soldier with rifle american civil warJohn J.
"Bald Jack" Ryan©



John J. "Bald Jack" Ryan

Original Text By Joe Ryan

Part One

Jack Ryan's story is heavily documented in the newspapers of his time, because a very short-lived scheme he invented, in 1903, brought his name into print all across America, from Los Angeles to New York and all points in between. The consequence of this, is that everything he did thereafter, down to his arrest in El. Paso, in 1925, on the charge of grand larceny, and the charge's dismissal, in 1927, is recorded in the press. What follows is the record of his life.

Jack's Parent's, Born in Ireland, Come to America

John J. Ryan was born in Cincinnati, Ohio, on August 9, sometime between 1862 and 1866. There is uncertaintyas to the year, because Jack gave different dates to different people at different times. His parents, Michael Ryan and Helen Considine, were both born in Ireland. Michael probably was born in County Limerick, Helen in County Claire next door.

U.S. Census records show that Michael, born in 1836, came to America about 1855 and surfaced in Cincinnati, Ohio. He probably was a soldier in the Union army during the Civil War.  In 1870, he was employed as a coffin maker, and by the 1890s was the "Keeper of the Morgue," a position that required him to go into the streets of the city with a wagon and remove dead bodies from the tenements and prepare them for burial. Late in his life, he lost the position when the City's contract with his employer, John B. Habig & Son, ended; by then, the city had built a new morgue and the politicians gave the job to someone else. He continued in Habig's employ until 1889 when he quit at the age of 85.

Cincinnati's railroad slot today

mike image

Mike Ryan


Mike's grand son and great grand son

The fact that, at the time of his death, Michael was living in a tenement on Barr Street, next to the city's railroad slot, suggests the unlikelihood he would be remembered by the reporters of the Cincinnati Enquirer as worthy of an obituary, unless they were induced to provide the recognition, by Jack slipping some bills into their hands.

Helen Considine was born in County Claire, Ireland about 1842 and appears to have arrived at New York with her parents, Patrick and Catherine Considine, around 1850. Patrick and Catherine had six children, three boys and three girls. Of the three boys, Michael Considine was the oldest; born in Ireland about 1843, he died in Cincinnati in 1905. Next in age was John Considine: born in Ireland no record is found of his death. James P. Considine was born in New York, in 1856, and died in Cincinnati, in 1890. Except for Mary Ann Considine, Helen's youngest sister, there are no photographs found of any of the Considines.


Jack's Considine Connections

Several Considines appear in Jack's life as close business associates, if not real friends. Whether any of them were related to Jack through his mother, Helen, the record does not show. But, given the fact the Considine clan came primarily from County Claire and, like all Irish Catholics of the day, were prone to have many children, the probability that some degree of relation existed between them cannot be negated.

George F. Considine and his brother, John R. Considine, clearly included Jack in their circle during their heyday as New York sportsmen at the turn of the century.

John and George, along with their younger brother, "Billy", spent their early days in Detroit. According to the archives of the Detroit Free Press, John "Johnnie" Considine arrived in Detroit as an ex-convict, in the early 1880s, after having worked as a roustabout with a traveling circus. Between the time of his arrival and about 1886, John Considine was considered a violent crook.




Though John Considine was charged with two murders, both charges were dropped as the killer in each case was ultimately identified as someone else. In March 1982, he got in a gunfight in a saloon and was shot in the chest.

Whether this experience sobered John up, it appears soon after his wounding he opened a saloon at 20 Monroe Avenue in Detroit, and operated it until he left Detroit for New York in about 1895. Given his quick emergence in New York as a successful businessman the assumption fairly can be made that he arrived in New York with a substantial amount of cash in his pocket—cash no doubt accumulated because of the gambling and other games that went on in the back rooms of the saloon.

Less than five years after arriving in New York, John became the owner and operator of a restaurant on the grounds of Dreamland, an amusement park on Coney Island.

Dreamland 1910

John Considine's Obituary in

The Detroit Free Press, 1909

Like John, George left Detroit in the early 1890s. He eventually surfaced in New York as a promoter of heavyweight fights and a "stakeholder" of purses in several championship fights involving James "Gentleman Jim" Corbett, among others.

By 1904, he and John were operating the Metropole Hotel and Café: first at Broadway & 42th Street; and then, in 1908 when their lease was lost, at 147 W. 43th Street.



The “Old” Metropole Hotel circa 1900

The “Old” Metropole” circa 1909

The New York Times, Aug. 1909

The Considine’s Broadway 1900-1920

The New York Times, Sept 1910

The “New” Metropole Hotel's Location between 1908 & 1912

The New York Tribune, 1910

The New York Times, 1912

The “New” Metropole circa about 1914

(Then operated as Rosoff’s Hotel)

In the summer of 1912, New York police detective Becker caused a gambler named Rosenthal to be gunned down on the sidewalk in front of the latter location, which ruined the Metropole's business, and George—John had died in 1909—closed the place. He filed for bankruptcy protection later that year, listing $5,000 in assets against $500 in debts. George died in 1916.



When John R. left Detroit, he left his brother William H. "Billy" Considine the operation of the Monroe Street saloon. Billy did so until 1908 when for some unexplained reason it passed from his hands. It appears Billy became unwelcome in Detroit and he left the city in 1911 and followed his brothers to New York. By this time John R had died, and George had divested himself from the operation of the old Metropole Hotel. In 1910, George built the building at 147 W. 43rd St that today is the Casablanca Hotel.

The record suggests that John and George, probably with Big Tim Sullivan’s involvement, and, perhaps, Ryan’s, controlled the lease of the lot upon which the old Metropole sat. This lease may have been sold, or it may have been renegotiated with the landowner, the Coe Family Trust, with the Considine’s, perhaps with Ryan involved, retaining a right to lease part of the ground floor of a new building to be constructed on the lot in 1910 by “Missouri” investors. As the consequence, a bar room was opened in the new building─known as the Heidelberg Tower─in 1912 called “Billy Considine’s bar, which remained in highly successful operation until January 1920 when as the result of Prohibition it shut down.

The Heidelberg Building Circa 1914

Detroit Free Press, 1904

Detroit Free Press, Aug. 1908

Detroit Free Press, 1908

August 1909 

Detroit Free Press, 1911

Billy Considine's New York Bar, 1913

Billy Considine circa 1913

Left to Right: Billy, Francis Considine, George’s daughter, Billy’s wife,

And Rosebud Agee

Billy’s House in New Rochelle, Long Island Sound Behind

The Babe, with family, sitting on Billy’s porch.

(This is like Pete Rose sitting on Nick the Greek’s porch.)

The New York times, 1915

In 1915, the Babe was a pitcher with The Boston Red Socks

but appeared only once in the World Series that year which the Socks won.

The Bookies


The New York Times, July 1921



The New York Times,1909

The New York Sun, 1912

The New York Sun, 1912


The New York Times, 1916

Big Tim and His Pals Partying

The New York Times, 1932


John W. Considine

About 1906, if not earlier, Jack developed a life-long friendship with John W. Considine, who, beginning about 1897, had established himself in Seattle, WA, as the operator of a string of notorious "box-Houses." Considine's mother and father, John C. Considine and Mary Cusick, both born in County Claire, came to America in 1854 and settled in Chicago. John C., it should be no surprise, made his living as a saloon keeper. From the marriage came Thomas Considine and John W. and six daughters. John W. reached Spokane, WA, traveling through the West as an actor, sometime in the early 1890s, and opened his first "box house;" essentially a bordello in the beginning and then, as his business acumen matured, a full-fledged entertainment establishment. His older brother, Tom, followed him, and the two moved on to Seattle. Full success came with the huge influx of men coming and going through Seattle, from the Alaska gold fields.

The flag ship of Considine's operation was the People's Theater, located in the basement of a downtown Seattle office building. The name mimics Miner's People's Theater that existed at this time on the Bowery, in New York City. Going down a set of stairs, you entered a large room filled with tables and chairs, with a bar along the wall, and a stage for vaudeville performances at the other end. A U-shaped balcony with cubicles hung above. Considine drew in the masses of workingmen with entertainment and made his money peddling liquor, prostitutes, and gambling; the profits gained he put into real estate and a string of thoroughbred race horses.

In early 1906, Considine became connected with Big Tim Sullivan, who had developed an entertainment empire based in New York City. The two men formed what was known as the Sullivan-Considine Vaudeville Circuit. With most of the vaudeville entertainers operating out of New York, Sullivan controlled their show dates at eastern theaters while Considine controlled their appearances in the West. Both men held an interest in a string of theaters Jack Ryan operated in midwest cities. As vaudeville died, and nickelodeons and then motion pictures became available, Considine, with Sullivan as his partner, built and operated vaudeville/movie theaters in every city on the West Coast. They opened the Lyceum in San Francisco and the Grand in Tacoma. By 1914, they had 21 theaters in operation in the West. During this time, Considine formed the Northwest Orpheum circuit which extended from Seattle to Minneapolis. In 1914, when Sullivan died, Considine was forced to downsize, selling off most of his theater holdings, in 1915, to Alexander Pantages. What he controlled in the East went to Marcus Lowe.

At the same time he was building movie theaters in West Coast cities, Alexander Pantages, once a penniless huckster, selling newspapers to the miners in Alaska, was developing his own entertainment empire. Pantages arrived in Seattle in 1902 and opened a theater. This brought the two men into feverish head-to-head competition—a competition that finally ended, in 1915, with Considine selling his theater business to Pantages; in the process, his son, John Jr., married Pantages's daughter, Carmen.

John W. Considine's Seattle "Box-House," 1900



The history of the times demonstrates that most American men, certainly the Irishmen featured here, carried pistols on their person, even in the cities. In June 1901, Considine shot and killed Seattle's ex-sheriff, one Meredith, who came into a barbershop Considine was in and fired a pistol at him.

Considine's brother, Tom, was present and he ran at Meredith as the revolver discharged, wrenched it from Meredith's hand and used it to strike Meredith several blows on his head. Considine, rising from the barber chair, pulled his own pistol and fired into Meredith's chest, killing him. Meredith came gunning for Considine because the two had been embroiled in a public war of words over an issue of Meredith accepting bribes from Considine's competitors to shut down Considine's saloons in which gambling was rampant. Considine had publicly threatened to sue Meredith for libel in the courts and Meredith's reaction was to find Considine and kill him. Considine was acquitted at trial in November 1901.

Seattle Times June 25, 1901

Los Angeles Times, June 26, 1901

Seattle, looking across the Line, 1900

Jack's Connection to Timothy D. "Big Tim" Sullivan

Another Irishman Jack Ryan formed an important connection with, was Timothy D. "Big Tim" Sullivan. Born in 1863, on New York City's Greenwich Street, Big Tim came up out of the Five Points District to be elected at the age of 23 to the New York State Assembly. Under the auspices of Tammany Hall chairman, Richard Croker, Sullivan had gained organizational control over the Fourth Ward, below Fourteenth Street, through an unequaled ability to bring out the vote in overwhelming numbers for the Tammany machine.


The center of the city's Irish community at the turn of the century, the Five Points District was known as the worst slum in America. As a teenager, Sullivan, working as a newsboy, roamed all over lower Manhattan, becoming familiar with every block and alley. He organized the newsboys as a semi-union, negotiating a contract for them with the five newspapers they served.  By his late teens, Big Tim had opened a saloon off the Bowery, and began building a political base to control the Fourth Ward. By his early twenties, he had ownership interests in six saloons which served as precincts for his political base.

George Bellows, Big Tim's Ward

In 1893, Sullivan was elected to the State Senate, representing 300,000 people crowded into the tenements bordering the mile-long Bowery. By 1900, he owned interests in restaurants, amusement parks, music halls, vaudeville theaters, burlesque houses, and a string of thoroughbreds. He also controlled the underworld of vice in New York City: prostitution and gambling. Big Tim gave Arnold Rothstein his start toward the big time, putting him to work as an accounting clerk in one of his gambling dens.

 At Albany, he pushed for legislation liberalizing restrictions on boxing and horse racing. Making money, he gave it back, by organizing picnics where vast amounts of food were served free to his constituents. Enough turkey, ham, potatoes, bread, beer, pie and coffee to serve as many as 5,000 hungry people, most of them single men from the lodging houses. Local vaudeville singers and musicians entertained the multitude as they ate. In 1903, now a United States Congressman, Sullivan began giving away thousands of shoes and wool socks every February to people who lined up in front of his three story club house on the Bowery, the line snaking down the long boulevard for blocks. He also was visible at the "Tombs," the city prison and in the corridors of the courthouse, ready to provide bail money to anyone from his district in need of it.

The Bowery 1900

Jack Ryan's Early Career

How and when exactly it was that Jack Ryan became connected with the Considines and Sullivan, the newspaper record does not say. What is known is that Jack arrived in St. Louis sometime in the early 1880s, probably drawn there by the tide of economic activity sweeping through it, to the West, which was raising it to its greatest height it would reach—the country's fourth largest city, knocking Cincinnati from that perch.



Jack once told the newspaper reporters a story of riding the rails in his twenties which has the ring of truth to it—given his subsequent bar room brawls and the gunfights he was in. Together with two hoboes, he told the reporters, he was beating his way back east from California, when he became stranded in Albuquerque. He was in the most straited circumstances of his life, he said. He and the hoboes jumped a freight train at the edge of town on the run, and found themselves in a box car with a brakeman holding an iron bar in his hands. In the struggle that ensued, Jack tore the bar from the man's hands, and cold-cocked him with it. At Oklahoma Station, with the man lying unconscious, perhaps dead, on the boards, Jack left the train and went directly into the labor contracting business; rounding up stray Irishmen from the saloons and gambling dives, he got them work laying sections of the Frisco extension from Red Fork to Sapulpa.

The Missouri Pacific & A.T.& S.F Extending their lines 

Labor contracting for the railroads was a big business in the 1880s, so it is reasonable to suppose that Jack made some money at it. Indeed, the railroads were a gold mine for a slew of characters of the times who got far richer from their connection with it than Jack did.

How Some Poor Irish Boys Made Good

Take James B. "Diamond Jim" Brady, for example. In 1880, there were 93,000 miles of railroad in the United States. In 1890, there were 163,000. In a single decade American enterprise had build as many miles of new road as had been built by the three leading countries of Europe since 1840. Diamond Jim started out selling handsaws for cutting rails, then dollies for cars, and, finally, steel railway cars. Brady made a good-sized fortune in the process. His business philosophy is good advice to any one, then or now, starting out to make a buck.


"Get to know the important men in every line. Find out which ones are doing the buying and if you can, find out which ones will be doing the buying in the next years. Make them your friends, make them understand you are the man who will serve them in the years to come. Make them trust you, and most important of all, make them like you."


Brady made his fortune, because, as he traveled up and down the country selling, he made friends with master mechanics, section foremen, road gang supervisors, station masters, train crews, roundhouse workers: no matter how great or how small they were, he made them his friends, learning from them how their work was going, what was coming next and what they would need.

In his traveling, whenever he got the chance, he found a pawnshop, went in and bought diamonds. Then he used the diamonds as props to set him apart from his competitors, using them in conversation to leave an impression with the clients and potential clients he met. He would pull out his wallet and fill his hand with diamonds and show them, tell the skeptical what the caret was, talk about the "points" and color, comparing them to others. If there was persistent disbelief, he would go to the client's office window and use a stone to scratch his name across the pane. Like a permanent billboard advertisement the etching would be seen by the passersby on the street and the client's business friends coming and going and the talk of him would continue long after he was gone.

Taking his profits, Brady bought race horses and a farm in New Jersey, and he gambled, at cards, dice, stocks, and the horses. It was all the same to him. By 1903, Jim was in control of the Standard Steel Car Company and his personal worth was twelve million.

One of Brady's cronies was John W. "Bet a Million" Gates, who, like him, had begun as a traveling salesman and ended up in the 1900s worth millions which he used, among other things, to gamble on the cards, stocks, and the horses. Born on an Iowa farm, Gates as a young man operated a hardware store in a place called Turner's Junction. In 1873, he came by chance upon a man named Isaac Ellwood. Ellwood controlled a patent on a new method of manufacturing barbed wire and had wrangled a license from the eastern manufacturers  to sell the rope west of the Mississippi. Gates, seeing opportunity, went to work for Ellwood. He traveled extensively through the West making contacts and selling the wire, making a success of the selling business; and then abruptly quit.

In 1880, Gates went to St. Louis and set up a factory to make the same wire Ellwood was making, and doing it without a license. Then, dodging the lawsuits and injunctions Ellwood threw at him, Gates undercut Ellwood's price, and, gathering a combine together, he stole a huge chunk of Ellwood's business.

By 1883, Gates had put together a trust (a group of competitors fixing price and production) and gained control of the western market. First, he formed the Columbia Wire Company; then reorganized by buying out competitors and opening new plants. The reorganization resulted in the formation of the Consolidated Steel & Wire Co., which, in turn, as the years passed, became the American Steel & Wire Co., and this was finally folded into the United States Steel Corporation in 1901, when Andrew Carnegie sold his interest in steel. Gates died in the Hotel Meurice, in Paris, in 1911.

John Gates' St. Louis Residence in 1885 as it Existed in 2010

Jack Establishes Himself In St. Louis

The record shows Jack in St. Louis, opening a saloon in 1887 at the age of twenty-four. He meets and marries Anna O'Leary, one of the daughters of John J. O'Leary, a successful St. Louis ice and coal dealer.

In 1889, Jack leaves his saloon in the hands of his brother, Ed, and returns to Oklahoma Territory with his new wife, and they ride mules across the line early, and he stakes out lots which he sells to the caravans of late arrivers. Returning to St. Louis and his saloon, he gets close to Edward Butler, the King of the St. Louis boodlers. Butler had been a blacksmith who specialized in shoeing the horses of the street cars that clanged up and down almost every street in the city. Gaining an exclusive license to sell a patented horseshoe designed for street car horses, Butler had contracted with the city to shoe all the horses used by its agencies. To service the business, Butler opened up a string of farrier shops throughout the city wards and through them he became connected with the saloon-owners who operated as block captains, responsible for getting out the vote for the Democratic party in Election Day.

By the 1890s, Butler was the acknowledged boss of St. Louis politics; with the majority of the delegates to the city's Assembly loyal to him; every license to do business, every contract for services, every sale of property, every permit for a construction project—not to mention the many construction contracts the city was making for public buildings—passed through Butler's hands for a fee; the fees happily paid to Butler by the Social Register St. Louis businessmen, who controlled the banks, the street car companies, and the factories, in exchange for the city contracts, franchises, and other special privileges.

Jack Becomes a Horseman

In the early 1890s, Jack became a bookmaker and then a horseman. And this must explain how he came eventually to know George and John Considine and Big Tim Sullivan. The "sport" of horse racing in those days was smoke and mirrors: the lambs—the public masses who came to the tracks and bet—were fleeced of their money in a variety of ways. The "class" of the horses was one thing on the tout sheets the lambs read before laying down their bets, and another thing when they were lined up at the ribbon. Indeed, rarely could the betters be sure they knew the identity of the horses actually running in the race.

St. Louis Jockey Club and Race Track: 1900

The Lambs at the St. Louis Races

Jack learned bookmaking at the St. Louis tracks: he became a student of the schools of handicapping—class vs. time. He learned how to clock a horse, timing from the actual start, breaking fractions down to a hundredth second, recording the margins between horses, the wetness of the track, the consistency of the soil (thick gumbo vs thin soup), the wind velocity, and the placings of the also rans. Horses coming out of separate races on different days would meet later, and a horse with a winning mile of 1:40 against a head wind would get a bigger figure than a horse with a winning mile of 1:39 helped by a tail wind. He learned to walk the racing strip, studying it for soft spots, holes, and whatever might affect the figures. Handicapping could be upset over night by an order from the track manager to harrow the surface toward or away from the rail. Making the surface either deeper or firmer.

He absorbed the nuances of the game, betting round a weak favorite with two or three strong long shots. If there are only two speed horses in a race, take the one on the inside. He is bound to go to the front. The one on the outside will take back. It will slow down the pace and give the inside horse the chance to stick it out, pulling away when it is too late for the outside horse. If there are three or more speed horses, look for stretch runners. Of course, if there is only one speed horse, betting on him to break on top is elementary. Unless he's in over his head. If you find a speed horse that has been quitting in classy company and is dropping down among cheaper horses you've got a perfect spot. This horse should hold his speed now. Horses dropping down in distance are good bets, too, so long as they are not moving up in class.

And, of course, he learned how the gamesters manipulate all of this. Trainers leave a blank, "No boy," in the overnight entries, and the following morning they come with a GO boy, throwing off the newspaper handicappers who influence the odds with their selections. Drugging horses to run fast or slow, putting sponge in the nostrils of the horse, jolting the horse with a battery, rigging the horse in the barn to look sick, bribing the jockey to wear the horse out early, take him wide, or squeeze him into a pocket; or the trainer to make the horse weak or strong, or an assistant starter to hold a horse back, or give it a flying start.

Finally Jack had to learn the racket of bookmaking, the difference between a percentage book and a gambling book. In theory the bookmaker's role was supposed to be the middleman, a stakeholder: take enough on the beaten field to pay off on the winner and still have a profit. In practice it did not work this way: in a field of 10 horses the bookie would get 90% of his money on three or at the most, four horses; and just a few dollars here and there on the outsiders, making it impossible for him to keep on the right side of the ledger. So, unable to make a percentage book, he made a gambling book. He would hold out or reduce the odds against any horse he thought could win, at the same time raising the price against the others. For, example, if a lot of money was showing on an even money horse the bookie would get $500 from another bookie and then lay the same horse in his book at 4 to 5. If the horse won he was $100 ahead. If it lost he was even.

The Betting Ring

The first time Jack gained entry as a bookmaker to the betting ring, he would have been overwhelmed, for a few moments at least, by the apparent chaos of the place: the milling crowd of men pressing in against the stands waving money with their fists; cappers mixed in, gesturing a mark toward one bookie stand or another; paddock men coming in with updates on the horses moving to the post; the bookies keeping in line, chalking their slates, changing the numbers as reports come in what odds their neighbors are showing, what horses well known plungers are betting on; runners rushing in with reports such as "This horse is not trying," or there is a "knock on the favorite," or "the right money ain't showing." False rumors mixed with true.

The New York Stock Exchange, Just Another Betting Ring

Behind each stand—boards braced on stools enclose the space—there is a crew of clerks concentrating on their special tasks. The sheet writer writes down the bets as the bookie grabs the money from the lambs' hands, he tears off a page when the race is run and hands it to the cashier who pays the winners off at the back of the stand. The bettors are in line and, above the din, the cashier shouts, "What number?" "Thirty-eight," responds the bettor. The cashier comes back with, "What's the horse and the bet?" "Fifty dollars, Gold Heels to win," the bettor answers. The cashier scans the sheet, finds the entry, circles it with his pencil, opens the cash box and pays the man, gesturing for the next in line to step up. At the same time, more men are crowding up to the front of the stand, calling out their bets, giving up the money and taking numbered tickets in return. In the middle of the stand, sitting on a stool, the tab man holds the bookie's ledger in his hands, keeping track of the money coming in, the amount bet on each horse, the changing odds, the money going out, constantly calculating how much the book can stand to lose on a race. The key to all of this action, of course, is the crowd of men in attendance at the track, it's their putting down the money that makes the odds move.

Once Jack learned how to offer the bettors odds in a way that guaranteed the book would at least break even whichever horse won, he moved up to the level of managing the horses and orchestrating betting coups.

There are a thousand ways a horse can win or lose a race, and Jack plainly learned them all. In the process of shifting from bookmaker to horseman, he became adept at running horses below their class, keenly calculating the odds by studying the jockeys, weights and distances. As time passed, though, the evidence points to his developing more sophisticated methods of separating the lambs from their dollars.

Jack Sets Forth For The Big Time 

With a solid base of experience gained from the St. Louis track, Jack moved into Illinois. He established a saloon on Converse Street in East St. Louis, down by the river front; drawing in the workingmen from the railroad yards and meat packing plants; and then, leaving Ed to handle things, he forayed to Chicago's Hawthorne track, got in with the big boys and made some killings using St. Louis horses as "ringers." From Chicago—the owner of a string of thoroughbreds now—he went through Michigan and Ohio and, finally, toward the end of the Nineties, he reached New York and the tracks of the eastern seaboard.

Converse St. East St. Louis 1895

Converse Street Gone, 2014

In the years of his education, developing his profession, only once did Jack get caught by a Jockey Club "ringing" a horse. In September of 1898 at a small time track on the Canadian side of Lake Erie, the stewards became suspicious when a horse named Caroline K won a race in which she was running far above her class. The stewards went to the barns looking for the horse and were surprised to see the jockey booting her out the gate and galloping off down a country road. When the jockey and horse were found, the horse was exposed as not the Caroline K listed in the stud book and Jack's name was dropped as the owner. Using the benefit of borders—a tactic he developed to an art—Jack escaped the Canadian authorities and the matter was dropped, though the charge came back to knock him when he was on the mountain top, in 1903.

From The Daily Racing Form (1896))

Faking and manipulating the health of the favorite horse became Jack's specialty, though in those wonderful days of raw gambling it was no more improper to conceal the form of a horse than to conceal the strength of a poker hand. There were always spies (touts, stable hands etc) swarming the barns where the horses were kept, looking for signs that a horse had been "hyped" to win, or was sick in some way, or whether some other means of fix was in. Sometimes Jack would let them see one of his people sticking the needle in and, not knowing only clear water went into the vein, they reported the event to the lambs and the money went down as the odds on the other horses went up. Ryan would have his money down on another horse he expected to win. Other times, he would leave a water bucket with a sponge soaked in chicken blood in plain view. The touts would report it to the betting ring and the odds against the animal winning would go up and Ryan would make a killing. Here's an example of Jack's work, as reported by the Washington Post, referring to an episode in 1898.

It is reasonably clear that, around 1895, Jack Ryan met up with George Considine, and his brother John, in New York, where by then they were successful gamblers, promoters of prize fights, and owners of entertainment establishments, saloons, restaurants and hotels, and that through the Considines he was introduced to Big Tim Sullivan, King of the Bowery and the great Irish politician of the day.

Between 1896 and 1900, Jack became a major actor in Sullivan's gambling syndicate. Sullivan and the Considines owned strings of horses and Jack was the manager. These horses, as well as his, were raced at Sheepshead Bay, Brighton Beach, and Graveshead in August and September, then taken south to the Maryland tracks. It appears that Sullivan's syndicate, using Jack as its front, or Jack himself—the record is not clear—bought a horse farm at a courthouse auction in Elkton. The farm was located nearby Elkton in what is known as Town Point, Maryland. At the same time, Sullivan's crowd organized an "outlaw" race track known as the Iron Hill Race Track, at Elkton; and the syndicate's horses, as well as Jack's own string, were run at this track with much profit.

Racing Form News, 1896

By the 1890s, the scheduling of horserace  meeting were sanctioned by two dominant racing associations—one controlling the meetings west of the Alleghenies and another controlling the meetings east of the mountains. Under the auspices of these two associations, local "jockey clubs" provided oversight of racing events within their area through stewards who managed the races day-to-day. Stewards supervised the weighing of jockeys at the scale, the start and finish of the race, and they disciplined jockeys, trainers, and owners who they suspected  had engaged in manipulation of a race's outcome. The monopoly on race meetings that this set up provided the eastern and western racing associations was broken up by the emergence of "outlaw" race tracks operated by men like the Sullivan, the Considines, and Jack. The consequence was economic war between the outlaws and the mainstreamers. Any one—owner, trainer, jockey—who participated in outlaw racing was in danger of being black-balled from the official tracks.

Town Point Between the Elk and Bohemian Rivers

(The Iron Hill Race Track is at Elkton)


Sullivan and the Considines were The "Metropole Stable"

In addition to Jack racing his own horses,

He was  the "Melrose Stock Farm" 


"Helen Ryan" was the name of Jack's second child, born in 1897. 

The outlaws' operation of the Iron Hill race track lasted, it seems, about three years. By 1899, Jack and his pals moved their racing combine, first, to Wheeling, WV, and then to Carnegie, PA, a spot about ten miles outside Pittsburg. In all cases, their focus was on taking the dollars from the mass of workingmen attracted to the different localities by job opportunities, in the mines and steel mills, or in the factories of the cities—Iron Hill at Elkton, for example, being on the railroad line between Baltimore and Philadelphia, an hour's train ride.

Jack Reappears In St. Louis

In 1901 Jack came to St. Louis, it appears with the intention of developing an outlaw track to entertain the millions of lambs that would be attracted to the Worlds Fair the City was planning to host, in the summer of 1903. Ryan partnered in this endeavor with a local liquor distributor, Patrick Carmody. (Carmody had hoped to partner with John W. Gates and his sidekick, John Drake, but he got Ryan instead.) The two men chose a undeveloped parcel at the north end of Union Ave as the track's site, and began lobbying the politicians in the city Assembly to give them, not only a building permit and a license to operate the track but also a franchise to run a trolley car service from its existing terminus on Union Ave to the track. The vision of the money to be made from the millions of lambs flooding the city in search of thrills and entertainment must have been swimming deep in the currents of Jack's mind at this time.

In 1902, Ryan's and Carmody's efforts encountered difficulty when the St. Louis's graft system of politics threw its weight behind a group of St. Louis millionaires who were pushing the Assembly to give their street railroad company, The St. Louis & Suburban Street Railroad Co., an exclusive franchise to provide trolley service on St. Louis streets. Their leader, one Charles H. Turner, had gone to Ed. Butler and asked how much it would cost to get the ordinance granting the franchise passed. When Butler replied, "My fee will be $145,000," Turner and his group approached various assemblymen directly, offering bribes to those who promised to deliver a majority vote. Ryan and Carmody sought to compete in the bribery contest but the whole thing became impossible, when Circuit Attorney Joseph W. Folk started throwing indictments around which resulted in Turner and his crowd having to weather a felony trial. They lost it, but the Missouri Supreme Court, as it frequently did in those days, bailed them out by reversing the jury verdict on a technicality. Further complication was encountered when the city fathers decided to postpone the Fair, until the summer of 1904. In the graft environment of the day the Assembly had passed out a number of contracts to the millionaires and Butler's cronies to pave city streets, provide lighting, clean up the brown slity water that came out of the taps, and construct a new city hall and courthouse. All of these projects, mired in kickback schemes that were diverting materials and running in the red, had to be completed, if the city was to handle the masses expected to attend the Fair. Then, Circuit Attorney Folk indicted Ed Butler on a bribery charge involving a garbage contract which further disrupted the orderly transaction of business as it was practiced in the city, and the date of the Fair was pushed into 1904.

Jack rose to the challenge these complications presented, by deciding to take a page from Big Tim Sullivan's book of how the Tammany system of government worked. Perhaps with Tim's active encouragement, he developed a plan to become the "big fella" in St. Louis politics, with the goal of getting practical control over the Tenderloin District of St. Louis—the 4th and 5th Wards—and thus have two ways to get into the wallets of the lambs flocking to St. Louis for the World's Fair.

First, he partnered with John "Cuddy Mack" McGillicutty in the opening of a saloon in the Fifth Ward at Sixth St. and Franklin Ave. Next, he opened another saloon in cooperation with Carmody, in the adjacent Fourth Ward. These actions, of course, conflicted with the plans of men who had already established themselves in the pecking order of St. Louis politics—especially Thomas "Snake" Kinney, who saw himself  taking Butler's place at the top. Kinney, political leader of a gang of toughs called the Egan Rats which operated out of a saloon at Second and Carr in the Fourth Ward, eventually reacted to Ryan's challenge by throwing lead at him.

The Saloon at Sixth & Franklin

St. Louis's Stewart Place Today: Jack's family lived here in 1900 

St. Louis's Millionaires' Row: Portland Place, 1900

Jack Plunges into St. Louis Politics

Jack's struggle with the Kinney Gang for control of the Fourth Ward began with a struggle between stand-ins—the slate of delegates each side put up for election to represent the Ward in the City Assembly.

The conflict between Ryan and Kinney for control of the Fourth Ward ended with Jack escaping town with his life. Kinney let out all stops that year when he initiated a bombing campaign against Ryan's saloon and then sent the Egan thugs to kill him.

Thomas "Snake" Kinney was a major player in the Fourth Ward when Ryan appeared in St. Louis in 1900. By then, he was the recognized political leader of the Irish street gang known as "Egan's Rats." Kinney, and his brother, Mike, had grown up in a tract of land called "Kerry's Patch."  In the 1820s, the Patch had been a forested tract of land on the City's near north side, owned by a millionaire Irishman named Mullanphy. But, in the 1840s, when the waves of immigrant Irish crashed into St. Louis, they came to rest on the tract with Mullanphy's blessings; by the 1860s, the track was a vast shanty town; by 1900, a grid of cobbled streets with blocks of  three-story brick flats teeming with second generation Irish.

Heart of the Patch Today

Jack's nephew, "Little Joe" lived here between 1916 & 1920, attending St.Leo's School 

Little Joe's 1916 grades at St. Leo's

With the support of Carmody, Ryan was named a prospective delegate to represent the Western District of the Fourth Ward in the city legislature, while Kinney was named a delegate to represent the Eastern District.

In the course of the general voting that followed, a riot occurred in Ryan's district, when a crowd of African-American men were refused admission to the saloon serving as polling place. The angry Africans milling outside, became aware that Ryan, acting as polling judge inside the saloon, was stuffing the ballot box with heelers coming in through a back door, and someone drew a revolver and a shot rang out.

Immediately the saloon became the scene of a fusillade. Every man came out with a pistol and ran into the street, and, among them, came Ryan who shot squarely at an African advancing upon him with a pistol in his hand. Ten policemen were on the spot in minutes and succeeded in dispersing the crowd of Africans. But, in the confusion and alarm, someone slipped in the back door of the saloon and stole the ballot box.

Ryan pressed into service a cigar box and stuffed it with reconstituted ballots. Then, slinging a Winchester rifle over his shoulder, he carried the cigar box to the Election Commissioner's office in the company of his supporters. While the Commissioners were questioning Ryan about the provenance of the ballots, Snake Kinney arrived with the ballot box of the Eastern District, but Ryan's crowd loudly objected to its receipt on the ground the returns were not signed by the polling judges. In the heated arguments that followed—Ryan and Kinney waving guns at each other—the Commissioners decided to let the Convention resolve the muddle when it convened the following day. When the issue came up for the Convention's vote, Kinney induced a Convention member controlling a block of votes ostensibly Ryan's, to switch them to a Western District man named Sheridan and Ryan found himself out and Kinney in.

Now Ryan turned his attention to the Fifth Ward, then in the control of  Snake's brother, Mike, and a terrible fight began for supremacy between Ryan and the Kinneys for control of the action on the entire North Side. (Snake Kinney would represent  the old Patch section of St. Louis in the Missouri State Senate a few years later, and his brother, Mike, taking his place in 1912, would hold the seat to 1968, when, finally, at the age of 90, he was defeated by an African-American.)


It was then, within a month of the voting fiasco in the Fourth Ward, that Ryan, with the help of Cuddy Mack, opened the saloon at Sixth St. and Franklin Ave, a street intersection in the heart of the Fifth Ward that now sits inside the National Football League stadium the City's taxpayers built in 1995. And this is when the bullets really began to fly.

Franklin Ave, 1900

The saloon had the corner space on the ground floor of  the Holland House, a four story stone and brick affair with awnings over the upper floor windows. Garish painted street cars, clanging and sparking, run up and down the Avenue in congested packs all hours of the day and late into the night. Black shiny carriages clatter on the cobblestones between the cars and the curbs, and come to brief stops in front of the tight-packed buildings that stretch up-town from the corner, the building facades covered with countless signs of the commercial concerns that rent them. Yellow lights glow in the windows of  the shops at evening, and a pall of heavy smoke from the black factories and steel mills along the waterfront, backed up by wretched tenements and Tenderloin dives, perpetually hangs low over the canyon of the street. In the alleys in back, trade carriages of innumerable types constantly come and go, delivering and removing parcels, liquor, waste and the like. On the sidewalks, sharp-faced fellows wearing curly-brimmed low crowned derbies, tight black suits with short jackets and vests and low stiff white collars, walking in twos and threes, congregate at the corners, wait for a break in the traffic, and continue toward their destinations.

All of this is the normal routine of the Avenue, until two men and two women in a buggy drive past Ryan's saloon on a Saturday night and fire twice into the place, shattering the large plate glass window in the front. The police arrest the people in the buggy and find a pistol and cartridges in the possession of a passenger, one Frank McGorey, but everyone denies knowledge of the shooting and since every adult male in St. Louis at this time possesses an open carry the police can't prove a thing. The bombardment is repeated half a dozen times in the month that follows, but Ryan and Cuddy Mack replace the glass and go on about their business, which is to draw the solid Irish huskies of the Ward to their side and muscle out Kinney's men from the music halls, gambling dives and brothels.

Then one night a known henchman of Kinney walks in: Red Houlihan, a dark-eyed, beefy, thick-necked man with a bashed in nose. The place is packed with tough St. Louis wise guys, and Houlihan puts his thick arms in front of him like a wedge and pushes his way through the throng to Ryan, who is standing at the bar watching him come in the huge wall mirror that overhangs the back of the bar. Cocking his big right fist, Houlihan grips Ryan by the shoulder as Ryan—a big physical man in his own right—spins and drives a highball glass straight into Houlihan's face. The glass shatters from the force of the blow and shards cut open Houlihan's cheek to the bone, the laceration extending to the eye. Momentarily surprised, Houlihan staggers back a step and Ryan slugs him to the floor with quick rights and lefts, but Houlihan rolls away, gets to his feet, and grapples Ryan in a bear hug, and, with a great grunt, drives him back hard against the edge of the bar.

Here the two furious Irishmen strain against each other, banging heads, kneeing each other's groin; until Ryan slips and twists along the bar, breaks Houlihan's hold on him, and swings a vicious roundhouse right against the side of Houlihan's head that connects with the sound of a mallet, bringing a roar from the excited men thronging round them. Houlihan staggers. Quivering and snorting, the laceration on his face streaming blood, he tries his battering ram trick again; this time down chopping with his left, following with a right hook that catches Ryan flat on his feet, and now Ryan goes down and Houlihan is stomping him and Ryan is rolling. Up again, Ryan clinches with Houlihan. Everybody in the room is shaking fists in the air now and shouting cries of "punch him, Jack! Punch him!" "Get the bastard!"

In the midst of the shouts, Houlihan pulls out a pistol and the two men stumble and stagger in a spinning embrace, with the crowd opening way, across the bar room floor to the edge of the basement stairs and down they tumble into the darkness and land in a crash on the subterranean floor. With a great shout of "OHHHH!"—the spectators surge to the banister that encircles the staircase and the men in front grapple with their neighbors for a place at the rail. Sounds of grunts and shuffling feet, of storage racks and stacks of beer cases toppling and bottles shattering rise from the shaft. And then suddenly—the echoing balooom of a pistol shot explodes in the darkness at the bottom of the stairs and the men crowded against the banisters see the muzzle flash.

Silence strikes the men as they freeze where they stand and strain to listen, all eyes drawn to the well of darkness at the bottom of the stairs. A long moment passes. Everything is hushed silence. Then they hear the heavy scraping of a foot and Red Houlihan comes into view. He looks up at the silent crowd with an expression of bewilderment on his bloody face, his hands clutching at his stomach, and begins to climb the steps, then falters and finally falls backwards to the floor as Ryan steps out of the darkness, steps over Houlihan's dead body, and climbs the stairs with Houlihan's pistol in his hand.

Twelfth and Clark Today

Two weeks later—the Coroner's Inquest having determined Houlihan's shooting justifiable—Ryan is standing on the northeast corner of Clark and 12th Streets., opposite the central police station. It is ten o'clock in the evening and he is waiting for a friend, State Senator John P. Collins, to join him, when he sees, not twenty feet from him, three men, Mike Kinney among them, with guns in their hands, crouched against the building wall on the south side of Clark Ave. Ryan reaches for his pistol but before he can bring it out, Kinney fires two shots at him. The first bullet misses, but the second penetrates the left side of his abdomen, barely missing his liver, and passes out above his right hip. The shooters turn and run down Clark Ave to an alley and Ryan staggers after them, firing his revolver. He sees Kinney duck into the rear entrance of Kochler's saloon, but before he can gather himself to follow Kinney into the place a policeman runs up, hears Ryan's story in a breath and goes in himself, arresting Kinney inside.

Within five minutes of the shooting, with Ryan lying on the sidewalk at the entrance to the alley, a fellow named "Bad Jack" Williams, a former police officer, Ed. Butler's personal liaison with the ward gangs, and a score of Ryan's cronies, arrive at the scene and carry him two blocks to the city hospital on 14th Street. From his hospital bed, Ryan identifies the other two men as Mike's brother, Snake, and one Sam Young, a capo for the Egan Brothers' gang. All three men Ryan fingered admit being present in Kochler's saloon when the policeman rushed in, but all deny being out on the street at the time Ryan's shot, and a crowd of men in the saloon at the time back their story up, resulting in District Attorney Joseph Folk dropping the charges brought against the Kinney brothers.

Not too long after, one of Kinney's thugs steps onto a Franklin Ave street car late one night, comes out with a pistol and starts shooting at Cuddy Mack who's standing at the back. Cuddy Mack returns the fire and in the exchange one of his bullets stricks and kills an innocent bystander. Cuddy Mack's charged with murder and tried for the crime, but the jury acquits on the ground of self-defense. In 1902, he gets elected as constable for the  Justice of the Peace of  the Fifth Ward.

It's now that Jack reorganizes his game into what will be his greatest scheme, winning him national fame as John J. "Get Rich Quick" Ryan.

In the winter of 1901, an unemployed thirty-one year old New York newspaperman named Jacob Herzig caught Jack's attention. For several months Jack had been seeing the spread of  tipsters' advertisements—all claiming they were continually giving the public winners on the races—in the newspapers. Among these appeared a superior, more polished form, the copy written by Herzig. Given a tip by a friend, who had New Orleans race track connections, that the wise guys had their money down on a horse named Silver Coin to win, Herzig decided to get into the tout business. Adopting the name Maxim & Gay as an business alias for his tipping bureau, Herzig rented an office on Broadway and went around to the New York Morning Telegraph and paid for the insertion of this ad.

Bet Your Last Dollar On



At New Orleans

He Will Win at 10 to 1

In a postscript to the ad, Herzig informed the reader that though this tip was free, the next would cost $5.00, the tip to be received at the Broadway office of Maxim & Gay the following day.

Bringing in his friend, Herzig got his hands on the wise guys' horse for the next day, a pig named Annie Lauretta. Then, having typed the horse's name on a thousand slips of paper, putting the slips in envelopes, he opened the door of his office for business.            Outside, a line of men and women stretched down the hall, down a flight of stairs and into the street. For two hours, to within fifteen minutes of the calling of the race, Herzig was handing out envelopes and getting five dollars in return. Giving up the last envelope, he hurried out onto Broadway and ran for the Metropole's bar where there was a news ticker in operation. The horse won big—coming in at 40 to 1 odds.

Now Herzig got a better office and inserted a flaring full page advertisement announcing that Maxim & Gay had given Annie Lauretta at 40 to 1, and, previously, Silver Coin, at 10 to 1, and were ready for more business. Money was wired to the New Orleans contact to spread around with the trainers, clockers and every other source he could reach, for the very best information. Soon, Herzig had agents at the big tracks, selling the tips in envelopes at $5 each.

Herzig's success was phenomenal. Between 1901 and 1903, he claims he grossed in excess of $1.5 million. There were some weeks when the business netted over $20,000 profits. At the height of its career, in the summer of 1902, at the Saratoga race meeting, its net profit was $50,000. To Jack's eyes, the power of aggressive advertising Herzig had demonstrated, was exactly what he had been looking for to spring a scheme he had been finessing since Iron Hill which lacked the flaws in Herzig's model.

So flushed with success was Herzig that, in 1901, under the nom de plume, Maxim & Gay, he had filed suit in the New York courts against several persons who were reselling his tips at a lower price. The judges laughed him out of court.

A court of equity is asked to lend the aid of its great writ of injunction to preserve to plaintiff its business of selling tips to gamblers on horse races. The Constitution of the State provides: `Nor shall any lottery or the sale of lottery tickets, pool selling, bookmaking, or any other kind of gambling hereafter be allowed within this State.' The tips and advertisements of plaintiff are devised and intended as an aid to and an incitement of this forbidden gambling and betting, and such aids and inducements may be availed of as well in poolrooms as on race tracks. This court will not lend its equitable process in aid of plaintiff in its efforts to promote and induce acts forbidden by the Constitution. Petition Denied: Plaintiff to pay ten dollars cost.


The obvious flaws in Herzig's scheme were, first, he was giving the lambs the tip, and, second, his scheme was against the law.

End Of Part I

Part II