Let me, for one, say that I am very skeptical of Spartan generalship if Gylippos the Mothrax—the victor of Syrakusa—is unable to think through the game tree to understand that there is probably, somewhere, an accounting check on his actions.
"Not knowing there was a writing in [each] sack indicating the sum it held" is not a boss move here:
Plutarch: Life of Lysander http://penelope.uchicago.edu/Thayer/E/Roman/Texts/Plutarch/Lives/Lysander*.html: 'Lysander, after settling these matters, sailed for Thrace himself, but what remained of the public moneys, together with all the gifts and crowns which he had himself received,—many people, as was natural, offering presents to a man who had the greatest power, and who was, in a manner, master of Hellas,—he sent off to Lacedaemon by Gylippus, who had held command in Sicily. But Gylippus, as it is said, ripped open the sacks at the bottom, and after taking a large amount of silver from each, sewed them up again, not knowing that there was a writing in each indicating the sum it held. And when he came to Sparta, he hid what he had stolen under the tiles of his house, but delivered the sacks to the ephors, and showed the seals upon them. When, however, the ephors opened the sacks and counted the money, its amount did not agree with the written lists, and the thing perplexed them, until a servant of Gylippus made the truth known to them by his riddle of many owls sleeping under the tiling. For most of the coinage of the time, as it seems, bore the forgery of an owl, owing to the supremacy of Athens. Gylippus, then, after adding a deed so disgraceful and ignoble as this to his previous great and brilliant achievements, removed himself from Lacedaemon...
Of course, what can we say about Athenian demagogue and general Nikias, who was beaten by Gylippos?