Jim O’Leary’s Saloon

Lakeside Annual Directory of the City of Chicago, 1904

O’Leary James J

Chicago Tribune, January 31, 1895

Although gambling has been suppressed. in Chicago policemen from the Central Station last night succeeded in arresting 179 men in one gaming resort. There were nearly 300 men in the place when the police entered, out in the scramble that followed fully 100 got away by means of the windows. The place raided was the pool room in the rear of the saloon No. 4147 Halsted street. It is run by James O’Leary, whose first claim to distinction is the fact that it was his mother’s cow that set Chicago on fire back in 1871.

O’Leary formerly ran a mammoth gambling-house over his saloon, but in deference to the Civic Federation and public opinion he closed it some monthe ago. To keep up his income he opened the pool-room. Trade soon became so good that there was not room enough for the patrons and O’Leary bought a frame house which he moved to the rear of his saloon. The saloon building is of brick, but O’Leary cut a hole in the wall and one in that of the frame building. Through this impromptu door this patrons of the saloon could reach the pool-room. This room was nearly sixty feet square. Across one end was built a platform inclosed by iron raiiings and on this sat the clerks and ticket writers. Huge blackboards on the wall were arranged for the entries of hordes in all races at Alexandria, Madison, New Orleans, and San Francisco.

O’Leary has been doing a rushing business, and yesterday Inspector Shea detailed Detectives Grace, McClain, Nolan, and Alexander to put a stop to the play. Securing the aid of Lieut. Fitzpatrick and some policemen of the Forty-seventh Street Station, they went to the saloon. As the detectives entered the rear door the policemen in uniform walked in through the saloon. At the sight of the police the men in the place made a wild rush for doors and windows. The handful of policemen seemed almost helpless in the rush. but they succeeded in holding the doors shut. Fully a hundred men climbed through the windows and escaped. O’Leary and the clerks were the first ones seized. As soon as he was arrested O’Leary called to the inmates of the place to give themselves up and that he would take care of them. Acting on this advice they allowed themselves to be taken to the patrol wagon and carted to the police station. It required eighteen trips of the wagon to get all the men from the pool-room. At the station O’Leary, John W. Cella, Patrick O’Leary, and Charles Gilsey were booked as keepers. Michael McInerney was on hand and bailed them out. O’Leary then began the work of filling out and signing bonds for the men arrested in his place. This occupied him until nearly midnight.

Chicago Tribune, January 16, 1904

With James O’Leary enrolled as a member, the new gambling combination has reapportioned the city handbook and poolroom privileges among those on the inner ring and established a clearing house in the wilds of Dunning, from which the race results are transmitted to the downtown and north side resorts.

During more than a month a little cottage at 2483 Irving Park boulevard, has served the combination as a safe place to receive its track reports over the Western Union wires and send them into Chicago by telephone. The police have been trying to find the place and when they succeeded two days ago they discovered it was outside the etty limits and in the bailiwick of Sheriff Barrett.

The detectives sent by Inspector Wheeler reported that the clearing house was run In the interests of Mont Further developments proved that the place was controlled by the combination of Charles Smith, Harry Perry, Bud White. Tom Magian’s, and James O’Leary.

Cottage Near Poorhouse.
The cottage where the results are received and transmitted to the downtown offices is near the county poorhouse at Dunning. It stands alone in what once was a cabbage patch and shows signs of having weathered many storms.

Two Western union and one telephone wire run from the poles on Irving Park boulevard to a kitchen window on the west side of the cottage. Inside, these are connected to a Morse machine and to a telephone, which has no number. An operator and a boy are in charge of the place.

“They have frightened entire neighborhood.” said Chris Weitz, a farmer. “They told they were running a cigar factory. Then we became suspicious and notified the police that the men must be gamblers and we wanted them put out.”

Returns Sent to State Street.
It developed that most of the returns are telephoned to a saloon on State street, near Van Buren. This has been adopted by the combination as its headquarters, and from it the operator gets his orders. He refused yesterday to give any information regarding these, saying that they dealt solely with the manner in which he is to cultivate the three acres that surround the cottage. The place is owned by A. Sheahorn.

“We heard of the place weeks ago, and detectives were detailed look into the case,” said Inspector Wheeler yesterday. “From their reports I feel absolutely sure that the house is used by the gambling interests of the city. It is my personal opinion that Mont Tennes is back of it.”

May Appeal to Courts.
The objections of the residents of Dunning to the “clearing house” may reach the courts if Sheriff Barrett refuses to make the combination close it. The right to such an appeal was sustained last Wednesday by the Appellate court, which decided that poolrooms are public nuisances, and the attorney general has a right to secure injunctions against them. The decision was in a case instituted against the Madison Turf exchange, a poolroom, at Venice, IIL.

Inside a typical Chicago “poolroom” which was a place where gamblers pooled their money on bets.

Inter Ocean, April 29, 1904

The lid is off! After five weeks’ successful work dona by the twelve detectives who compose the gambling detail and take their orders from Assistant Chief of Police Schuettler, the fight against the hand book makers is to end. Political reasons have forced Mayor Harrison to rescind the orders he has issued and to stop the campaign against them. After Monday there will be little work for the gambling detail. Its members will be told to go slow, and while the, “little fellows” will still keep under cover, the big ones wilt have nothing to fear.

O’Leary to Regain License.
Not only is the campaign to end, but the work already done is to be undone as far as possible. “Jim” O’Leary, head of the gambling trust, whose saloon license was revoked, is to get it back. He will again be allowed to conduct his liquor business at his “palace” at 4187 South Halsted street.

O’Leary is now shouting for Harrison and aiding the mayor in his fight for control of the next state convention. His opposition to the mayor, openly announced after the order revoking his license, disappeared in a night. O’Leary and his followers are now boasting that everything has been “fixed,” and that after the Democratic primaries. which are to take place on Monday, they will again be “doing business” as they did before the gambling crusade started.

It is regarded as more than a coincidence both by politicians and gamblers that the change of O’Leary’s political opinions followed a conference between Alderman Thomas Carey and the mayor, which took place Wednesday afternoon. Despite his claims to be friendly to Hearst, the chairman of the Democratic county central committee is still friendly with the mayor, as he has always been.

How O’Leary “squared” himself with the mayor is a long story. Politics played a prominent part in it. It is said that the settlement means that Edward M. Cummings. one of Carey’s former lieutenants, is to retire as oil inspector, to be succeeded by William O’Connell, present gas inspector, who, in turn, is to be succeeded by Frank Kilcraine of the Twentieth ward. Aa alleged contribution of $10,000, which is to be made to the campaign fund of William Preston Harrison, who is running for Congress in the Eighth district, figures in the story of the settlement with O’Leary.

Heyday af Gamblers.
But no matter the settlement was made, it is certain that O’Leary believes he is going to get back his license, and that there will be no interference with the 23 hand books which he controls. The O’Leary interests are the largest of their kind in the city, and if they are let alone it means much to the sporting fraternity.

Other gamblers will have as little trouble as O’Leary, however. The Perry and Smith combination, which started the fight against O’Leary and precipitated the gambling crusade, but has since come to an arrangement with him, has never been interfered with to any great extent. Neither has the combination which controls the privileges in the Hyde Park district, and which is said to bo headed by Edward F. Brennan, saloon-keeper and Democratic county central committeeman, who is now working with Henry Barrett Chamberlain, former secretary of the Municipal Voters’ league, to put the Seventh ward in the Harrison column. The Brennan combination controls thirty-six hand books.

On the North and West Sides and in the down town district the gamblers who do not belong to the O’Leary-Perry and Smith combination will make their own terms. On the North Side Mont Tennes, who controls eight hand books, and William Brockman, who controls twenty, believe they will be able to do business unhampered. On the West Side the combination said to be headed by William Skidmore and former Senator Broderlck is still likely to have Its hand books interfered with by the gambling detail. The same is true of the hand books run by “Kid” Weller, “Tom” McGinnis, and other independent gamblers, as well as those run by men who have only money enough to back one book.

Most Observe “Appearances.”
The indications of the’ end of the crusade are already numerous, although it has been settled that it will continue until a few days after the Democratic primaries, it being argued that it would not look well to lake the “lid off” until then.

Henry Jenkins, a negro porter employed la Mont Tennes’ place, at 123 Clark street, was yesterday taken before Justice Martin for assaulting one of 150 men who were cashing bets on the races in the poolroom. The evidence showed that gambling was still going on in Tennes’ place.

The arrest was made by a constable, not by a policeman. I. J. Nordlinger, the complainant against Jenkins, claimed he had placed a $20 bet on a favorite and had won. He was standing in line with 150 other persons waiting to “cash in” when he was assaulted.

The end of the gambling crusade will prove a disappointment to Assistant Chief Schuettler, who has worked energetically for five weeks to suppress hand books. The assistant chief obeyed his orders, and the results of the work are shows by the table compiled from his report.

But even Assistant Chief Schuettler is convinced that the influences behind the gamblers are too strong to be successfully fought.

“Gambling and hand books can never be completely suppressed,” he said yesterday. “In the first place the laws prevent successful prosecution of a campaign against the hand book men. There are other reasons why the work is hard.

“I do not pretend that gambling has been entirely suppressed. I do claim, however, that at present you cannot place a bet unless you are well known to the bookmaker. I believe too. that the 1,031 arrests we made have had to effect of keeping young men out of the poolrooms. They are afraid of being arrested,

Cost Bookmakers $140,000.
“I understand our campaign has cost the bookmakers a cool $140,000. The ‘gambling trust,’ I understand, originally raised $100,000 to support the books during the fight. This sum was used and another $100,000 was raised, and $40,000 of this money has gone. Books that made $1,000 a day before tho orders to suppress them were issued now make as little as $50 a day.”

Schuettler denies that the campaign against the bookmakers was a crusade. He says be simply received orders to suppress hand books and obeyed.

He also indignantly denied that the campaign was being waged to assist one faction of gamblers to drive another faction out of business. “Any one who says that is an infernal liar.”

The gamblers themselves say that the assistant chief is correct and that while the campaign may have been begun because of a fight between them, it is not being carried on for that reason now. They say the dispute was arranged long ago.

It was undoubtedly the fight between the two factions of gamblers that existed some time ago that brought about the gambling crusade which is to be ended after the Democratic primaries, unless the fear occasioned by the disclosure or the arrangement prevents it. At the time the fight began the gamblers were divided into two hostile ramps. One clique was headed by the O’Leary interests the ether by Perry & Smith.

Used Bombs and Constables.
The two rival factions waged bitter warfare against each other. Each hired constables who raided the other faction’s resorts, making arrests by the score. The campaign even went so far as to result in the hurling of bombs at gambling resorts. These bombs were generally not dangerous, but were exploded simply to call attention to the fact that the place in which they were thrown was a gambling resort.

While the fight was at its height the “graft” committee began its work. Then the city officials saw that it would be impossible for them to allow things to continue as they had been and the campaign was begun. Twelve men were detailed to work under Schuettler orders and to arrest the men were running hand books. The gambling detail found its work handicapped by the use of telephones by the gamblers. They then began to tear them out and compel the telephone company to remove them.

“All factions of gamblers have suffered equally,” said Schuettler. “I did not plan it so, but I am glad it has happened that my men have raided places belonging to all of the combinations.”

O’Leary’s license wss revoked, and so was Mont Tennes. Skidmore’s places were raided and so were those of Perry & Smith, “Kid” Weller, and others suffered.

Eight Licenses Revoked.
In all, eight licenses were revoked during the campaign. How many of these are to be restored as O’Leary’s is to be unknown. The saloons closed were:

“I have prepared another list of licenses to be revoked, which 1 will send to the mayor in a few days,” said Schuettler, yesterday, “I recommend he revocation of a man’s license only when one of my men actually places a bet and cashes it in the place. If I did otherwise we would not have sufficient evidence on which to work when in court.”

The gambling detail concerns itself only with hand books and does not interfere with poker clubs. These clubs are sow running at full blast in all parts of the city and no attempt is made to interfere with them.

Want to Play Poker? Here’s Where.
At the Owensboro club, 110 Madison street, the Hoffman club, 114 Monroe street; the Milton club, 208 State street; the Marlborough club, 2Z3 State street; Smith & Perry’s Empire saloon, 260 State street; John Broderick’s saloon, at 175 West Madison street, and John Roger’s saloon, 343 West Madison street, poker games were running all day yesterday.

Cases against gamblers called up in police courts yesterday were dismissed at the request of the city’s lawyers, either because they claimed that evidence against the gambler was lacking or they had bees indicted by the grand jury.

The only two cases tried were those against Charles Rever, 3 Clark street, and John Murphy, Randolph and State streets. Murphy was acquitted and Rever was fined $1 and costs.

Three alleged gambling-houses were raided by detectives yesterday. In a saloon owned by Stanley Clomski, at 84 La Salle street, two women, who are said by the police to have been used to entice feminine patrons to the place, ware arrested. The hand book in the place is said to have been operated by Daniel Burns. Burns was arrested, together with Frank Brown, Isabel Brown, and Edith White.

At 84 Adams street, room 51, Abe Arndt was arrested and charged with operating a hand book. The Enterprise buffet, 174 Madison street. was also raided and Edward Barnes was arrested, charged with operating a hand book there.

Chicago Tribune, December 31, 1921

O’Leary’s Saloon Closed.
Jim O’Leary’s famous saloon in the stockyards district was finally closed by the court yesterday, owing to failure by the defendants to comply with legal requirements attendant on the appeal.

Search of the records in federal courts disclosed that more than 190 saloons annually have ceased existence since the injunctions petitions were first filed. These are saloons which were closed and since that time have been reopened under the sanction of the court for other lines of business. Thirty-four of the injunction writs were appealed.

Chicago American, Date Unknown

A drawing of the interior of O’Leary’s 4183 S Halsted Street establishment. Big Jim revealed its maze of secret rooms and the fact that his gambling operations were conducted in a supposedly vacant building next door when he announced, on 1 December 1911, that the building was for sale and that he was retiring. O’Leary’s saloon housed only law abiding activities and was internally separated from the building next door by double iron doors.

Astutely O’Leary kept his eye on the odds of betting on every issue before the public, figured out what odds he would take, and cashed in on the gamblers both going and coming. When betting in thousands of dollars instead of in hundreds, and with scores of customers from all over Chicago, it is not surprising that O’Leary was able to build a $100,000 mansion in West Garfield boulevard and live the life of an emperor.

Although he had many enemies among those who lost money to him, or whom he delayed in paying. Big Jim had many loyal admirers. As his funeral train slowly moved toward Mount Olivet cemetery in January, 1925, scores of sorrowing friends both rich and poor, in many cases depending on the outcome of their last bets with him, followed the flower-strewn herse. In the words of Michael Kenna, former alderman of the First ward:
“He was a square shooter. Big Jim never welshed on a bet. He was a good loser and his patrons had confidence in him that he would always pay off If he lost. His home life was ideal.”

After his death his joint was taken over by one Toutit, who was proprietor of a saloon there when the place was burned down in last summer’s fire..

NOTES:

In 1904, O’Leary began operating illegal gambling on Lake Michigan with the steamship The City of Traverse. However, without police protection, the ship soon went out of business by 1907 due to repeated police raids whenever the ship had docked. O’Leary however, refused to bribe police and instead had his businesses fortified including the construction of an iron and zinc layered oak door to his resort which were supposedly “fire proof, bomb-proof, and police-proof.” After Chicago crime lord Michael Cassius MacDonald’s death that same year O’Leary gained exclusive control of gambling operations in Chicago’s Southwest Side based in around the Union Stock Yards; in the summer of 1907, Luna Park, opened with O’Leary as its primary owner. The popular park was in operation for four years before its gates were permanently closed.

O’Leary, who had been delivering whiskey to Colosimo’s Cafe under arrangement with Johnny Torrio, was suspected of being involved in the murder of James Colosimo on May 11, 1920. Despite his connection, there were no charges brought against him. By the time of his death in 1925, O’Leary had become a millionaire several times over.

Despite numerous raids by police, he was only found guilty of gambling once during his thirty year career. There was a perception that O’Leary, along with gambling bosses Mont Tennes and “Hot Stove” Jimmy Quinn, controlled the Chicago Police.

O’Leary married Annie McLaughlin, whose family lived in the cottage next to the O’Leary’s at the time of the fire. The couple had five children, two sons and three daughters.

He died on January 23, 1925 in Chicago, Illinois.

Chicago Tribune, March 31, 1935

Mrs. Patrick O’Leary of Chicago fire fame earned her living by selling milk. Her cows and her barn burned up in the great holocaust of 1871.

Jim O’Leary, Mrs. O’Leary’s boy, earned his living in the gambling business. His one-time splendiferous hall at 4183 South Halsted street, with its famous betting buffet, burned up in the great stockyards fire of last summer.

Renowned because of the story of how his mother’s cow kicked the lamp that lit the hay that lit the barn that lit the city of Chicago, eccentric old Jim O’Leary, who died in 1925, possessed plenty of notoriety in his own right. According to his philosophy:

Other folks are burglars. They make their living by stealing. The second-story man, the safe cracker, and the dip are not the only burglars. You’ll find a lot of others In offices in the loop. A fellow that won’t gamble or steal is a beggar.

James Patrick O’Leary was born at 137 De Koven street, the starting point of the fire of ’71. When the catastrophe occurred he was only two, so he could dilate on the subject only from hearsay. Of hearsay, however, there was no derth. Jim always scoffed at the traditional cow’s kick theory of how the fire started. He said his parents had insisted it was a monumental fake, probably started by gossipy neighbors and snatched up by some credulous reporter. Who would be milking a cow at a quarter past nine at night?” asked Jim O’Leary. “The fire started at nine-fifteen, and the cows always were milked at half-past four, when it was light enough so we didn’t need a lamp or lantern at all.”

There have been at least five seriously considered theories as to the fire’s origin.

One of the theories, and the one believed in by members of the O’Leary family themselves, was that the fire was caused by spontaneous combustion. Once reminisced Jim O’Leary:

The day before the fire—it was a Saturday—I helped the old gent (Pop O’Leary) put in some timothy hay in the loft above the cow shed. My part of the job was to stamp it down in the mow. I thought it was great sport. They say that when green hay sweats it causes spontaneous combustion, and that, I heard the old gent often say, was the cause of the fire.

On Monday, Oct. 9, 1871, one hundred thousand people of what had been the flourishing city of Chicago vere homeless and their blackened faces gazed sorrowfully on the smoking embers left after the great fire had burned itself out for lack of fuel. But they did not mourn for long. The new spirit which came to them is well expressed by a Tribune editorial of the following Wednesday, printed in spite of the total destruction of what had been the Tribune office. Said the editorial in part:

Chicago shall rise again

Already contracts have been made for rebuilding some of the burned blocks, and the clearing away of the debris will begin today if the heat is so far subdued that the charred material can be handled. Field, Leiter Co. and John V. Farwell Co. will recommence business today…

We do not belittle the calamity that has befallen us. The world has probably never seen the like of it—certainly not since Moscow burned.

…Ten, twenty years may be required to reconstruct our fair city, but the capital to rebuild it fireproof will be forthcoming… Chicago must rise again.

Young Jim O’Leary, just learning to walk, was rather small to partake in the first surge of reconstruction as Chicago rose again. He was rising for the first time himself. The O’Leary home, curiously enough, survived the great fire, although only forty feet from the barn which started it. But the loss of five cows, a calf, a horse, and everything else that was in the barn fell heavily on the O’Learys; and even harder on sensitive Mrs. O’Leary fell the popular idea that she was personally responsible for the starting of the fire. Neither her protestations nor the fact that Chicago was as inflammable as tinder at that moment could stop the public blame. People forgot that during more than three months of summer heat, from the Fourth of July to the time of the fire, Chicago had had no rain except for an occasional brief shower. They forgot that the very day before the catastrophe, on Saturday, Oct. 7, there had been a $500,000 fire which started in a planing mill at Canal and Adams streets and took the city’s entire fire fighting force to stop. They didn’t realize how much the exhausted condition of the firemen and the low water pressure the following night contributed to the victory of the flames in the final $200,000,000 disaster.

And so Mrs. O’Leary in tears made her husband sell the cottage in De Koven street, and the O’Learys moved to the stockyards district, “where nobody knew them.” A few years later a dime museum manager knocked on Mrs. O’Leary’s door with flattering offers If she would exhibit herself with a cow. She slammed the door in the man’s face. When later an agent sent by P. T. Barnum called to see if she would tour with his circus, Mrs. O’Leary picked up a broomstick and furiously herded the man out the door. She died in a little cottage in South Halsted street in 1895 with (according to neighbors) a broken heart.

Meanwhile son Jim was growing to manhood, at work in the stockyards. On account of his ample frame, flesh, and prowess he was called Big Jim.

In the early ’90’s he opened a saloon in Halsted street near the entrance to the stockyards. It wasn’t long before he added to his equipment a handbook for betting on the races. Presently his place became a regular rendezvous for followers of the turf. He branched out Into other fields of gambling, prospering with astonishing ease.

In a few years he built his palatial gambling temple and saloon at 4183 South Halsted street. At about the same time he built a brownstone residence in West Garfield boulevard that became one of the “show places” of the south side. By the turn of the century Big Jim had made books in his mart of chance on every speculative issue from who’s going to be the next President to whether it’s going to rain or shine next week-end. His joint, the best-known place of its kind in Chicago, was once described by a visitor in the following words:

A big electric sign bearing the name ‘O’Leary’ winked steadily and a fat individual with a huge megaphone stood beneath it bawling out a summons to enter: ‘Concert inside—all free, all free!

The visitor, who approached the front entrance, saw three women wearing gaudy hats” walk inm ahead of him. They were without escorts and swung past the bar as though it was part of their daily promenade. Men were drinking, and a hard-faced blond man hovered about a board on which was marked: ‘Deneen’s election is contested.’

From the back room was emitted a discord of sounds which presumably was the ‘music’ being advertised by the megaphone man outside. It appeared to come from a group of instruments resembling slot machines which were set up in the rear of the concert room. The room was filled with tables and chairs painted green. Many stockmen and others, apparently strangers in the city, were sitting at the tables.”

Although the date was 1908, “women were plentiful. Among them were the three who had walked jauntily past the bar a few minutes before. They were drinking with the men.”

As a result of his gambling and his reputed “contributing to the delinquency of girls,” Big Jim’s joint was often raided, but it seldom bothered the crafty proprietor. “I’ve been raided a thousand times,” he remarked in 1911, “but I’ve never had a real raid.”

“How about the raid three weeks ago, when the police took more than forty people from your place?” he was asked.

“I stand by my statement,” replied O’Leary, shifting his cigar. “The police never got in the back room that day. I was running a book, but they never got one racing sheet for evidence.”

“Is there any gambling paraphernalia in your place now?” continued his questioner.

“The statute of limitations on gamblers is eighteen months,” said Big Jim characteristically. “I had roulette wheels and some other stuff eighteen months ago.”

With a twitch of his curly mustache O’Leary continued:
“I’ve run every kind of a gambling game. Every time I heard of a new one I learned it and tried it. Nobody can say that O’Leary ever ran a crooked game. This reform wave is sweeping the country, and I think it’s here to stay. If they let me run long enough I’m going to bet on zero weather.

“How much have I cleaned up he mused. “I’m satisfied with the results. I’ve got enough to take a trip around the world when I sell my shop. Then I’m going to settle down in some live little town.”

Although nobody but O’Leary himself and a few trusted employes ever knew where all the exits to his temple of chance were, or even how many there were, and although O’Leary’s son married the daughter of Police Inspector Clancey, who had charge of the “yards” district for many years, Big Jim finally—at the age of 53—got caught, convicted of gambling, and fined $100 as a first offender. He died only three years later, having never been caught in a second offense.

The secret of his success in the gambling business is really no secret at alL It was the old “heads I win, tails you lose” setup, with elaborate, confusing variations. Big Jim was the only one in his joint who didn’t take chances. He invested only in certainties—and became famous as Chicago’s greatest gambler.

NOTES:

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