soldier with rifle american civil warTHE HORSEMAN©





When the decade of the Twenties began, Jack Ryan held an established place in the fraternity of gamblers that managed the national business of horse racing and gambling clubs. By its end he was down to his last friend—John W. Considine—and his last dime. Like his life through the Gay Nineties and early 1900s, it was an exciting ride, with rushes to the crest and swoops to the bottom and up in the dough again and out again.

At the time of the Dempsey-Willard fight in Toledo, the Michigan Legislature had passed a law in anticipation of the Volstead Act that prohibited the sale of alcohol, which immediately attracted the interest of Jack's crowd, many members of which operated gambling clubs in major cities whose patrons expected to drink liquor. The gamblers reacted to prohibition by organizing a distribution network for liquor imported, first, from Cuba, and later from Canada.

From the available evidence it appears probable that Jack was an active participient in setting the network up between Detroit and St. Louis and cities in between. As early as 1919, Jack appears as the ostensible owner of a cattle farm located a few miles north of Toledo, in Temperance, Michigan. Temperance became a major depot in the movement of alcohol southward from Detroit and it is obvious that posing as a cattleman gave Jack's participation in its distribution good cover. The record of his passport applications reinforce this impression, as it shows he made a series of trips, via Key West, to Cuba in the early years of the decade.

St. Louis Post Dispatch, 1916

As the newspaper piece reflects, Jack's earliest visit to Cuba appears to have been in 1916 which coincides with the opening there of a race track and casino built by H.D. (Curley) Brown, a man connected with the management of a number of eastern tracks in existence at the time and, later, with the City Park racetrack that, in the early twenties, opened in New Orleans, and with the Arlington track that opened about the same time in Chicago. Given the fact that Jack acted often as the front man for a group of gamblers, each with a separate base of operation, it is probable his early Cuba visits were focused on race track and casino gambling ventures the group invested resources in—Jack's job being to manage the group's investment in a manner that resulted in profit. As prohibition entered the picture, Jack's assignment probably broadened to include making arrangements for the movement of alcohol from Cuba to the United States. Given the fact that, while Cuba exported ever increasing amounts of grain alcohol in the Twenties, as well as sugar and tobacco, it never exported alfalfa, it must be assumed Jack used the alfalfa gimmick, in his visit to St. Louis in 1916, as his public excuse for being there. The real reason must have been to renew his old connections to the St. Louis's Irish mob which included his old crony, Carmody, who operated a string of saloons at this time.

anna letter

Anna's Letter to Jack 1918

cattle car
Detroit Free Press September 1919

Havanna's Oreinti Race Track, circa 1920

New York Times, 1921

In 1921, with full national prohibition in effect, Jack came to St. Louis in a steam yacht, the Kalolah. With him was Flora, the twenty-five year old girl from Kentucky he had left his wife for, in 1917, and a crew composed of several supposed Hawaiians. The ostensible purpose of his visit was to promote the organization of a barge business between New Orleans and St. Louis, but this, like the John J. Ryan Cuban-American Alfalfa Co. of 1916, was probably a cover for his involvement as go-between in the alcohol distribution scheme. Indeed, who knows whether the yacht was loaded with booze for delivery to the St. Louis mob.


st louis paper

St. Louis Post-Dispatch Oct. 7, 1921

St. Louis Post-Dispatch, Oct. 7, 1923

Wherever else he may have had operations, it seems that between about 1921 and the fall of 1923, he owned and operated a boarding house in Downington, PA which may have played a role in the Irish mob's liquor distribution network as well as provided a cover for gambling activities.

In September 1923, Anna came to Downington. She was dying, and she asked Jack to remarry her and he did. She died in October and he took her remains to St. Louis, for burial in Calvary Cemetery where her mother and father and all her sisters and brothers are buried. Jack had married Anna in St. Louis, in 1886, and the two enjoyed together three wild decades in which they traveled the world, lived in large expensive homes, had three children; and then, when Jack abandoned the boat business with Chris Smith, he abandoned Anna, and went off to the East Coast with Flora, a woman half his age, who remained with him to his last end.

Petition to Set Aside Divorce and Reinstate Marriage

Detroit Free Press

St. Louis Globe-Democrat

After Anna's death, Jack returned to Detroit and, after a short time operating on his own, he joined with his son-in-law, George Weinbrenner, and Weinbrenner's partners, Danny Sullivan and Lincoln Fitzgerarld, in their gambling operation. His role was the management of a gambling den that came to be publically known as "Jack's Place," located at 21 West Elizabeth Street in the Grand Circus Park area of downtown Detroit. You walked in from the street and found yourself in a cigar store. Given the once over, if you were approved, you were directed to a metal door in what appeared to be the rear of the store. A peep hole opened and you were given the once over again; at which point the door opened and you were passed into a hallway that led to another metal door. This opened, you passed into a large room filled with gambling paraphernalia—a crap table, roulette wheel, card tables and chairs, and a bar. There was a steel pulpit attached to one wall, with a man standing in it with a tommy gun. As you put your money down at the tables and drank your liquor and the time passed, you would become a little sloppy and be receptive to the suggestion to take a free ride with your pals up Gratiot Ave, to the Chesterfield Inn in East Detroit, just over the Wayne County line in MaComb County where the police and the DA were in on the take. Given your state of inebriation, it didn't occur to you to inquire how and when you would get back.

Detroit Free Press, December 1923

Detroit Free Press, Feb 1924

Detroit Coppers Posing in Jack's Place

Between February 1923 and the summer of 1925, Jack's place was raided over a hundred times. Most of these raids resulted in no charges, because by the time the police were able to bust their way through the several metal doors and gained entrance into the gambling room, the cards, dice, chips and roulette wheel were gone. The room was full of men but with no visible sign of actual gambling going on, no legal basis existed to charge anyone, and, in any event, Jack was never present to be arrested. It was always someone else arrested.

Jack's Place as it exists today

Type of Transportation Ryan Used to Move
Customers to the Chesterfield Inn

Chesterfield Inn, circa 1924

Lincoln Fitzgerald, George Weinbrenner, and Danny Sullivan
Jack's Detroit business associates

The Purple Gang
Protectors of Ryan and Associates 1923-25

Detroit Free Press, August 1923

Detroit Free Press, Feb. 1924

Detroit Free Press, Feb. 1925

Downtown Detroit Gambling Zone, circa 193-25

Detroit Free Press, May 1925

In 1925, the Michigan Legislature passed a law that allowed the Detroit police to picket notorious gambling dens with officers who were empowered to stop anyone attempting to enter the establishment. At the same time, Italian gangs were becoming a serious nusiance, engaging in gun battles in the broad daylight in the streets. Up to this point, the Jews of the Purple Gang had provided the gamblers with protection, manning the doors of their joints and preventing robberies. But the Italians were bringing a new game to town and the warfare going on seems to explain why Jack left Detroit in July 1925 and, with Flora, went to Cincinnati where he took possession of a Lincoln town car from a dealer, giving him a note supposedly payable by his brother Ed, and drove to El Paso, Texas. It is not clear why, but George Sadlo, who later would front for the mob in the management of the Thunderbird Casino in Las Vegas, made El Paso his home base and had been connected in business with Jack since at least 1914.

1918 Ryan divorce Declaration

El Paso Times, 1923

Brownsville Herald, 1931

Thunderbird, Las Vevas, circ 1955

Jack arrived in El Paso in September 1925 and was arrested at a gas station by a federal officer, on the charge of violating the Mann Act: he traveling in the company of an unmarried woman half his age. Jack promptly married Flora and this charge was dropped. However, he was immediately rearrested on a Ohio warrant charging him with having stiffed a group of musicians who had played at a road house he operated in Kentucky. This was followed with another arrest warrant charging him with grand larceny; i.e., the theft of the Lincoln towncar, as by this time the dealer's effort to present the promissory note to Ed Ryan was rebuffed with the statement that Ed owed Jack nothing.

Jack was returned to Cincinnati in chains and arraigned for the alleged crimes. Strangely, almost two years passed before the grand larceny case was called for trial. During this time, Ed had died, and Ryan offered the defense that the State had failed to establish the fact that the auto dealer's agent had actually presented the note to Ed directly and that Ed had personally refused to pay. Ryan produced a witness who testified he was the manager of a real estate office in St. Louis, where Ed had a desk, and that the dealer's agent had come in to the office at at time when Ed was not present, tendered the note to the manager who told the agent he did not have authority to accept the note on Ed's behalf. The consequence of this evidence was that the trial judge instructed the jury to find Ryan not guilty, and Ryan for at least the third time in his life, walked. There is no record of what happened with the check kiting charge but it is probable it was dropped when Ryan paid the musicians off.

1925 Lincoln Town Car

El Paso Times, Sept. 1925

Cincinnati Enquirer, September 1925

According to the newspaper accounts this charge was
still pending when Ryan won acquittal on the grand larceny charge,
and there is no court or newspaper record explaining what
happened with the insufficient fund charge. Given the fact the
the evidence shows Ryan in California as early as June 1928,
it seems likely the charge was dismissed.

Jury Verdict on Grand Larceny Charge

St. Louis Post-Dispatch, July 22, 1927

Cincinnati Enquirer, July 1927

Cincinnati Enquirer, July 21, 1927

In 1926-27, Ryan lived in Covington, KY, with Flora

In the summer of 1928, Jack Ryan surfaced in Los Angeles, California when an automobile he was riding in, with John W. Considine, collided with a vehicle driven by a man named Dicks. Dicks caused charges to be brought to trial against Considine, alleging he was the man behind the wheel, drove recklessly by swerving in front of Dick's car and then slowing down, causing the two vechiles to collide. At trial, Jack testified he was the driver and because—to the trial judge's eyes—Jack and John, two round-faced Irishmen, looked so alike the judge instructed the jury to find Considine not guilty, though Considine had hair and Ryan was bald.

Los Angeles Times

The two men had been friends now, for over twenty years, first coming together as partners in the Sullivan-Considine Theaterical Circuit, and cooperating, from time to time, in various gambling operations which Jack managed and Considine underwrote. Now Considine was retired from the theater business, having sold it to Alexander Pantages. He still owned a string of horses which he kept on a property in Potrero, California. The property was located in the Cayamaya Mountains about thirty miles east of San Diego and within two miles of the Mexican border town of Tecate. A railroad ran between Tecate and Tia Juana, which he used to move his horses back and forth between Sunny Jim Coffroth's race track at Tia Juana and Potrero. Whatever the reason for doing it, Jack lived on the property with Flora until he died of conjestive heart failure, in October 1930. Whether Jack owned the fee for this property, or some part of it, or none of it, is not known. Considine died in 1943.

Considine's Winners During December 1928 to March 1929

San Diego Union-Tribune, Oct. 1930

Cincinnati Enquirer, Oct. 18, 1930

Jack's Death Certificate

Cincinnati Enquirer

Los Angeles Times, February 1943

Potrero, CA. Jack lived on a property near the google mark

The Ruins of Jack's Last Home

Book of Ohio, 1910

St. Louis Post-Dispatch, 1904, Ryan Dressed in Cash


Joe Ryan