In Demosthenes’ speech “Against Zenothemis”, we are led to believe that two rogues, Zenothemis and Hegestratos, had devised a scam taking advantage of the usual terms of maritime contracts that if the ship was lost they would not have to repay the money they had borrowed to fund their trading voyage. I find it incredibly difficult to believe that anyone would try to sink a ship when they were far out to sea and they were on board – or that they could possibly have got away with it. It seems that merchant ships towed a small boat behind them which is what they would have hoped to escape on. Anyway this is what Demosthenes wrote.
On taking the money, they sent it home to Messalia, and loaded nothing on to the ship. Because there was a contract, just as is usual with all contracts, that they would repay the money only if the ship was saved, they plotted to sink the ship in order to defraud the lenders. Hegestratos accordingly when they had sailed two or three days from land, went down during the night into the hold of the boat and started to cut away the bottom of the boat. Zenothemis, acting as if he knew nothing about it, stayed upstairs with the rest of the passengers. But because of the noise, those in the boat realised that something bad was going on in the hold and went down to help. Hegestratos, as he was caught red-handed and suspected that he would pay the penalty, tried to escape, and during the chase threw himself into the sea, but missing the ship’s boat he was drowned. So he died badly, as befits a bad man, suffering himself what he had planned for others.
λαμβάνοντες δὲ τὰ χρήματα, οἴκαδ᾽ ἀπέστελλον εἰς τὴν Μασσαλίαν, καὶ οὐδὲν εἰς τὴν ναῦν εἰσέφερον. οὐσῶν δὲ τῶν συγγραφῶν, ὥσπερ εἰώθασιν ἅπασαι, σωθείσης τῆς νεὼς ἀποδοῦναι τὰ χρήματα, ἵν᾽ ἀποστερήσαιεν τοὺς δανείσαντας, τὴν ναῦν καταδῦσαι ἐβουλεύσαντο. ὁ μὲν οὖν Ἡγέστρατος, ὡς ἀπὸ τῆς γῆς ἀπῆραν δυοῖν ἢ τριῶν ἡμερῶν πλοῦν, καταβὰς τῆς νυκτὸς εἰς κοίλην ναῦν διέκοπτε τοῦ πλοίου τὸ ἔδαφος. οὑτοσὶ δ᾽, ὡς οὐδὲν εἰδώς, ἄνω μετὰ τῶν ἄλλων ἐπιβατῶν διέτριβεν. ψόφου δὲ γενομένου, αἰσθάνονται οἱ ἐν τῷ πλοίῳ ὅτι κατόν τι ἐν κοίλῃ νηὶ γίγνεται, καὶ βοηθοῦσι κάτω. ὡς δ᾽ ἡλίσκεθ᾽ ὁ Ἡγέστρατος καὶ δίκην δώσειν ὑπέλαβεν, φεύγει καὶ διωκόμενος ῥίπτει αὑτὸν εἰς τὴν θάλατταν, διαμαρτὼν δὲ τοῦ λέμβου διὰ τὸ νύκτ᾽ εἶναι, ἀπεπνίγη. ἐκεῖνος μὲν οὕτως, ὥσπερ ἄξιος ἦν, κακὸς κακῶς ἀπώλετο, ἃ τοὺς ἄλλους ἐπεβούλευσε ποιῆσαι, ταῦτα παθὼν αὐτός.
Demosthenes – Against Zenothemis 5