Sextus Pompey's Strategy

Sextus Pompey's Strategy

Came across a quote by Appian regarding Sextus Pompey "stricken with mental aberration, he never pursued an aggressive policy against his foes, although fortune offered him many opportunities; he only defended himself." It got me thinking about Pompey's strategy and what he could have done different. Could Pompey have won the war against Octavian had he been more aggressive? For a time he had Rome at his mercy by cutting its grain supply but decided instead to try the diplomatic route. Was this a mistake?
 
He only had a small part of the Empire, didn't he? And if he cut off the grain for Rome, they wouldn't love him even if he won.
 
IIRC he didn't really have any substantial legions, so even if he was able to completely cripple Octavian's half of the Empire with blockades/grain shortages, there's nothing he could do to follow it up and seal the deal. Even if Rome was starving, Octavian would prioritize keeping his legionaries paid
 
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He only had a small part of the Empire, didn't he? And if he cut off the grain for Rome, they wouldn't love him even if he won.

Sicily, Corsica and Sardinia. He would have to make sure the blame falls on Octavian not himself for the food shortages. That Octavian is refusing to make peace or something of that nature.

IIRC he didn't really have any substantial legions, so even if he was able to completely cripple Octavian's half of the Empire with blockades/grain shortages, there's nothing he could do to follow it up and seal the deal since. Even if Rome was starving, Octavian would prioritize keeping his legionaries paid

Good points. All I can think of at the moment is that Antony rolls the dice earlier and supporters him.
 
Honestly, if Pompey can form an alliance with Antony, then it all changes - as with Sicily he can then effectively just focus on attacking coastal cities and forcing them to submit.

If he'd taken a chance on Africa however, he could potentially oust Lepidus and have Sicily and Africa - and his own source of grain and manpower, independent of Antony.

But if he can take control over the supply of grain, and ensure every sack is marked with a message talking about how until Octavian surrenders and allows peace with the Senate, then all he does is bring suffering on the people of Rome - and effectively charging obscene prices, if Octavian doesn't want a riot on his hands then he's going to have to subsidise the price of grain (all of which has this message on it), which could bankrupt Octavian and bankroll Pompey, who can use the money to arm new Legions with massive sacks of grain being given away if the cities surrender without a fight. Complete clemency too. That could go a long way to undermine Octavian, and elevate Pompey.

You just need to paint a LOT of sacks of grain!
 
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