Pompey the Great: Rome’s Most Illustrious General, Part I

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Julius Caesar, Spartacus, Sulla, Marcus Crassus—these men have had a tremendous impact on the history of Rome. We’ve done biographies on all of them, and each time we mentioned another man who influenced their lives and careers: Pompey. He was arguably the most successful military leader that Rome had ever known, and today we’re giving him his due. It’s time for the man himself to take center stage in a special extended two-part biographic series as we look at the life and career of Pompey the Great.

Pompey was born Gnaeus Pompeius Magnus on September 29, 106 BC, in the region of Picenum. He was part of a family that was climbing the social ladder in Rome. Just a few decades earlier, the name Pompeius would have meant nothing to the average Roman; they were plebeians, meaning they were free Romans but not part of the elite patrician class—basically, just commoners. However, in 141 BC, a man named Quintus Pompeius became the first family member to receive a consulship, opening the door for other Pompeians to attain important political offices and fill the family coffers. By the time Pompey was born, his father, Gnaeus Pompeius Strabo, was among the richest men in Picenum.

That being said, it appears Strabo was not a popular man. Quite the opposite, in fact. Plutarch noted that when Strabo died, seemingly after being struck by a thunderbolt, people took his body from the funeral pyre and dragged it through the streets while throwing stones and hurling insults at it. So, he was not exactly a man of the people, which put him in stark contrast with Pompey. In fact, Plutarch mentions that never in Roman history had there been a bigger gulf between father and son in terms of how much the people hated one and loved the other. The historian fawns over Pompey, saying, “No Roman ever enjoyed heartier goodwill on the part of his countrymen or one which began sooner or reached a greater height in his prosperity or remained more constant in his adversity than Pompey did.”

There were many reasons for the love bestowed on Pompey: his modest and temperate way of living, his training in the arts of war, his persuasive speech, his trustworthy character, and his tact in meeting people so that no man asked a favor with less offense or bestowed one with a better grace. Suffice to say, Pompey was a popular figure among the people.

Now, we’ve probably mentioned this before, but it is worth repeating: barring extraordinary examples such as Pompey, the Romans had a pretty standard sequence for the men of the upper classes to advance their careers. It was called the cursus honorum, starting with the office of quaestor and ideally ending with the position of consul. Before that, it was expected that men would serve in the military, which meant that was Pompey’s first stop. He joined his father’s command around 90 BC and fought in the Social War. This was not one of Rome’s more famous conflicts, but it was important nonetheless because it led to the complete Romanization of Italy.

In 91 BC, the allies of Rome went to war, unhappy that they weren’t granted the same rights as citizens of Rome. The fighting went on for four years, and even though Rome won, the allies ultimately got what they wanted as they were granted Roman citizenship to avoid similar conflicts in the future. Strabo obtained his biggest moment of glory at the Battle of Asculum in 89 BC and was celebrated on the streets of Rome with a triumph, being named consul for that year. As far as Pompey was concerned, it was a bit too early for him to shine as a soldier. However, in 87 BC, once his father died and he inherited the family estate, that became a different matter entirely.

Pompey didn’t have to wait too long to put his burgeoning military prowess to good use because in 84 BC, Rome became embroiled in its fiercest power struggle yet, known as Sulla’s Civil War. If you want the full picture of that conflict, you can check out our previous video. Basically, Rome was in the grips of a civil war between two factions: one led by Sulla and the other by Gaius Marius and Lucius Cornelius Cinna. Early on in the war, it became evident that this wasn’t a conflict where other Romans could just stick their heads in the sand and wait for it to blow over; everyone had to choose a side or it would be chosen for them.

For Pompey, the decision was fairly easy since he bore a grudge against Cinna. Plutarch noted that the young Pompey escaped an assassination attempt engineered by Cinna while campaigning with his father. Given that Gaius Marius died early during the civil war and Sulla became the leader of his faction, it’s no surprise that Pompey decided to align himself with Sulla. However, he almost didn’t get the chance to do so, as he nearly lost everything at the outset of the war when the Marius-Cinna faction took over Rome. They began enacting proscriptions, declaring those found guilty as outlaws, confiscating their properties, and executing many just for good measure.

At first, they targeted supporters of Sulla, but they expanded their program to include many other Romans whose wealth they coveted. Pompey soon counted himself among those accused of stealing booty from the Battle of Asculum. If found guilty, his property would be confiscated, and he would be lucky to escape with his life. But instead, he managed to prove that a freedman in his father’s employ was the true thief, and his natural charm swayed the magistrates, who found him innocent. He even married the judge’s daughter, his first of five wives.

Realistically, Pompey probably escaped with his life and wealth intact because his enemies didn’t perceive the young and inexperienced soldier as much of a threat. Even so, Pompey knew not to tempt fate, so he quickly left Rome and retreated to Picenum. There, he seemingly fell off the grid for the next few years, but what Pompey was really doing was quietly recruiting troops and waiting for the right time to strike. That time came in 83 BC when Sulla and his army began marching on Rome. This was the point of no return for Pompey; once he aligned himself with Sulla, their fates were intertwined.

Both men ended up rich and powerful beyond their wildest dreams, or they both faced dire consequences. Another name you’ll probably recognize, Marcus Crassus, also allied himself with Sulla, as did another influential Roman general named Metellus Pius. Without a doubt, Pompey was the youngest and least experienced in that group, but he had two things going for him: first, he had the money to equip and train troops, and second, he was incredibly likable and charismatic.

You might think that this wouldn’t matter much in war, but the reality was that both sides were in full-on recruitment mode, and every man Pompey enticed to his side meant fewer soldiers fighting for his enemy. It is said that Pompey started out with only one legion when he left Picenum but had amassed three legions by the time he entered battle. Speaking of which, let’s get to that fighting.

By this point, Gaius Marius and Cinna had also died, and a man named Carbo was running the show. Before joining with Sulla, Pompey scored three quick and surprising victories against three of Carbo’s generals. When Carbo heard of this, he raced to meet this young upstart. When the two finally met, Pompey hailed Sulla as imperator. In return, Sulla got off his horse, took off his helmet, and returned the same greeting. This was a massive show of respect from the experienced veteran Sulla, who made it clear to everyone that the 23-year-old was now his protégé.

Pompey paid off this trust in spades. After meeting with Sulla, he left for Gaul, where he provided reinforcements. He wasn’t present at the decisive Battle of the Colline Gate, which won Sulla the civil war, but he was tasked by Sulla with chasing down the remaining opposition to prevent them from raising new armies and reigniting the conflict. This included Carbo himself, who abandoned Rome once he knew the war was lost. He intended to retreat to Africa to gather new troops but only made it as far as Sicily before Pompey caught up to him, captured him, and had him executed.

Pompey then crossed the Mediterranean into Africa and successfully crushed the last remnants of the Marius-Cinna faction at the Battle of Utica in 81 BC. Once his task was complete, it was time for Pompey to return to Rome and enjoy his spoils of war.

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Now, back to today’s video. The streets of Rome were flooded with cheers as Pompey made his triumphant return. Not to be outdone by the common rabble, Sulla greeted his protégé with the title “Pompeius Magnus,” or “Pompey the Great,” which he would use from then on. Sulla also arranged for Pompey to divorce his first wife and marry his stepdaughter, who tragically died during a miscarriage less than a year later. Along with respect and power, Pompey was granted untold wealth. Like Marius and Cinna before him, Sulla enacted proscriptions on his political enemies and allowed his closest allies to enrich themselves.

It didn’t take long for all this success to go to Pompey’s head. He was still in his mid-20s and already one of the richest and most powerful men in Rome. He felt like showing off. Nowadays, he might post pictures of himself in a private jet on social media, but Pompey wanted the first-century version of an Instagram brag: a triumph through the city streets. Sulla balked at the idea; nobody as young as Pompey had ever celebrated such an honor. According to Roman law, only a consul or praetor might receive a triumph, and Pompey, who had scarcely grown a beard, wasn’t old enough to even become a senator.

But Sulla had initiated a civil war and declared himself dictator, so who was he to lecture on Roman traditions? Despite protests from other officials, Sulla relented, and Pompey was granted his triumph. However, this little vanity project didn’t go exactly as planned. Instead of having his chariot pulled by horses through the streets, Pompey wanted it drawn by four elephants he brought back from Africa. Unfortunately, he didn’t realize that the elephants were too wide to fit through the city gates, so the procession had to stop outside of Rome and swap the elephants for horses while Pompey sat in his chariot, waving at everyone.

Despite occasional missteps, Pompey’s reputation flourished. If there was one thing that could endear someone to all classes of Rome, it was military glory, and Pompey had a spotless record. However, his meteoric rise rubbed some people the wrong way, including Sulla, who began resenting his young disciple. Tensions between the two increased over a man named Marcus Aemilius Lepidus, whom Sulla hated and called “the worst of men.” For whatever reason, Pompey liked Lepidus and publicly campaigned for him to be appointed consul.

The deterioration of the relationship between mentor and protégé became evident after Sulla’s death in 78 BC, as he completely snubbed Pompey in his will, even though he bequeathed gifts to his other friends. Furthermore, Sulla delivered a final “I told you so” from beyond the grave when Lepidus was named consul that same year and tried to stage his own rebellion to take over power by force. He was joined by Cinna the Younger, the son of the man who fought against Sulla, as well as Marcus Junius Brutus, the father of Caesar’s future assassin. Lepidus even asked a young Julius Caesar to join his uprising, but he wisely decided to stay out of it.

Lepidus’s main rival was a man named Catulus, the other consul. It’s worth reminding everyone that the Roman Republic always had two consuls at the same time to prevent any one man from gaining absolute power, although it certainly didn’t stop them from trying. Catulus wasn’t exactly praised for his military genius, so the Senate hoped Pompey might lend a hand. Unfortunately for him, despite his previous support of Lepidus, Pompey did a mea culpa and rallied against him. He was sent to Mutina in Gaul, which was Lepidus’s territory, to lay siege on Brutus, assuming Catulus would also be victorious.

Pompey’s siege was lengthy but successful, and upon capturing Brutus, he quickly had him executed, even though Brutus had surrendered. This wasn’t the first time Pompey had one of his opponents killed under questionable circumstances; Carbo had suffered the same fate, earning Pompey the nickname “Adlocutio Carnifex,” or “the teenage butcher.”

Meanwhile, Catulus also achieved his goal and defeated Lepidus at the Battle of the Milvian Bridge, although his victory wasn’t decisive enough to completely eliminate Lepidus as a threat. Once again, Pompey was sent in to obtain a more permanent result, which he achieved—sort of. He defeated Lepidus in battle, but Lepidus was still able to escape and flee to Sardinia, where he fell ill and died. So, mission accomplished.

Pompey had amassed an impressive military resume. Many commanders would have used all that glory to secure a safe position as a senator, governor, or even consul. In fact, that’s exactly what Catulus was hoping Pompey would do, given the last decade of conflicts right outside the city gates. Any military leader with command of a loyal army was cause for concern, after all. Who knows what ideas Pompey might get? That’s why Catulus told him to pay his soldiers, disband his army, and return to Rome to be properly celebrated for his victory.

As it turns out, Catulus was right to be concerned because Pompey did not want to disband his army. It seems that glory in battle tasted much sweeter to him than even the most sumptuous Roman banquet. But at the same time, he wasn’t so gung-ho that he was willing to make an enemy of the Senate, so he searched for a compromise by seeking out another conflict where his services might be needed. He found it in the Iberian Peninsula, or Hispania, as the Romans called it.

That region was under the control of a general named Quintus Sertorius, a former ally of Cinna and Marius. Sertorius had retreated to Hispania when his side lost the civil war, finding allies among local Iberian tribes and making himself the de facto ruler of the peninsula. Ever since then, Rome had been trying to retake control of the region but had failed to do so, as it didn’t allocate many resources to the problem since Lepidus was a more pressing issue. Sertorius proved adept at using guerilla warfare to disable his enemies and prevent pitched battles from happening.

This strategy worked for years. When Pompey got involved, Sertorius was already successfully foiling Pompey’s former military ally, Metellus Pius. Pompey’s actions were again questionable, as he disobeyed orders from Catulus and kept coming up with excuses to not disband his army. He relied on his supporters in the Senate, particularly a senator named Lucius Philippus, who realized they needed Pompey regardless of their feelings towards him. Philippus even suggested that Pompey be given the authority of a proconsul, referring to a military or administrative leader with powers outside of a regular term. Traditionally, only men who had previously served as consuls could be made proconsuls, but Pompey had never held the position of quaestor, the first stop on the cursus honorum. However, as we saw with his military triumph, Pompey was an extraordinary man for whom the standard rules simply did not apply.

Pompey arrived in Hispania in the spring of 76 BC, and this would be his home for the next five years, as Sertorius would prove to be his biggest challenge yet. Pompey started off his part in the Sertorian War with a rare defeat at the Siege of Lauron, not due to being outnumbered or facing a natural disaster, but simply because Sertorius was the better general. He allowed Pompey to think he had the upper hand when, in fact, he was falling for an ambush. The young, cocky Pompey realized too late that his men were marching into a trap, and he watched as up to 10,000 of his soldiers were slaughtered.

The shocking outcome left Pompey reeling. Some of the shine came off the golden boy who had seemed invincible until that point. However, he made a comeback the following year. Sertorius’s mistake was thinking that Pompey was a beaten man; he left him to his underlings while Sertorius went to deal with Metellus. But the Pompey of old returned at the Battle of Valentia in 75 BC, defeating Sertorius’s generals and inflicting massive losses on their armies, thus compensating for his earlier performance at Lauron.

The next time he fought Sertorius was at the Battle of Sucro and then the Battle of Saguntum that same year, both of which ended in stalemates. Afterwards, Sertorius decided to retreat into the mountains, regroup his forces, and resume his guerilla tactics by attacking supply lines and scouting parties. At the same time, Pompey’s side was starting to run thin on troops and resources, so he sent word to Rome asking