Michael Ostrog And The Art Of The Scam

Michael Ostrog is one of the names that appeared on Melville Macnaghten’s list of three men who were likelier than Thomas Cutbush to have been Jack the Ripper.

Michael Ostrog was a nasty piece of work – he was a liar, a cheat, a conman and a petty thief.

But, in his long career – which was chronicled almost religiously by the Victorian newspapers – the one thing that he never was was homicidal.

In fact, the only times that Ostrog ever resorted to violence was to either evade capture or to escape from custody once he had been captured.

Aside from those occasions, he just doesn’t seem a likely contender for the mantle of the Whitechapel murderer.

A portrait of suspect Michael Ostrog.
Michael Ostrog – The Fashionable Rogue


However, as a conman, he was relatively skilled and could ingratiate himself into the company of a wide variety of dupes or marks in order to relieve them of money and possessions or to scrounge hospitality from unsuspecting hosts.

Innkeepers, tradesmen, schoolteachers, soldiers, doctors and vicars were among the many victims of Michael Ostrog – and most of them could not be described as having been stupid or unintelligent, so they were not the type of people that you would think of as being easy to scam.

But, con them Michael Ostrog did.

In this article, I don’t want to so much look at Ostrog’s potential as a Jack the Ripper suspect, but rather, I want to consider how the man – who one newspaper described as “a fashionable rogue” – managed to win the confidence of his victims in order to cheat them and to rob them.


The important thing to establish about Micahel Ostrog is that he must have been an absolute charmer, and in this lay his danger to others.

To be effective as a con man he would have had to win his victims over and establish a rapport with them to put them at their ease and encourage them to let their guard down.

In his 1940 book, The Big Con: The Story of the Confidence Man, David W. Maurer has this to say about the psychology of a successful scammer:-

“The grift has a gentle touch. It takes its toll from the verdant sucker by means of the skilled hand or the sharp wit. In this, it differs from all other forms of crime, and especially from the heavy-rackets. It never employs violence to separate the mark from his money. Of all the grifters, the confidence man is the aristocrat. Although the confidence man is sometimes classed with professional thieves, pickpockets, and gamblers, he is really not a thief at all because he does no actual stealing. The trusting victim literally thrusts a fat bank roll into his hands. It is a point of pride with him that he does not have to steal. Confidence men are not ‘crooks’ in the ordinary sense of the word. They are suave, slick and capable. Their depredations are very much on the genteel side.”


Michael Ostrog was, most certainly, suave, slick and capable.  Indeed, many of the newspapers that published articles about him seem to have seen him as a romantic figure.

The Pall Mall Gazette, for example, had this to say about him, in an article that appeared on Saturday 4th October 1873:-

“He appears, by all accounts, to be a most gifted and fascinating person, and quite an ornament to the class to which he belongs…”

The Illustrated London News began an article about him by describing him as:- “a criminal of an interesting and desperate type…”

Evidently, the Victorian press was quite impressed by Ostrog’s “skill” as a scammer, so I thought it might be intriguing to look at just one of Ostrog’s many escapades and compare the way he did it with classic behaviour of a successful grifter.


In his book Catch Me If You Can; The True Story Of A Real Fake, Frank W. Abagnale observes that:-

“Top con artists, whether they’re pushing hot paper or hawking phoney oil leases, are well dressed and exude an air of confidence and authority. They’re usually as charming, courteous, and seemingly sincere as a politician seeking reelection, although they can, at times, effect the cool arrogance of a tycoon.”

The first fallacy to dismiss concerning the victims of con artists is that they must have been stupid for allowing themselves to be conned.

This is certainly not the case. According to <em”The Big Con, “It is not intelligence but integrity which determines whether or not a man is a good mark…dumber people are often more difficult to con than smart people:-

“Stupid or “lop-eared” marks are often played; they are too dull to see their own advantage, and must be worked up to the point again and again before a ray of light filters through their thick heads. Sometimes they are difficult or impossible to beat…”


In 1864, using the alias of Count Sobieski, Ostrog turned up in Bishop Stortford where he introduced himself to a respectable local tradesman.

The first thing a confidence trickster must do is create empathy and rapport: an emotional foundation must be laid.

And, as can be seen from the following article, which appeared in The Chelmsford Chronicle, on Friday, 12th February, 1864.

According to the article, Ostrog introduced himself as:-

“the son of a fallen Polish nobleman, and himself a personage no less than Count Sobieski, who had made his escape from Warsaw after being sentenced, like his parent, to end his days at Siberia, and that he was then travelling to Cambridge to meet some countrymen who were pursuing their studies at the university.”


A good con man will begin by putting his victim at ease by telling stories that reveal his own anxieties, thus fabricating what feels like common ground. They are “confidence men” for a reason. They exude confidence, gain your confidence, and then exploit that trust, and this is exactly what Ostrog did with the tradesman.

Next, the confidence man must get a foot in the door.

Obviously, if they ask for a large favour straight away, the victim’s defences will go up. So, it is imperative to start small, and Ostrog (or in this case Count Sobieski), as the newspaper revealed, had soon got his foot in the door by informing the tradesman that:-

He required hotel accommodation, “not grand,” he remarked, as his means were limited, but they must be cleanly, and at the same time displaying all the money which he said he possessed, 1s. 8d.”


His approach was successful, as the newspaper continued:-

“The tradesman was at once “gulled;” he left his business personally to introduce the “Polish Count” to the keeper of the adjoining hostelry.”

Here, Ostrog is demonstrating one of the deadliest weapons in the con artists arsenal social proof. People are more likely to do things if they see other people doing them first; You’re more likely to friend a stranger on Facebook if the two of you have mutual friends.

As Robert B. Cialdini puts it in his book  “Influence: The Psychology of Persuasion” puts it:-

“People rely on social cues from others on how to think, feel, and act in many situations. And not just any people, but peers. People they believe are similar to them. This is a key point and what is called social proof.”

Had Ostrog simply turned up at the neighbouring hostelry, the landlord would, no doubt, have been on his guard; but, by first “gulling” the tradesman and then persuading him to make the introduction, Ostrog was able to instantly win the trust of the landlord.


And, boy oh boy, did the landlord trust him – as can be seen from the next passage in the newspaper article:-

“The Count Sobieski’s plausible manner and pitiable tale also at once touched the sympathies of mine host of the Coach and Horses, and all the house afforded – the choicest fare, solids and fluids, with the best spare bed – fell to the lot of the “unfortunate exile,” with the following day “nothing to pay,” a hearty shake of the hand, and a piece of gold left in the palm, to help him on the road to classic ground.”


A good confidence trickster has to be an excellent actor, and Ostrog was evidently a performer par excellence.

Having now established himself as Count Obieski, in the minds of two respected local citizens, he was able to use their trust to win the trust of other locals. Having left the Coach and Horses:-

“The “Count” was not ungrateful, so he turned his thoughts to the tradesman – his first acquaintance – to thank him, and also to make known the generosity of his late entertainer; however, in this shop at the time were two professional gentlemen, and with whom somehow or other the “Count” got into conversation, which ended by his being requested to become the guest of one of them.

Of course, the exile somewhat desired to meet his “dear friends at Cambridge,” but notwithstanding this obstacle consented.

His melancholy story, well-bred and amiable manners, again made a friend in the mistress as well as the master, and he became “the star of the house” for four days, when he “reluctantly tore himself away,” but not without taking further opportunity of adding to his obligations by the loan of two or three “leetle sovereigns,” the gentleman obligingly going to the railway station, at his request, to procure a first-class ticket for Cambridge, the count fearing he could not make “de mon understand.”


Having persuaded his victim to pay for a first-class ticket to Cambridge, Ostrog headed to Cambridge where he managed to con a man named Draper, of Magdalen College and, the next day, he  to Bishop Stortford to once more stay with his “friends” with whom he was only too happy to attend church on the following Sunday.

But even here he couldn’t resist a quick con, as the article went on to report:-

“…he was informed a collection would be made for repairing the building, and, wishing to be a contributor, he borrowed “one” piece of silver from his friend, for the purpose being a “charitable Christian.”


It is worth noting that when he next returned to Cambridge, a few days later, Mr, Draper had become suspicious of him, and on stepping off the train, Ostrog was arrested by the police and, at his following court appearance he was sentenced to three months in prison.

Michael Ostrog would go on to con more people in cities all over England over the next twenty years.

In fact, almost every time he committed a con or a theft he was caught, and, in consequence, he spent long periods in prison.

But, the one thing that comes across time and time again when reading accounts of his various escapades, is that prison appears to have done nothing to have curbed his skill at spotting a dupe and worming his way into their trust.

In consequence, the life story of Michael Ostrog is an intriguing one and is worth studying as a lesson to us all that an Ostrog type of character could turn up in our lives at any time, so by understanding his methods we might be able to protect ourselves.