WI: Sextus Pompey defeats Octavian in Sicily

Whenever I see Roman TL's based around the time of Caesar and the wars of the second triumvirate, i see that a certain larger then life character is sadly missing-Sextus Pompeius Magnus Pius, the youngest son of Pompey of the great, who, having seen his father murdered in Egypt, devoted his entire life fighting both Caesar and his successors.
http://en.wikipedia.org/wiki/Sextus_Pompey

He fought with his older brother Gnaus first at Munda in Spain, only to be defeated and began a successful guerrilla commander in Spain. Following Caesars death he went to Sicily where he lead a pirate fleet against Marcus Antonius' forces. It is here that things took a turn for the better, when he was given control of several Roman fleets and began to take control of Sicily . With both these at his control, he began to both build up his forces while blockading both Marcus Antonius and Octavian in Italy. Cut of from food, the angry roman populace rioted against both generals, forcing them to use proscriptions ( copied from the dictator Sulla) to get money for their campaign against the Liberators Cassius and Brutus. This drove many republicans and other key figures to flee to Sextus, who was viewed ( following the battle of Philipi) as the last hope of the republic.
He also became extremely popular with the lower classes.

Desperate to crush him, both Anthony and Octavian launched an expedition to crush Sextus, only to suffer numerous defeats at the hands of his fleet, including the loss of Sardinia to a fleet commanded by Sextus' commander Menas in 40BC. It was this that forced the Triumvirs to negotiate at Misunem, at which Sextus was given the Peloponnese, Sicily and Sardinia.
It was to prove to be a huge mistake, since under the treaty many republican exiles were forgiven, causing many of them to leave Sextus army. Worse, it shattered the confidence of one of his chief admiral, Menas, who had wanted to assassinate the two triumvirs at Miseum who deserted to Octavian along with two legions and Sardinia.

It soon appeared that Octavian had no intention of fulfilling his part of the agreement. In 37BC Octavian attacked again with a huge fleet, only to be defeated by Sextus, who despite having only 300 ships was able to use his superior seamanship to outmaneuver and destroy part of Octavian s fleet. Octavian raised a new navy, which led by his talented commander Agrippina defeated Sextus of Mylae in 36BC.

It is here that the what ifs accumulate. At Thurii, where Octavian was uploading is army, Sextus was able to surprise and surround Octavian's force, which was unable to get into formation. Here, Sextus had an opportunity to crush the Triumvirate fleet and capture Octavian, only to instead stand back and do nothing. The next day, Sextus again had an opportunity to crush Octavian, when, having got the better of the navel engagement, was able to cut of Octavian's ship. Fearing he was close to capture, Octavian ordered one of his officers to be ready to kill him, only to escape to Thurii, where he was again nearly killed by Sextus' horsemen, Republican legionaries mistaken for his own troops and even an assassination attempt by his freedman until he was finally rescued.

What if Octavian had been captured however? What if Sextus hadn't held back his forces the previous day, or the assassination attempt succeed? We already know that Sextus was in secret negations with both Antony and Lepidus, and was also popular with the senate and the lower classes. Could he have come to an agreement, with him ruling the western empire? Would civil break out again? Who would win? Could Sextus have restored the republic ( unlikely) or become an alternate " first among st equals-an emperor in all but name?
 

Anaxagoras

Banned
I love PODs like this. The 1st Century BC was such an unsettled time that any number of different things could have happened. If Sextus Pompey had defeated Octavian (and probably killed him), then you'd eventually have a showdown between Sextus and Antony, with Lepidus waiting to see who would emerge the victor.
 
Sextus Pompey was potentially a very powerfull figure.
So killing Augustus he might become a triumvire.
But what next?
I do not know. One possibility is division of the Roman state into three or two parts. Or the final confrontation to unite the Empire. And Sextus is possible winner and an able substitute for Octavianus Augustus as the founder of the Principate as a system.
 
Hmmm. There certainly will be a showdown between Pompey and Antony. Pompey seems to be an expert naval commander as well, so maybe we see another Battle of Actium (except obviously not the battle of Actium) doing it in for Antony?

Assuming he wins the civil war with Antony (and lets say Lepidus takes his side), I can see him doing something similar to what Augustus did-I mean his republican sympathies seem to make him an even likelier candidate to do just that than Octavian himself! In that case, I can see Menas (or even Lepidus?) be his immediate successor.
 
Hmmm. There certainly will be a showdown between Pompey and Antony. Pompey seems to be an expert naval commander as well, so maybe we see another Battle of Actium (except obviously not the battle of Actium) doing it in for Antony?

Assuming he wins the civil war with Antony (and lets say Lepidus takes his side), I can see him doing something similar to what Augustus did-I mean his republican sympathies seem to make him an even likelier candidate to do just that than Octavian himself! In that case, I can see Menas (or even Lepidus?) be his immediate successor.

Lepidus? I for one doubt it. From what the ancient sources state he was an unpopular and uncharacteristic figure. I think Octavians death may cause many of his men to defect to Sextus-afterall, Lepidus is going to be left out no matter who wins the conflict.
 
Lepidus? I for one doubt it. From what the ancient sources state he was an unpopular and uncharacteristic figure. I think Octavians death may cause many of his men to defect to Sextus-afterall, Lepidus is going to be left out no matter who wins the conflict.

True. So maybe Menas becomes his immediate successor?
 
True. So maybe Menas becomes his immediate successor?

Or maybe Sextus executes/assassinates him for backstabbing him? Or rather, Sextus is too "noble" and "honest" to do so ( the missed opportunity at Miseum shows this) so one of him more ruthless subordinates does so.

On another note-Agrippa. What will happen to him? He wasn't present at Thurii, and had already proved himself a capable navel commander at Mylae.
 
Or maybe Sextus executes/assassinates him for backstabbing him? Or rather, Sextus is too "noble" and "honest" to do so ( the missed opportunity at Miseum shows this) so one of him more ruthless subordinates does so.

On another note-Agrippina. What will happen to him? He wasn't present at Thurii, and had already proved himself a capable navel commander at Mylae.
*Agrippa. Agrippina would be the female form.
 
oops! just realised that! Thanks.
Anyway-what would happen to him?

I guess it depends on what his next move is and what Pompey does. I could see Pompey pardoning and or offering an alliance with him to show his clemency if Agrippa is willing to negotiate.

But at the same time...Agrippa himself is a top notch commander and if he gets the troops, could pose a real challenge to Pompey if he chooses to go against him. Maybe Agrippa makes some temporary alliance with Antony? Now that would prove a real test for Pompey...
 
Also, I can't seem to find anything on that last part about Octavian and Thurii. Do you have any links to it? I really want to look into it more because it seems interesting.
 
Also, I can't seem to find anything on that last part about Octavian and Thurii. Do you have any links to it? I really want to look into it more because it seems interesting.

I got this all from the excellent book by Anthony Everitt called "Augustus: the life off the first emperor."

Here is the orgignal source for this battle from Appian: The civil wars:
http://penelope.uchicago.edu/Thayer/E/Roman/Texts/Appian/Civil_Wars/5*.html#104

Alternatively, try typing in "battle near Taormina" August 36BC.

For some reason, very little is known of this extraordinary engagement that held the entire western world in the balance.
Sorry i couldn't help more!
 
Considering I'm actually performing in Antony and Cleopatra, I love this thread. :D

Worse, it shattered the confidence of one of his chief admiral, Menas, who had wanted to assassinate the two triumvirs at Miseum who deserted to Octavian along with two legions and Sardinia.
In-play, all three triumvirs are present at the conference at Miseum, which makes Menas' offer a lot more appealing. If all three had been assassinated, it would give Pompey sole ownership of Rome, and therefore the world.

What if Pompey became the third triumvir? Either Caesar or Antony would have liked him as a partner, assuming Pompey can be persuaded to kill the other.
 
Considering I'm actually performing in Antony and Cleopatra, I love this thread. :D


In-play, all three triumvirs are present at the conference at Miseum, which makes Menas' offer a lot more appealing. If all three had been assassinated, it would give Pompey sole ownership of Rome, and therefore the world.

What if Pompey became the third triumvir? Either Caesar or Antony would have liked him as a partner, assuming Pompey can be persuaded to kill the other.

No. Never. Lepidus was just there to to make up space and act as a buffer to both their ambitions-though in truth they knew he was so weak that he had no choice but to follow him. There were really just two triumvers at Miseum-and a poor Lepidus.
Octavian HATED Sextus with a passion. Antony by contrast was sympathetic and in contact with Sextus even during Octavian's campaign against him. So not a 3rd Triumvir-but maybe Antoneys partner in the west.
 
So I was thinking...If Octavian is killed on Thurii and in consequence Agrippa pulls back, what then?

I can see Lepidus's men deserting and maybe even killing him. With Lepidus and Octavian dead, Antony is the sole triumvir. But as you said, he had been in contact with Sextus. So what I was thinking, maybe the three make a Third Triumvirate? Antony being the head triumvir, and Sextus and Agrippa being the other two?

Alternatively, could Sextus and Antony team up and take out Agrippa? Maybe Sextus becomes the right hand man of Antony? Or will the two clash eventually?
 
So I was thinking...If Octavian is killed on Thurii and in consequence Agrippa pulls back, what then?

I can see Lepidus's men deserting and maybe even killing him. With Lepidus and Octavian dead, Antony is the sole triumvir. But as you said, he had been in contact with Sextus. So what I was thinking, maybe the three make a Third Triumvirate? Antony being the head triumvir, and Sextus and Agrippa being the other two?

Alternatively, could Sextus and Antony team up and take out Agrippa? Maybe Sextus becomes the right hand man of Antony? Or will the two clash eventually?

This scenario is possible-Antony would benefit from such an alliance as it frees him up for his Parthian campaign and eliminates his former troublesome colleague with a more cooperative one who could act as a source of reinforcements.
My guess is that Agrippina is sidelined pretty quickly as his fleet could act as what Sextus' fleet previously was: a powerful fleet capable of mass piracy and blockades. The two men would likely combine forces to crush Agrippa-due to his loyalty to Octavian, i find doubtful he would negotiate with the victors.
Of course, both Sextus and Antony respected him-its possible he could remain an officer in their armies.
 
This scenario is possible-Antony would benefit from such an alliance as it frees him up for his Parthian campaign and eliminates his former troublesome colleague with a more cooperative one who could act as a source of reinforcements.
My guess is that Agrippina is sidelined pretty quickly as his fleet could act as what Sextus' fleet previously was: a powerful fleet capable of mass piracy and blockades. The two men would likely combine forces to crush Agrippa-due to his loyalty to Octavian, i find doubtful he would negotiate with the victors.
Of course, both Sextus and Antony respected him-its possible he could remain an officer in their armies.

So not a triumvir, but an allied general in a way?
 
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