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Decisive Battles of History: Philippi

Andrew is an avid reader of history who enjoys researching and discussing ancient Roman topics with others.

Political Background

After the defeat of Carthage during the Second Punic War, the Roman Republic became the hegemon of the Western Mediterranean World. Using the power and wealth they acquired by conquering Carthaginian domains in Spain, Sicily and later Africa, the Roman Republic turned its attention to the East during the second century BC. They went on to overrun most of Greece and set a permanent base in Anatolia too.

However, the expansion of the Republic did not lead to an equal share of the wealth that the Romans looted from their provinces. Quite the contrary, the inequality in the Roman society exploded during the expansion of the Republic and led to the widespread use of slave labour and the birth of a super-rich elite that, by the 1st century BC, became rich enough to privatize the institutions of the Republic.

As the Romans ran out of foreign enemies to fight, the rich elites of the Republic turned on each other. From the murder of the Gracchi brothers, Roman politics became increasingly more violent, and during the disputes of Gaius Marius and Lucius Cornelius Sulla, outright Civil War broke out between the two factions. The civil war lasted for years, and the two sides’ fortunes fluctuated, but in the end, Sulla and his supporters came out on top, and Sulla became the de facto dictator of Rome for a time.

However, Sulla had no intention of ending the Republic, and after he pushed through his pro aristocratic legislations, he willingly gave up on power and retired from public life.

Following Sulla’s retirement and death, several figures dominated Roman politics, but the two most important of them were Crassus and Pompey. They both supported Sulla during the civil war and made a name and a fortune in doing so. Crassus was regarded by many as the richest man in Rome, while Pompey was the greatest soldier of Rome who defeated a rebel general in Spain, ended the threat of the Cilician pirates and conquered much of the East during the 60s BC.

Unfortunately, the two-man detested one another. Crassus believed that Pompey stole his glory of defeating Spartacus, and he was probably partially in the right here. He used his influence to screw Pompey at every opportunity he got in the next decade.

The Rise and Fall of Caesar

The rivalry between Pompey and Crassus came to an end when Gaius Julius Caesar succeeded in bringing them together. In exchange for supporting his bid to become consul, Caesar promised to push through legislation that would benefit both Pompey and Crassus.

The mutual interest allowed the birth of the First Triumvirate, which dominated Roman politics throughout the 50s BC. However, it came to an end when Crassus was killed in his botched invasion of the Parthian Empire.

After the death of Crassus, Caesar and Pompey drifted apart, and the two of them soon became enemies. Pompey allied with the aristocratic faction, the Optimates, while after his successful conquest of Gaul, Caesar became the new champion of the people, the Populares faction.

Caesar’s political enemies watched his rapid conquest of Gaul with many worries and tried to outmanoeuvre Caesar in the Senate. When all political means to defend himself were exhausted, Caesar decided to start a civil war rather than give up command over his armies and return to Rome to face his enemies alone.

Ceasar’s Civil War lasted for four years, but in the end, Caesar overcame all his enemies and, after the Battle of Munda, became the sole master of the Republic.

Unlike Sulla, Caesar did not kill his enemies but chose to spare them. This generosity came to be his undoing, as his former enemies formed a conspiracy and murdered Caesar in the Senate in 44 BC.

The killers of Caesar claimed that they were saving the Republic from a tyrant, which may even be the truth, but the Roman mob who adored Caesar had little interest in such fancy political theories. Caesar’s right-hand man Mark Antony incited the mobs against the Liberators (what the killers of Caesar called themselves), and they had no option but to flee from Rome to save their lives.

The Aftermath of Caesar’s Death

Once he got rid of Marcus Brutus and Gaius Cassius (the leaders of the Liberators), Antony probably believed Rome was his for the taking; however, he was in for a shock. His old enemy Cicero made his life hard, and a new, unexpected player arrived on the scene too.

In his will, Caesar named his great-nephew Gaius Octavian as his heir, and the young Octavian, once he arrived back in Rome, became the enemy of Antony. Antony soon became a public enemy and was forced out of Rome. After his defeat at Mutina, he layed low in Northern Italy.

On the other hand, Octavian used his newfound influence to force the Senate to condemn the murder of his adoptive father, Caesar. Cassius, Brutus and his fellow conspirators thus became public enemies.

Cassius and Brutus were not sitting on their laurels either. They succeeded in subduing the eastern provinces of the empire with the intention to use this wealth and manpower to retake Rome for themselves. Brutus and Cassius collected in total 17 legions and several thousand auxiliary troops. This army, even if the legions were probably understrength, was larger than anything Octavian or Antony could throw at them on their own.

Facing imminent danger, Antony, Octavian and Marcus Lepidus (who was an ally of Antony) formed an alliance that became known as the Second Triumvirate. Now united, the three of them had a slight numerical advantage over their enemies. They decided to purge their enemies in Rome, and a massacre of their rivals followed. They confiscated the wealth of their killed enemies and used the money to shore up the support of their troops.

Lepidus remained behind in Italy to keep an eye on the Senate, while Octavian and Antony crossed into Greece to confront Cassius and Brutus. Octavian and Antony sent ahead their lieutenants to block the advance of their enemies, but Cassius and Brutus outmanoeuvred them.

The Liberators arrived at a small town named Philippi and set up their camps there. They had selected the place wisely as forests and marshes defended their flanks, and they made their camps on two hills. To protect themselves from a frontal assault, the liberators built walls and palisades from the forests to the marshes; that way, they were well prepared for attacks from all directions.

Antony led the army of the Triumvirs against them, but by the time he arrived, he found the Liberators in a well-entrenched position. He began to build his own defences, and once the ill Octavian arrived at the scene, the army of the Triumvirs took a similar shape to that of the Liberators, as Antony and Octavian took command over one camp each.

The Battle of Philippi

The Liberators were happy enough to stay on the defensive and wage a war of attrition. They had good reason for this, of course, as their supply lines coming from the east were secured, while the supply lines of the Triumvirs were harassed by the navy of the Liberators and their allies.

Antony and Octavian understood their situation perfectly and tried to goad their enemies into attacking them, but Cassius and Brutus turned a deaf ear to their provocations. Seeing that their enemies would not be provoked into battle, Antony decided to build a path through the marshes, using which he could outflank the Liberators.

Cassius responded by lengthening his own defences; however, to this end, he had to divert men from his initial defences. Antony attacked the weakened sections of the walls, and his men overwhelmed the defenders and broke into the camp of Cassius.

In response to Antony’s attack, the man of Brutus staged their own attack against Octavian’s camp and completely overwhelmed their enemies. The men of Brutus stormed the camp of Octavian, but luckily for Octavian, he was able to escape and, for a time, hid in the marshes.

The commanders poorly coordinated the battle, and for a time, they probably had a hard time understanding what was really going on.

This was demonstrated perfectly by Cassius, who Antony defeated. Cassius retreated from his camp, and when the cavalry of Brutus approached him to bring the news of Brutus’s victory, he mistook them for the Triumvir cavalry and ordered his men to kill him before he was captured.

The first phase of the Battle of Philippi ended in a stalemate, as each side scored one victory and suffered a defeat, but both sides had more than enough men to continue the fighting. Crucially though, the Liberators lost Cassius, a much more experienced military leader than Brutus, who struggled to impose his will on the army in the aftermath of Cassius’s death.

Both sides regrouped in the aftermath of the first battle; however, Brutus crucially decided to shorten his defences and abandoned part of the wall. Antony used this to penetrate the defence of Brutus and tried to outflank his rival by building a parallel wall to the marshes.

He no doubt hoped to cut Brutus's supply lines, but in response to Antony’s move, Brutus built his own walls. The soldiers of Brutus seemingly lost trust in their commander as the weeks passed and forced him into giving battle three weeks after the first one.

According to historians, no great strategic manoeuvres took place during the battle, and it was a real infantry versus infantry slogging brawl. In the end, it was the army of Brutus that broke first and thus lost the battle. Brutus fled from the battle but, believing his capture was inevitable, ordered one of his friends to kill him.

The Fall of the Republic

As the battle was lost and their commanders were gone, the surviving army of the Liberators surrendered in its entirety. The legions were divided between Antony and Octavian.

With the defeat of Cassius and Brutus, the Republican cause was much weakened. In the following years, slowly but surely, the Triumvirs defeated the rest of their enemies in Sicily and in the East. Brutus and Cassius wanted to save the Republic from falling into tyranny, but their defeat led to the exact conclusion they wanted to avoid.


Arthur, Colin. (2005). The Fall of the Roman Republic. Routledge.

Holland, Tom. (2005). Rubicon: The Last Years of the Roman Republic. Anchor.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2022 Andrew Szekler