's instinct about where the wealth and population of the Roman world actually lay was better than his ability to hold it.