soldier with rifle american civil warTHE HORSEMAN©
John J. Ryan


John J. "Bald Jack" Ryan

Original Text By Joe Ryan


Part Five

Jack Returns to Cincinnati a Capitalist

It's interesting how Jack's public persona so easily changed from one time to the next, the newspaper reporters who covered him one year forgetting what he had been the next. Here, in his paid-for-blurb, Jack erases his history in a sentence, replacing it with credentials he manufactured. For there is no record of his attendance at St. Joseph's College, a small Jesuit school that existed in Bardstown, Kentucky, in the 1870s; nor can Cincinnati's Xavier University of today find any evidence he attended there, when it was a small Jesuit college. Then, in a breath, he leaps his history from a position as a clerk at the Reed's Hotel to unspecified positions in the "banking and brokerage business." How easy it is; twenty years of hard scrabble life gone in a line of words written on a page.

In October 1903, Jack came back to his family in Cincinnati, and the Windsor Street residence he had purchased at the time his father, Michael had died, in March 1903. It was certainly no mansion, on the scale of the St. Louis Millionaires and their Portland Place, but, for Cincinnati, it was about as plush a place as you could get.

1172 Windsor St., Cincinnati today

(Jack's family lived here until about 1909)

Upon his return to Cincinnati, Jack's first step was to cut loose from the grip of the Federal Government which had hold of him as a witness in the trial of Daniel Miller and Joseph Johns; the two men he had fingered as conspirators in a scheme to bribe him, in exchange for the Postal Department allowing him to continue to use the mails in his turf investment business. Having been granted immunity from federal prosecution for his alleged fraudulent use of the mails, he appeared as a witness against the two men in two trials; the first ending in a hung jury, the second in acquittal.

Daniel Miller was an assistant to James Tyner, who in turn was assistant attorney general to the U.S. Postal Department. Joseph Johns was an Indiana attorney who Ryan said he had met in a hotel room in Fort Wayne, during the time his turf investment business was being investigated for mail fraud, in 1902. Ryan said Johns told him he had a friend in Miller who would orchestrate a clearance for Ryan in exchange for $5,000 at which point Ryan gave Miller $2,500. In fact, George Christency, acting in place of Tyner who at the time was ill, signed off on the clearance letter Ryan received in December 1902. apparently this was done on the ground that, since A.J. Arnold had already been given a clearance letter, Christency could see no good reason not to give Ryan one.

Finally, the jury in the second trial got to the truth of it, by finding Jack had given Johns the $2,500 as a fee to secure Johns's representation on his behalf during the investigation; and Johns, along with other lawyers Ryan had hired, simply appeared with him in Washington as his counsel when he was interviewed by Christency.

Of course, if there was not actual chicanery, there was at least some gross negligence at work in the Postal Department at this time. Like Miller, Christiancy, and others, Tyner was also discharged from office and charged with felony breach of federal statutes, but the trial of the charges, as with those against Miller and Johns, resulted in acquittal. Only Kansas Senator Burton was convicted as charged. And then only after a trip to the United States Supreme Court.

Kentucky Citizen, Oct. 14, 1903

With Jack's trials seemingly behind him now, this was the time to truly leave his past behind, reinvent himself as a high class citizen, joining the ranks of Cincinnati's social and business elite, whoever they were, and, making use of the substantial amount of capital he now commanded, achieve for himself and his family, financial stability and security. Perhaps, with his Irish charm, run for political office, for mayor of the city let's say.

One obvious method of doing this, was to invest in real estate, in the fashion of the Donald Sterlings and Donald Trumps of our day, and Jack did, indeed, plunge into it. In 1904, he paid $70,000 for a 24 unit apartment building at the corner of Park Ave and McMillian St, and purchased several flats, bought a couple of lots and began construction of rental units. At the same time, though, its obvious he just couldn't let go of the gambling game. Here, it must be said, that Jack knew a great many men who made a good living in the gambling game, chief among these men was Big Tim Sullivan, and in the coming years Jack and Sullivan repeatedly mutually invested in business affairs.

This building was gutted in the early nineties and the interior renovated.

(It produces twenty grand in monthly revenue)

Cincinnati Enquirer, Jan 1904

Ryan's Gilbert Ave Flat

(The price is overstated)

Cincinnati Enquirer, Jan 1904

Cincinnati Enquirer, Jan 1904

St. Louis Post-Dispatch Feb. 3, 1904

Chicago Tribune, Feb. 26, 1904

Cincinnati Enquirer, March 8, 1904

St. Louis Republic, April 1, 1904

(Jack's way of making up for the fight)

Washington Post, April 10, 1904

(The Post followed Jack over the years)

So you can see Jack was having a rosy time, the best of both worlds—the world and the underworld, I mean—when he headed east again the summer of 1904, to reprise his great time at Saratoga with his pals the Considines. But no sooner had he arrived in New York, than a police detective showed up in his face and slapped handcuffs on his wrists.

Back in St. Louis, intoxicated with his popularity among the masses, old Holy Joe Folk had announced his candidacy for governor of Missouri, and, not wanting to live through the embarrassment of seeing Ryan headlined in the St. Louis papers, throwing money around the Saratoga betting ring again, he caused a new indictment to issue from the Grand Jury against him. This one was based on the complaint of three little old ladies who had gone to Ryan's tuft investment offices and handed over to the girls behind the counter a bit of their savings and were upset at the loss. (Folk had a bottomless pool of victims to draw upon in his pursuit of Ryan.)


St. Louis Post-Dispatch—Folk Running For Office

Joe Folk's Campaign Slogan


New York Times, July 27, 1904

(At this time Big Tim was a Congressman)

New York Times, July 28, 1904

New York Times, July 29, 1904

(Jack was far down the winnings list in rank

He made his money orchrestrating betting coups,

not betting on his own horses.)

In the company of St. Louis detective Killian, Ryan now boards the Wabash Flyer and makes a speed run to St. Louis. Presumably along the way he stops in Columbus, Ohio, and visits the penitentiary, but this is doubtful.

Cincinnati Enquirer, July 29, 1904

Arriving in St. Louis on July 30, Jack is arraigned in the courtroom of Circuit Judge Foster and posts bond through the kind offices of his wife Anna's sister, Mary O'Leary, now married to John Moloney. Mary was a school teacher at this time, who somehow appears to have accumulated several pieces of rental property and it is this that she posts on Jack's behalf. (This is the same Mary Moloney who—for one dollar—ends up, in 1905, the owner of Jack's Elkton horse farm that was sold at Sheriff's sale in 1903 for $7,000, and her husband, John, will appear as the strawman owner of several properties Jack controlled.)

Mary Moloney's property put up for Jack, or was it Jack's?

Two days later—his trial conveniently postponed by Folk til after the November elections—Jack is back in New York, in time for Saratoga. But he skips the experience by taking passage to Europe with his fourteen year old daughter, Marie. Though at some point Jack left Marie in Ireland with a priest, as she told it he took her to Madam Kelly's famous Paris brothel first; and, near dawn, to the Pigalle and the House of All Nations where the entry doors handles, she said, were erect penises. But, at eighty-seven when she said this, she may have mixed the latter memory with Madam Burt's famous old place across from New Orleans, in Storyville. Marie was a pistol, a splitting image of her father. A hour after first meeting her, we were sitting at the bar of Harrison's Landing, in Lauderdale, and she was knocking down straight shots of whiskey.


New York Evening Sun, August 2, 1904

New York Evening Sun, August 13, 1904

12 Rue Chabanais, today 

La Cabanais, 1904 Lautrec 

La Chanbanais Yesterday 

New York Evening Sun, September 28, 1904 

New York Evening Sun, Sept. 29, 1904

Syracuse Telegram, November 1, 1904

At the end of November 1904, with Joe Folk now the newly elected governor of Missouri, sweeping with him into state office Jack's old enemy Snake Kinney, Jack left New York and returned to Cincinnati where he remained until February, 1905, when he was called to St. Louis to face his second criminal trial.

St. Louis Post-Dispatch, November 15, 1904

Fortunately for Jack, during the months since his arrest, with Folk concentrating on winning an election, no one in his office spent any substantial time digging into the facts of the State's case against Jack; and so again, as it happened in Judge Ryan's courtroom, Ryan walked.

Jack Gives an Interview



St. Louis Post-Dispatch, February 9, 1905

St. Louis Republic, Feb. 9, 1905

Finally St. Louis has had its last shot at Jack and he again walks free. But what exactly does he walk with? It's difficult to know. Though he appears to have been a solo operator, more likely the reality is that he represented the public front of a syndicate. He must have had some help from Sullivan and the Considines, in the operation of the Iron Hill Race Track, in his decision to return to St. Louis in 1900 and try to muscle his way into the city's ward politics, his giving the effort up and leaving town; then, just a matter of months later, he returns with his turf investment business. He certainly had employees to pay, which he did since some of them—O.W. Deppeler, for example—were still working deals with him as late as 1918. And it's hard not to believe George and John Considine, along with Big Tim, didn't share in the take. And, given his connection to Hot Springs, Arkansas, shown by his interest in the Arkansas Club, one must wonder whether Ryan had a  relationship with E.J. Arnold, using him to set the racket up, prepare the suckers for the coup de grâce; after all, it was Arnold who, coming first, drew the suckers in, with the offer of a five percent return on investment per week, with the right to withdraw principal without notice; then, when he cut the percentage down to 2%, Jack appears offering 5% and the suckers withdraw the money in droves from Arnold and take it to Ryan, not reading the fine print of the subscription agreement that stipulates 30 days notice is required for withdrawal of principal. This, of course, causes Arnold's operation to apparently collapse and in a matter of a few weeks brings Ryan's down with it, but in those ten little weeks in between Ryan scooped up a million dollars of St. Louis money and walked.

Proof is hard to get at this late date, but Arnold's purchase of the famous thoroughbred, Gold Heels, from Diamond Jim Brady, as a publicity stunt, then the horse's return to the East after the game is over, carries a whiff of conspiracy with it.

A few years later, disgruntled subscribers found Arnold running a livery stable in Indian Territory. They sued him there in federal court but the outcome has gone unrecorded and, unlike Jack, Arnold and his wife disappear from history at this point. It's easy to believe they passed a long enjoyable life together as Mr. and Mrs. Smith.

When Jack walked out of Judge Foster's courtroom, shaking hands with the lawyers who got him out of it unscathed, he knew he was a rich man and a free man. Leaving the lawyers behind, he walked alone the three blocks up Market Street to Union Station, and boarded the Wabash Flyer for the five hour trip to Cincinnati. In his seat, watching the flat Midwestern countryside roll by, what did he think he would do with the rest of his life?

The first thought surely would have been the simplest: he would manage his money conservatively, invest it prudently, let it work its magic through interest earned and profit taken, and live reasonably within its means; perhaps educate himself in the classics, take long walks, travel with his wife, enjoy watching his daughters grow up, involve himself in chartiable works, take a stab at Cincinnati politics. Read Shakespeare. But that would mean leaving the gambling game behind, the exciting, nerve wracking swing of fortune behind, his fame behind. Riley Grannon standing on his stool in the Brighton Beach betting ring, shouting down at the mob of bettors crushing round him—Beat me if you can!

With what he didn't put in real estate, what Jack did do, is invest some of his money in the legitimate theater business, and some of it in the gambling business, run through roadhouses and clubs.

By 1905, from the income he received from his Seattle box halls, John W. Considine had built a chain of vaudeville theaters through Oregon and Washington states, with an outpost at San Francisco. He did this with several competitors nagging at his coattails, among them John Cort and twenty-nine year old Alexander Pantages. Pantages, in particular, was dogging him by taking profit from ten cent admission flicker theaters he had set up in empty retail spaces next door to Considine theaters, and expanding with vaudeville theaters in competition to his. The competition became hard-edged when Pantages and Cort attempted to monopolize the bookings of the first class vaudeville acts by entering into an exclusive arrangement with the Western Booking Association which controlled, or attempted to control, the booking of all acts west of the Mississippi River.

To break the monopoly, Considine reached out to Big Tim Sullivan who, with a man named Kraus, controlled much of the vaudeville theaters and music halls in New York, and operated a vaudeville circuit on the East Coast. Big Tim was intimately connected with William Morris, the most popular independent booking agent of the day, William Fox, Marcus Lowe, and other fledging motion picture producers, and could supply through Morris the bookings Considine need. As a consequence, the Sullivan-Considine Circuit was formed in early 1905; beginning as a circuit with about twenty theaters, all of them in the western states, by 1912, it expanded to include over fifty and the newspapers were calling Considine, "King John."


John W. Considine
John W. Considine, 1906
Big Tim Sullivan
Big Tim Sullivan, 1906


In 1910, Big Tim wanted to fill in the gap between Considine's houses west of the Mississippi and his in New York, so he brought Jack into the business by joining with Considine as stockholders in several companies Jack had incorporated— the Olympic Theater Co., the Empress Theater Co., the Orpheum Theater Co.—and bringing Jack into their booking agency as a stockholder and director.

Jack purchased a lot in downtown Cincinnati and built a 700 seat theater he named the Olympic Theater. Soon after its construction was completed, the business group which controlled existing vaudeville theaters in the city, led by the city's political boss, George Cox, and Major Max Fleischmann, entered into a contract with Ryan in which it was agreed that, in exchange for the group leasing the new theater for ten years, Ryan promised not to compete with the group in the vaudeville business. No sooner was the ink dry on that contract, but Ryan used his brother, Ed, as a front, to begin construction on another vaudeville theater in the city. Fleshing out his string, with Sullivan as his silent partner putting in cash, Jack bought or build theaters through 1912, playing vaudeville and motion pictures, in Covington, Ky, Indianapolis, St. Louis and elsewhere.

Colonial Theater, Indianapolis

(the building included a hotel)

Olympic Theater, Cincinnati

Colonial Theater, Covington, KY

Jack also established theaters intended for vaudeville in Erie and Scranton, Pennsylvania, and Albany and Buffalo, New York, but it appears these were not successful enterprises and they were soon abandoned. How much money was lost in the transactions and whose it was, the record does not show.

At the same time Jack was organizing his theater business, he continued to appear at the tracks, though his welcome was wearing thin and, in any event, the political atmosphere was turning against legalized wagering on horse races, no doubt in large measure because of the public notoriety of plungers like Jack.

The last of Jack's betting coups seems to be his use of a horse named Athlone (Athlone is a town on the Shannon in Ireland.) Athlone was raced in the spring of 1905 on the Latonia track and had some wins when ridden by a jockey named U.S. Wishard. Athlone's run began on May 25, when as a 12 to 1 shot, he stole up on the leader in the stretch, and, in a driving finish, won by half a length. A day later, in a driving run at the finish, going neck and neck with the winner, he placed. The day after that, though, Athlone appears to have been the medium of a well-planned coup, with a horse named Autolite from 15 to 25 to 1 being well played just before post time by a crowd which evidently knew what it was about.

Latonia, June 7, 1905

In the first race Athlone started well, getting well up in the pack, and closed strong in the final strides on the leader, and got in front just in time to cross the wire. On June 11, he won again on a strong showing, but on the 25th, ahead for the meat of the race he tired in the last quarter and fell to show at the line, and the next day, Wishard not riding, he ran out of the money.

June 26, 1905

Now it appears some funny business occurred, with Ryan allegedly buying the horse from its owner, then selling it to jockey Wishard, who took it to Saratoga where Ryan on August 7, in the fifth race, made another killing.

New York Times, Race Summary, August 7, 1905

New York Times, August 7, 1905

New York Tribune, August 8, 1905

The unevenness of Athlone racing performance at Saratoga, of course, prompted the outcry that Ryan had pulled a fast one again—the assumption being that the jockey must have held the horse back in his first showing, to trick the official handicapper into thinking he was not in his class and giving him less weight to carry which allowed him to run through the second field. The outrage at the state of the racing game in general, and at Ryan in particular, is evident from the article the successful sporting magazine—The Outing—published shortly thereafter.

But the criticism is not necessarily altogether fair, as the famous plunger, Pittsburg Phil, points out, in his book, Racing Maxims and Methods: "it is a fact that the condition of a horse in a race has considerably more to do with his winning or losing than the weight he carries. For instance, a horse carrying 110 pounds in one race might beat the top weight carrying 126 pounds; yet in the next race the condition of the top weight might be so improved that he would run away from the horse that beat him in the first race. Because of this many people attribute the result of a race to crookedness when it is nothing more nor less than the good condition of one horse and the lack of condition of another." 

Athlone was well known to Kentuckians, he was a stranger to the eastern men and it is easy to see how his poor performance the first time out at Saratoga might have induced the official handicapper to assign him less weight, and the bookies to write him off as an also ran. Who knows whether Athlone ran poorly because that's what Jack wanted, or because he was that day outclassed? In any case, Jack's presence in the betting ring of race tracks more and more was becoming offensive to the stewards of the jockey clubs and the old millionaries that were the racing trust.

Jack Up in The Dough

Chicago Tribune, August 12, 1905

Through 1906, it seems Jack concentrated his attention on his theater business, working hand-in-hand with John Considine, who was the active partner running the Sullivan-Considine Circuit. (It seems though Sullivan made a lot of money over the table and under it, his record-keeping proved to be nonexistent, to say his accounting was sloppy is an understatement)

Variety, June 20, 1906

Variety, June 20, 1906

The New York Clipper, July 28, 1906

Variety, September 17, 1906

Variety, Dividing Up The Vaudeville Pie

Variety, November 1, 1906

Variety, November 24, 1906

Variety, November 24, 1906

Variety, November 30, 1906 

Variety, December 14, 1906

Variety, December 1, 1906

Variety, December 22, 1906

So far, apparently so good, despite a misstep or two: Jack spend the fall of 1905 and all of 1906 devoting the substantial part of his time to buying properties in several Midwestern cities, building and leasing theaters, both for himself and in alliance with Sullivan and Considine. In Cincinnati, he sagaciously secured a ten year lease for the newly built Olympic Theater from the business group already established in vaudeville there, but then immediately made plans to build yet another theater—this one called the Century Theater—to compete with the Cincinnati group to whom he had leased the Olympic Theater. And then, abruptly, he announced he was taking his wife and oldest daughter, Marie, around the world. Whether this was a surprise to his partners the record does not show.

Variety, January 4, 1907

Variety, January 4, 1907

The announcement is surprising. Jack has just leaped from the world he knew like the back of his hand, the hard world of gambling in the pit, and now, with who knows exactly how much of a hard won million in his hands, he seems to have dumped a large measure of it in the theater entertainment game—a game neither he nor his brother, Ed, knew anything much about. And if the horse race game was tough, as much could be said about the theater business of the time.

The problem was in the booking: an all out war was going on, between Considine and Pantages on the Coast, each cutting each other's throat any chance they got, with the United Booking Agency, a combination of the Western Vaudeville Association and the B.F. Keith Booking Agency, providing the players with a guarantee of 57 weeks of continuous employment. Against this Considine could offer 40 weeks of work, drawing players through the offices of William Morris. To make the offer as attractive as what the United Booking Agency could offer, Considine needed to give the players a number of weeks of work east of the Missisippi and he was counting on Jack's management of the string of theaters in Missouri, Indiana, Ohio, and Pennsylvania to do that. At the same time, fierce competition for players between rival houses in every eastern city made it crucial that the managers of Jack's theaters were performing at a competitive level; that advertisements were being correctly made, that acts were being booked that would attract the public, the players were being kept happy in their rotations, and the bills were being paid.

Who can say that Jack's brother, Ed, would not keep the organization in good order, effectively handle the several ribbons of the business, meet contingencies as they happened, keep the competition at bay, even gain inroads against them? Still, it seems that Jack was taking a risk, leaving such a large enterprise he had barely just organized in the hands of anyone but himself. Well, no matter; off he went.

By the middle of January he was in Los Angeles, with Anna and Marie, betting on the Ascot races. Then he went up the coast, stopped at San Francisco for a few days, and on to Seattle where he met up with his pal, John Considine, obtained a passport and boarded J.J. Hill's massive ocean liner, S.S. Dakota, and sailed to Tokyo, with a short stay on Ohau. On the way out of Japan, though, as Marie put it one night as we drove along Lake St. Clair in the Seventies, the Dakota sunk.

S.S. Dakota

American Marine Engineer

Jack's Report to the New York Times

Washington Post

Jack around the world

So what next for Jack, before he meets up with Chris Smith? A bar room brawl, one last trip to the betting ring and a street fight, a manslaugher charge, an indictment for engaging in the bucket shop game.

The Bar Room Brawl

Washington Post, Oct. 3, 1907

Cincinnati Enquirer, Oct. 3, 1907

Realizing his act was indefensible, Jack sent Ed to Murphy's lawyer with a $5,000 offer to settle the suit for damages Murphy had filed. Murphy rejected the offer and the case went to trial, resulting in a jury verdict in Murphy's favor in the amount of $3,000.

Jack's final Episodes in the Betting Ring

New Orleans Picayune, Jan 1908

Racing Form News, Jan 1908

New Orleans Courier-Journal, Jan 1908

New Orleans Courier-Journal, Jan 1908


The Street Fight

Saint Charles Hotel, New Orleans, 1908

New Orleans Courier-Journal, Jan. 1908

New Orleans Courier-Journal, Jan 1908

Racing Form News, April 1908

Saying so long to New Orleans track betting, Jack loaded his 1908 Fiat touring car, brought back to the States from his world travels, onto a train and returned to Cincinnati. But, notwithstanding his public pronouncement of retirement from the betting ring, Jack continued to launch betting coups through the remainder of 1908, even partnering again with the manager of his old St. Louis Turf Investment Co. office, one O.W. Deppeler—a man who it appears Jack maintained a long relationship with. Indeed, it is clear by now that Jack was the public face of a group of gamblers, confidence men, bookmakers, whatever you want to call them, which invested in various betting coup operations, including his, over a twenty year period.

Washington Post, May 8, 1908

Jack Looks For Headlines in Auto Racing

At the time Jack returned to Cincinnati, in 1908, Barney Oldfield was barnstorming the Midwest in his famous Stearns 88—the Green Dragon. Oldfield emerged as a national personality at the 1904 St. Louis World's Fair, where, in a race, he lost control of his automobile and, crashing through a fence, killed two bystanders. In the years afer, he made his living going from town to town, exhibiting his racing vehicles and engaging in races on and off tracks.

Oldfield Behind the Wheel of his "88"

Since 1903, when he first appeared at Saratoga in the dough, Jack had been racing about on the public streets in high powered automobiles, and this led to his entering long distance races which were the fad of the day, at Daytona, Atlantic City and elsewhere. So it is not surprising to find that, in returning to Cincinnati in 1908,  Jack felt compelled to challenge Oldfield to a match race to be held at the Latonia Race Track; no doubt Jack saw himself behind the wheel roaring around the track, hub to hub with Oldfield as the grandstand crowd cheered.

Jack Behind the Wheel of His Stearns' Racer, 1908

St. Louis Post-Dispatch, August 8, 1908

Cincinnati Enquirer, August 12, 1908

 Soon after Oldfield accepted the challenge, however,  Jack had gone into the Kentucky countryside of Campbell County, on the road between Lexington and Covington, his automobile filled with friends, and roared his big beast up a long, steep grade toward the ridge that takes the road into town. As he neared the top, his friends laughing and cavorting, he sees a man about to cross the road some yards distant in front, and he pounds on the horn and everybody yells as the fat side lamp on the passenger side shatters in its collusion with the man's head.  Jack is arrested for manslaughter when the deaf mute dies, but the criminal matter is dropped when Jack sends Ed to settle with the family for $3,000.

Cincinnati Enquirer, August 16, 1908

Cincinnati Enquirer, August 19, 1908


Cincinnati Enquirer, August 18, 1908

Louisville Courier, April 1, 1909

Again Jack walked; though it appears the experience of killing a pedestrian did sober him up, at least to the point that he gave up his interest in racing automobiles, it seems to have had no effect on his mind set as to where he was going in his life. For, even though he was heavily invested in commercial real estate and was closely connected to major players in the legitimate theater business, in 1909 he chose to be a "broker" of stocks and bonds which resulted in his indictment and arrest for running an illegal "bucket shop."

End of Part V