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So in the book Brothers in Arms in Bujold's Vorkosigan Saga, in one of the conversations real-Miles tried to convince alter-Miles that it's impossible to pretend to be admiral Naismith:

"You still couldn't bring it off," argued Miles. "There are five thousand Dendarii. I know hundreds of them by name, on sight. We've been in combat together. I know things about them their own mothers don't, not in any log. And they've seen me under every kind of stress. You wouldn't even know the right jokes to make.

Was Miles exaggerating to dissuade his captors from using his people? If not, how come he knew that many people well? Dunbar's number places our cognitive limit at 150, not a few hundred...?

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Probably. This is Miles, after all, who is not only prone to telling tall tales (e.g. how he wound up with the Dendarii in the first place), but also expects the impossible from himself (and often gets it), and one of his fatal flaws is that he's so convinced he can do anything that he can fall very flat when it turns out he can't do something.

That said, Dunbar's number isn't an absolute. It can be overcome with proper compartmentalization. Miles probably doesn't know everyone's details intimately, but he has a wide variety of information about the key individuals, and trivia about a lot of the rest. And past that, he probably fudges the details, using his mythical attention to details to convince people he knows them like a brother.

As regards organizational efficiency, the real point of Dunbar's studies, he does a lot of delegating to senior officers. And honestly, there is inefficiency. He has a mutiny on his hands the second time he meets up with them, and he's fairly certain they'll disintegrate under their own weight when he leaves.

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    More telling is that hundreds of Dendarii know Admiral Naismith. Miles himself might not remember everything and everyone, but one of those hundreds may recall something about Naismith that "fake Naismith" can't know or just doesn't do. Hmmm. "Fake Naismith." Do two fakes make a real? Naismith himself is just an act Miles does. – JRE Jan 4 at 12:29
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    In a military organization, compartmentalization is standard. In addition, the claim was "hundreds of them by name, on sight" not hundreds for which "I know things about them their own mothers don't". (Also, the plural "hundreds" is used for numbers over 100 but less than 200.) Miles has an obsession with personal loyalty (coming from both his father and mother, along with Barayar's fealty tradition). – Paul A. Clayton Jan 4 at 12:31
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    Also from "Borders of Infinity": "The faces, names, voices of the six familiar Dendarii fluttered through his memory. The 200 ciphers must have had faces too. He blocked them out, as too crushing an overload." While he would have reasons to be more familiar with the shuttle crews (and other crew going off ship as well as medicos that never leave their ships while on duty), this indicates he recognized 42 (14 shuttles, 3 crew each) non-direct reports. – Paul A. Clayton Jan 4 at 12:31
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    @JRE - Honestly, I think Naismith is a bit more than an act. He certainly started as an act, but his later adventures make it clear that he falls into Naismith effortlessly. I wouldn't go so far as to call him a distinct, separate personality or anything, but I think he's more than just an act. – RDFozz Jan 4 at 16:16
  • It's kind of like the question of whether Bruce Wayne plays Batman, or Batman plays Bruce Wayne. – FuzzyBoots Jan 6 at 15:12

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