Politicians > Military Leaders > Businessmen, Really?



Between Gibbon’s Decline and Fall of the Roman Empire, Han Fei-tzu and my rapidly worsening podcast addiction, I’ve been learning an awful lot about ancient history recently. One of the themes I’ve kept running across is this pattern where good politicians seem to be much more important and much more powerful than generals or warlords. Generals and warlords, in turn, seem to have very little problem running over businessmen. Let’s go through some examples.


Julius Caesar, the man who out fought Pompey and out talked Cicero.

The First Triumvirate of Rome:

The first triumvirate consisted of Gaius Julius Caesar, who rose to prominence as a populist, left-wing politician, Marcus Licinius Crassus, who rose to prominence by being one of the wealthiest individuals in history, and Pompey the Great, who rose to prominence by kicking the living snot out of the Marians, the slaves under Spartacus and the tribes of Gaul.

Businessman Crassus, easily outmaneuvered by Pompey, died in a failed invasion of Parthia undertaken mostly because he was desperately trying to get somebody, anybody, to like him. General Pompey, outmaneuvered by politician Caesar, fell next. This is perhaps a little too neat, since Pompey was a good, but nowhere near Caesar-level politician and Crassus was a decent, but nowhere near Pompey-level general, but I think it’s instructional. Nobody liked Crassus and it showed. People did like Pompey, but not as much as they liked Caesar, and that showed as well.


Battle of Actium, Agrippa leading Octavian’s men against Mark Antony.

The Second Triumvirate of Rome:

The second version consisted of consumate politician Octavian, consumate general Mark Antony and Marcus Aemilius Lepidus, who was also a general but we’re mostly going to ignore him because he was a bit of a third wheel.

What’s really interesting about Octavian and Antony is that they were such extreme examples of their type. Octavian was a bad, bad, not good military leader but everyone agrees the man was a master administrator and savvy politician. Antony was a political disaster whose debauched lifestyle alienated the people of Italy and whose fling with Cleopatra, identification with Egyptian culture and elevation of eastern values thoroughly offended everybody else. However, everyone agrees Mark Antony was a brilliant military commander beloved by his troops.

Octavian won. He won despite starting off with the least resources. He won despite being 19 when the whole thing started. He won despite being an absolute turd of a military commander. The thing that amazes me about Octavian is how easily he secured the loyalty of really, really excellent military men to fight for him. Agrippa never seemed to consider turning on Octavian. Neither did the men serving under Agrippa. It seems that a good politician can find a good general when he’s in charge. A bad politician, on the other hand, can’t find a good person to be in charge while still being in charge himself.

Washington Princeton.jpg

George Washington, getting his butt kicked all the way to victory.

The American Revolution:

The American side of the Revolution had a number of historically gifted politicians like Thomas Jefferson, Benjamin Franklin and most especially politician George Washington. Unfortunately, General George Washington started the war off as a disaster of a military commander and really only worked his way up to average by the end.

The British politicians of the Revolution included an incredibly out of touch parliament, King George III and Governor Thomas Gage, who tied to passify the colonials through the unique strategy of pissing them off immensely. Fortunately, they also had Charles Cornwallis and his collegues, who tended to wipe the ground with George Washington’s troops whenever they tangled.

Again, the deft politicians and bad generals of the American side developed deep and stable ties to the population that provided them enough fresh men, supplies and moral to make up for the continuous losses in the field. Franklin also managed to get the French on board without compromising the American position post-war. The British, despite winning something like 90% of the battles, lost the war because their political bosses couldn’t stop irritating the locals, couldn’t keep France out of the war, and couldn’t keep their own people cooperating with each other.


Toussaint Louverture, getting ready to punk his rivals.

The Haitian Revolution:

This was basically a three way battle. There were the “big white” businessmen, who owned most of the island’s plantations and controlled Haiti’s access to France. They faced off against Toussaint Louverture, who I’d consider one of the most politically gifted men ever, and the successions of military men who washed in and out with every tide.

Louverture’s success in the revolution stemmed from his ability to alternately play and coopt the big whites, play and coopt the various military factions and most especially, his preternatural ability to read and manipulate the French. He quickly and efficiently dispatched the militant slave leaders, deftly undermined French control of the island and beat up on the rival claimants for power so badly that I almost felt bad for them. No Louverture, no way in hell Haiti works its way free of the slave system that had so long defined it.

When the French did eventually kill Louverture, it was the desperate and nihilistic act of a sore loser. Louverture’s death also put the final nail in the big whites’ collective coffin, resulted in a genocide for French citizens on the island and screwed Haiti for at least a century.

So, am I full of it? Would we be better off with great businessmen and weak politicians? Am I cherry picking rare instances of good generalship failing to bring victory? I’d love your thoughts.






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  1. I think you’re on to something, although I think it may be slightly more complicated.

    Power seems to be about understanding people, what motivates them, what alienates them, what makes them an ally or an enemy. It’s possible to luck out and get power without that understanding, but holding onto it can be a different matter, and the person who understands people better will usually win in a power struggle.

    Many people without that deep understanding of humanity can get to power by riding the coattails of someone who does understand it. But when the initial benefactor goes away, they usually struggle (at least unless they learned at some point).

    I think the most successful businessmen and generals benefit from that understanding, although it may be more possible in those areas to make up for shortcomings with specific technical competencies. In politics, understanding people is the core competency. You rarely find successful politicians who don’t have to it one degree or another, and master politicians typically have it in spades.

    1. Hey Mike,

      Thanks for the comment. I agree that people skills really seem to be what separates Caesar from Crassus, for example, or Washington from Cornwallis.

      What seems interesting to me, though, is that it seems that the type of people skills necessary to be a businessman are different from the type of people skills needed to be a military leader. Both of which are different from the people skills necessary to go up against Toussaint Louverture.

      I wonder what those skills, specificially, are. The fact that so many successful politicians come from the ranks of entertainers and writers makes me think politics is more – and this is a weird word – artistic?

      1. Hey Ben,
        I’m not sure the people skills are all that different. Again, I think it’s more possible in business and the military to makeup for deficiencies in people skill with technical skill, to at least some extent. That and the people skill competition is probably most intense at the political level.

        I think about someone like Dwight Eisenhower. The secret to his rise to be Allied Commander in WWII was in knowing how to handle egotistical generals, many of whom were probably far more proficient than him in actual military tactics. I haven’t studied George Washington in detail, but from what I’ve heard, there was a similar dynamic going on.

        If you read the biographies of Abraham Lincoln and FDR, you’ll see similar patterns. They knew how to keep their own ego in check, particularly at key junctures, while soothing, or at times manipulating the egos of other powerful people.

        What are the skills? I think you can get insights into them by reading Dale Carnegie’s ‘How to Win Friend and Influence People’, Sun Tzu’s ‘The Art of War’, and Machiavelli’s ‘The Prince’, but also biographies of the people mentioned above. (Ancient biographies, unfortunately, usually aren’t as useful for this, since alternate viewpoints of those involved are typically lost.)

      2. Hey thanks for the recommendations. I’m really interested in the ways power works and, actually, I got started on this road when I read The Art of War. Machiavelli is a hero of mine, as well, though I prefer Discorses on Titus Livinius. I’ll have to look into Carnegie. 🙂

      3. Another good resource is Robert Caro’s mind numbingly detailed biographies of Lyndon Johnson. Johnson is, of course, remembered for his failing as much as his power, but his rise and use of power in the Senate and Presidency were extraordinary.

      4. Ooh, definitely this is on the list. Everything I’ve heard about LBJ makes me think he’s a fascinating dude. Thanks.

  2. I must be slipping, I find nothing to debate in this post. I would add that in the instance of Haiti we see evidence that winning freedom for, and turning the task of self-governance over to, a people who have no history of governing themselves is doomed to failure. In my opinion the learning curve is too steep to master during the period that the left over resources will remain. They will soon begin to eat the seed corn. Although there are many, another example would be Rhodesia.

    1. Haiti is such a sad story.

      I really recommend you look into Toussaint Louverture. The guy was most definitely an autocrat, but when the French assasinated him I truly believe they doomed the island.

      This all begs the question, however, of how any democracy gets started.

  3. I’m no stranger to Louverture and Haiti is indeed a sad case. As is too often the situation, when a colonial power pulls out (for whatever reason) and leaves a power vacuum it is usually filled by proactive opportunists who then use the country as their personal cash cow. This results in a monolithic governing structure which will seek to crush all attempts at power sharing by the populace. Benevolent dictators are few and far between. Democracy, it would seem, must have its origins in a collective of some sort, sharing authority from the very beginning and inviting participation from all willing to add input.

    1. That’s a hard balance to achieve. I wrote a letter to Mohsin Hamid, my favorite living author, about this. You might be interested in it.

      How did you come across Louverture, if you don’t mind?

  4. […] of my consciousness. I’ve had the privilege to learn from an amazing Kenyan professor and Toussaint Louverture is one of my favorite people in history. There are a lot of black men like them who absolutely […]

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