#10 Isaac Vail

Isaac S. Vail (1835-1905), aka Old Ike — Confidence Man, Pickpocket

From Byrnes’ text:

DESCRIPTION. Fifty-one years old in 1886. Born in United States. Married. Slim build. Height, 5 feet 11 inches. Weight, 178 pounds. Gray hair, brown eyes, light complexion, gray whiskers. Generally wears a goatee. A tall, thin, gentlemanly-looking man.

RECORD. Ike Vail is well known from Maine to California. Of late years he has confined himself to the eastern cities, and the confidence man may be seen almost any morning around railroad depots or steamboat landings in search of victims. He has done service in several prisons, and his history would fill an ordinary-sized book. I will simply give one or two of his later convictions, to assist in convicting him should he fall into the meshes of the law again.

Vail was arrested in New York City on February 20, 1880, for swindling one Levi P. Thompson, a Justice of Peace of Evensville, Minn., out of $60, by the confidence game. He pleaded guilty in this case, in the Court of General Sessions, New York City, and was sentenced to eighteen months in State prison by Judge Cowing, on February 26, 1880. Vail was arrested several times afterwards in Boston, New York, and other cities, and again in New York City on August 30, 1885, for attempting to ply his vocation on the steamer Glasgow, lying at Pier 20, North River. For this offense he was sentenced to six months in the penitentiary on Blackwell’s Island, on a complaint of vagrancy, as he had obtained no money from his victim. He was, however, discharged by Judge Van Brunt in the Supreme Court, on a writ on September 4, 1885. Vail’s picture is an excellent one, taken in 1880.

Isaac S. Vail was born on September 20, 1835, to a successful farming family, his parents being Joseph and Sarah Ann Vail of Hughsonville, New York (near Fishkill in Dutchess County). According to Isaac, he left home at age fifteen because his father refused to send him to school. Isaac drifted west across the state to Niagara Falls, where he found work as a hostler (stable lad) of the Table Rock House, which overlooked the Horseshoe Falls. One night in January, 1856, when he was twenty years old, Isaac went out drinking with some friends. They journeyed from tavern to tavern, getting increasingly drunk. On their return to the stable bunk office, he and his two companions started to argue; one of then, John Ryan, attacked Vail. Vail grabbed a stick and beat Ryan off, cracking his skull. Ryan died from the injury.

Vail was not convicted of murder, having acted in self-defense; but he did lose his job, and later found work as a railroad brakeman. He came into contact with men leading transient life-styles, one of whom he named as Old John King, “the founder of modern swindling.” [Either’s King’s fame was very limited, or Vail chose to assign this as an alias–other references to a famed confidence man named John King have not been found.] From “Old John King”, Isaac Vail learned the various scams used by confidence men of that time. By the mid-1860s, Isaac Vail started to be recognized as a professional con artist.


By later standards, Ike Vail was a grifter–a practitioner of “small cons,” meant to separate the victim from his ready cash quickly; and requiring no skilled partners or no partners at all. In a pinch, he would cut to the chase and simply pickpocket his victim. Over the decades from the 1860s through the 1880s, Ike was credited with inventing many standard scams, including: “the lottery game,” “the checks game,” “the send game,” and “the prize package”; all of these were forerunners of the “gold brick” and “green goods” games that dominated the 1880s and 1890s.

In 1888, the New York World published an account of one of Ike’s scams and his arrest that typified his modus operandi:


The same characteristics that helped to hoodwink his victims: his fine dress, tall frame, and well-spoken diction–also served to stand out his presence to police. In 1903, at age 67, he complained to an interviewer:

“It’s an easy thing for young fellows starting in to graft as compared to the old timers. Nobody knows them as professionals and if they are caught at all, they stand a good show of beating the case. Of course, practice in any profession makes perfect, but what is the use of it when you face gets to be  as well-known as the Astor House or any other old landmark?…with the years, my circle of acquaintances has gradually widened until now you can find my photograph in nearly every city from Maine to ‘Frisco. I’m an easy mark for the cops once they get my description,  because of the two moles between my eyebrows. There’s no way of disguising them and they seem to grow more prominent every year. Another thing: while my appearance is in my favor among strangers in New York or Boston, I am too distinguished in appearance not to attract attention in most other towns.

“Another thing: there’s more science in graft now than there used to be, and we old fellows are behind the times. The young men have new schemes that are more attractive than anything we can offer…The young men have the nerve and the confidence, that have grown weaker in the old men with every arrest and prison sentence. Many of their schemes are so clever that the law can’t touch them, and they generally work in bunches.”

It is startling to hear a con-man speak the word “confidence” in relation to the attitude of the swindler, not the credulity of the victim–and moreover to admit that he, as an aging confidence artist, had lost some of that quality.

Two years later, in 1905, Ike had lost the ability to support himself, and asked a nephew living in the Bronx for shelter. Ike died in his nephew’s house, and his body was conveyed back to Dutchess County. Isaac S. Vail was buried in the same plot as his parents, and his name appears on the same memorial stone alongside the father that spurned his son’s desire to be educated.


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s