Picture a man frantically sawing through the bottom of his own ship in the middle of the Mediterranean Sea. Passengers rush below deck to find him red-handed, hole half-cut, wood shavings floating in the rising water. A chase ensues. The would-be fraudster, cornered and desperate, hurls himself into the ocean rather than face justice.
This isn’t a Netflix true crime series; it’s a 2,300-year-old insurance fraud that went spectacularly wrong.
In the latest episode of Oh My Fraud, host Caleb Newquist takes listeners on a journey through time to explore some of history’s earliest recorded financial frauds. Fresh from his European travels (with a particular fondness for Budapest’s goulash and Vienna’s coffeehouse culture), Caleb digs into ancient schemes that prove creative accounting isn’t a modern invention.
When Rome Literally Auctioned Off the Throne
The Year of Five Emperors in 193 reads like a corporate governance nightmare. It started with Emperor Commodus getting assassinated on New Year’s Eve 192 and creating what Caleb calls “quite an exciting start to the year 193.”
His successor, Pertinax, took the throne with big plans to reform Rome’s finances, which Commodus had left in ruins. Think of him as the turnaround CEO brought in after a spending spree. His first move was cutting the donativum, the cash gifts emperors traditionally paid to the Praetorian Guard when taking power.
Bad idea. The Praetorian Guard, Rome’s elite military unit responsible for protecting the emperor, didn’t appreciate their bonus getting slashed. When Pertinax’s follow-up offers still fell short, around 300 guards stormed the palace. After what Caleb imagines as “a very brief conversation,” they assassinated him. His entire reign: 87 days.
What happened next defies belief. The Praetorian Guard auctioned off the throne to the highest bidder. Marcus Didius Julianus won and became emperor, essentially purchasing the Roman Empire like buying a company at auction. But word quickly spread about how he got the throne. Three influential generals rebelled and claimed it for themselves. Within 66 days, Julianus was assassinated, ending one of the shortest reigns in Roman history.
The parallels to modern corporate fraud are hard to miss. We’ve seen executives obtain positions through financial manipulation and insider dealing. The donativum system itself mirrors modern bonus structures that create dangerous dependencies. When those bonuses get cut, whether in ancient Rome or on Wall Street, the backlash can destroy companies and careers.
The World’s First Insurance Fraud Goes Sideways
If the Roman story shows political corruption at its worst, ancient Greece produced the world’s first recorded insurance scam in 360 BCE. Meet Hegestratos, a sea merchant with a plan that was elegant in its simplicity and spectacular in its failure.
To understand the scheme, you need to understand bottomry loans. Back then, sea travel was genuinely terrifying. Ships sank all the time. Bottomry allowed merchants to borrow money using their ship and cargo as collateral. If the vessel reached its destination, the merchant sold the cargo, repaid the loan with interest, and kept the profit. If the ship sank, the lender ate the loss. It was proto-insurance built on trust that merchants wouldn’t deliberately sink their own vessels.
Hegestratos saw opportunity where others saw protection. He and his coconspirator Zenothemis took out a bottomry loan for a grain shipment from Syracuse to Athens. But instead of using the money properly, they immediately sent it to Massalia (modern-day Marseille). They planned to sail for a few days, scuttle the ship, claim tragic loss at sea, and keep both the loan money and the grain.
Two or three days into the voyage, Hegestratos decided it was showtime. He snuck below deck and began cutting a hole in the ship’s hull. Meanwhile, Zenothemis stayed topside, supposedly creating a diversion.
But as Caleb hilariously reimagines it, Zenothemis was terrible at his job. Picture him “fake coughing every time there’s a loud noise from down below” while other passengers, who already didn’t like him, grew suspicious. The cutting was loud. The diversion was pathetic. Soon, passengers rushed below to find Hegestratos literally caught red-handed.
What followed was pure slapstick. Caleb envisions it as “one of those Keystone Cops chase scenes with Yakety Sax playing behind it.” Hegestratos flees through the ship, passengers in hot pursuit, ending with the fraudster hurling himself into the Mediterranean. As the ancient orator Demosthenes recorded, “Thus miserable as he was, he met a miserable end as he deserved, suffering the fate which he proposed to bring about for others.”
You’d think watching your partner drown would inspire some soul-searching. Not Zenothemis. With remarkable audacity, he tried to continue the fraud. He actually asked the crew to sink the ship anyway, arguing that “all hope was lost.”
When that failed and they limped to shore at Cephallenia, there was a dispute. Protus, the “supercargo” responsible for the grain reaching Athens, wanted to continue there. Zenothemis insisted they go to Massalia, claiming connections to the deceased fraudster and the original lenders. The local magistrates sided with Protus. They ordered the ship to Athens, where Zenothemis filed lawsuits claiming ownership of the grain.
The Mystery Ending That Still Bugs Historians
The frustrating part of this story is we don’t know how it ended. The original documents were “mutilated,” leaving only 32 paragraphs that “yielded no satisfactory sense” about the final verdict.
This uncertainty has sparked debate for centuries. John M. Zane’s 1925 Michigan Law Review analysis offers a twist: maybe Zenothemis wasn’t a coconspirator but another victim. Zane points out that Zenothemis had no access to the redirected money, no legitimate claim to sell the cargo, and nothing to gain from the ship sinking. Maybe he desired to return to Massalia because he genuinely wanted to collect insurance to repay his lender friends.
Zane even suggests that if it went to trial, the rich lenders probably lost because Athenian juries were populist and unsympathetic to wealthy plaintiffs, a dynamic that sounds familiar to anyone following modern white-collar crime prosecutions.
Whether Zenothemis was a fraudster or a fool, the case establishes a principle fundamental to financial law: fraudulent contracts are void. This ancient precedent echoes through centuries of case law and continues protecting victims today.
Ancient Schemes, Modern Lessons
As Caleb notes, there are no new frauds, just new fraudsters. The schemes evolved from bottomry loans to blockchain, from cutting holes in ships to cutting corners in compliance, but the patterns remain:
- Exploiting trust. Bottomry loans worked because people trusted merchants wouldn’t sink their own ships, just as modern systems assume executives won’t tank their own companies
- The coconspirator problem. Hegestratos learned fatally that complex fraud needs help, yet every additional conspirator multiplies detection risk
- Documentation dilemmas. Even in 360 BCE, fraudsters needed false paperwork and had to manage competing claims
- Greed override. Both cases show how easy money overrides rational risk assessment
Caleb’s observation about creating diversions particularly resonates: “You cannot have any weak links in your conspiracy. Don’t think you can just let some hack create a half-assed diversion for you.” His reimagining of Zenothemis’s pathetic distraction attempts—fake coughing to cover ship-cutting sounds—reminds us that fraud often fails not in conception but in execution.
For CPAs and fraud examiners, these aren’t just historical curiosities; they’re training exercises in pattern recognition. The executive inflating revenues for bonuses follows Julianus’s playbook. The insurance fraudster staging accidents mirrors Hegestratos’s scheme. Understanding these patterns helps professionals spot red flags before they become scandals.
The Timeless Blueprint of Financial Deception
From emperors buying their positions to merchants attempting insurance fraud, these ancient cases reveal that financial deception is as old as commerce itself. The schemes involved ships instead of spreadsheets, cargo instead of cryptocurrency, but the underlying patterns of exploiting trust, creating false documentation, and letting greed override judgment haven’t changed.
For today’s accounting professionals, these historical frauds serve as cautionary tales and educational tools. That executive oddly eager to bypass controls? They’re following Julianus’s playbook. That unusual insurance claim with convenient timing? It echoes Hegestratos’s bottomry loan scheme. The vendor insisting on redirecting payments? They’re pulling a move as old as Massalia.
What makes these ancient frauds valuable is their stripped-down simplicity. Without modern financial instruments and digital smokescreens, we see the raw mechanics of deception. The Praetorian Guard’s throne auction isn’t fundamentally different from a board being bought off; it’s just more honest about the transaction.
Listen to the full episode of Oh My Fraud to hear Caleb bring these ancient frauds to life with his signature blend of historical detail and irreverent humor. Because sometimes the best way to understand today’s financial crimes is to study the fraudsters who wrote the original playbook over two millennia ago.