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The Great Racetrack Caper

June 2024
15min read

The bookies had to get racing data from paddock to betting parlor. All at once some very shady characters began showing up at the entrance to the track

In the entire history of the turf there lias probably never been anything remotely resembling the 1891 spring and fall horse-racing seasons at the old Gravescnd track at Sheepshead Bay in Brooklyn, New York. The extraordinary events that attended the meetings resulted from an economic squeeze play on the part of the Brooklyn Jockey Club, which operated Gravesend. Then, as now, off-track betting was illegal in New York state, but then, as now, it was a popular form of gambling. To keep local betting parlors aware of all the pertinent racing data—post odds, scratches, jockey selections, weights, and results—the Poolsellers Association, a syndicate of Manhattan bookmakers, telegraphed the information direct from the various tracks to the “poolrooms”; for this privilege, the association paid the management of each track S 1,000 a day. When in the spring of 1891 the Brooklyn Jockey Club suddenly decided to quadruple the rate, the bookies refused to pay. Somehow they would bootleg the information out of the track; the Jockey Club could go hang.

Thus began a spectacular running battle between Pinkerton’s Race Track Police, representing the Jockey Club, and members of New York’s remarkably picturesque Gay Nineties underworld, allies of the poolsellcrs’ syndicate. The gamblers were also supported by the Western Union Telegraph Company, which, counting the bookmakers’ association a valued patron, threw into the tray several dozen highly imaginative telegraphers.

The ensuing trackside scrimmages went on for weeks, and became so lively and exhilarating that the racing seemed dull by comparison. Indeed, the sports editors ol New York’s newspapers became so preoccupied detailing Gravcsend’s warlike side show that a racing fan was often hard put to find on the sports pages the simple facts about which horse had won each race. Each day at the track Pinkerton men, some in uniform, others in plain clothes, guarded the gates, locking them once the crowd was inside. But this was a little like latching the hen-house door after the fox had slipped through. For undetected in the crowd, disguiscd as pregnant women, ladies of fashion, gentlemen, or country bumpkins, were a number of gamblers, thieves, dips, touts, and ladies of the evening, allied with the bookmakers and loaded down with all manner of exotic signalling equipment.


As post times nearcd, they wigwagged semaphores and flags, waved umbrellas, walking canes, and handkerchiefs—one woman even waved a baby—to convey racing data to confederates outside the fences; these in turn passed the information on to telegraphers, who relayed it to the poolrooms in Manhattan, several miles away. Shoplifters brought carrier pigeons into the grounds, concealed in the secret pockets of their professional costumes; released with racing data tied to their legs, the birds took wing and headed for the betting emporiums. But beyond the fences, under the birds’ line of Might, marksmen lurked. The Pinkerton detectives were resourceful, too: they captured some of the pigeons inside the park, loaded the birds with incorrect results, and released them. Soon passionate cries of anguish were heard in the betting houses as operators realixed they had been paying off the wrong people, sometimes on horses that had run last.

Out at the track, meanwhile, clubbings, fights, and assorted strife swirled about the beleaguered gates. Frequently the crowd was treated to the stirring spectacle of a squad of sweating Pinkertons in full uniform flashing past the grandstand in pursuit of a fleeing poolroom suspect. All this added xest to the sport of kings; the Gravesend track was something like a castle under siege, with the Marx Brothers in the roles of invadcrs and the Keystone Kops manning ilie ramparts.

The conflict stemmed indirectly from the Ives Law, passed in iH??, which restricted legal beuing in New York state to racetracks. Naturally, the law made hutting with bookies more popular. Jn iMyy Manhattan had only four or five poolrooms, which operated behind barricaded doors equipped with peepholes. My iXyi, however, about sixty betting joints were running wide open. A few of them were pretentious and elegant, with mahogany furniture, gilt mirrors, and thick rugs. But most were big, barnlike places with dirty walls, cracked ceilings, and dusty windows. They ran three to the block in the Bowery as adjuncts to saloons, with dollar bets accounting for the bulk of business. All were packed with bettors six hours a day.

So popular had the poolrooms become, in fact, that the crowds at the tracks declined sharply; by iHyi, the daily fee the tracks collected from the Poolsellers Association did not make up for the loss in attendance.

The Brooklyn Jockey Club was controlled by Philip J. Dwyer and his brother, Michael, former butchers who had become interested in swift horses when they operated “the fastest meat delivery wagons in New York.” Now they owned a celebrated stable of race horses. Phil Dwyer, the club’s president, had a droopy mustache and a greater interest in money than in sport. Operating a racetrack in the red made no sense to him, and so, shortly before Gravcsend opened its 1891 spring season, he met with poolroom representatives and upped the daily fee to $4,000. The syndicate would not go higher than $1,600.

“The Poolroom King,” Peter De Lacy, a top gambler who dressed like a banker, said he considered all betting evil, but if people were going to gamble, it was no worse to do it in poolrooms than at racetracks. “If Phil Dwyer bars Western Union’s operators from the track, as he threatens to do,” De Lacy told the press, “we’ll send in messengers to bring out news of each race. But I don’t take any stock in Dwycr’s bluff. We defy the Dwyers.”

Dwyer was not bluffing. As the spring meeting began, he disconnected all telegraph wires out of Gravesend except one that served the newspapers.

Western Union then rented the old Sleight’s Hotel just outside Gravesend’s entrance and strung in lines. Once a well-known inn, Sleight’s was now a rickety, three-story shell with an old-fashioned cupola overlooking Gravesend’s starting post and home stretch. With what they could see from this vantage point, supplemented by the reports of Dc Lacy’s messengers shuttling in and out of the gates, Western Union telegraphers managed to meet their clients’ needs with few delays.

The Jockey Club president countered by transforming the track into a fortress garrisoned by 130 private policemen under the personal command of Robert A. Pinkerton, who with his brother, “Big Bill,” headed Pinkerton’s National Detective Agency. Until now, newspaper accounts had featured fleecy prose hailing Gravesend’s racing as “spirited,” “delightful,” “splendid,” “positively brilliant.” Then, on the season’s fifth day, the news from the track shifted dramatically from the sports pages to page one. “TRACK A PRISON,” screamed the New York World . “ THOUSANDS PENNED UP ON BROOKLYN RACE COURSE. PINKERTON SLUGGERS CLUB INOFFENSIVE CITIZENS .”

The Pinkertons locked the gates, according to the World , after some eight thousand people had passed in “as guileless as the wide-mouthed shad which the Spring tides sweep into the fishermen’s nets.” The World and the Herald castigated the Jockey Club president as “King Philip, The First” and called the Pinkertons “hybrid policemen” and “chuckle-heads.” Both newspapers recounted in horrendous detail the pitiful appeals of patrons to be let out of the track. “I must get to New York,” one old gentleman shouted. “I have an important engagement.”

“I don’t care a damn about your engagement. Nobody can leave this track,” said the guard. “Them’s my orders.”

The Herald quoted one “big fellow” who begged, “I am ill; I need a doctor. I’ve just had a hemorrhage.” The Pinkertons were unmoved. A woman with a sick baby pleaded to get out, “but the guards were merciless.”

Said an outraged Englishman to an American friend: “You call this a free country, do you? And yet I’m told when I come in here that I can’t leave until ii certain hour. That’s not liberty. It’s tyranny. Wc wouldn’t stand it on the other side.” The World told of a KciHuckian who drew a big horse pistol and walked out grandly while “every Pinkerton in sight sought shelter.” The newspaper added that “the hammering of Pinkerton clubs on other men’s heads sounded like the popping of firecrackers on the Fourth of July.”


The New York Times and the Sun , which were against gambling, called these charges “absurd.” The persons most eager to leave the track, the Times said, “were almost without exception employees of the gambling syndicate or Western Union,” which company “ought to be called to account for violating anti-gambling laws.”

When the locked gates halted direct smuggling of information, the syndicate undertook fancier measures. Its telegraphers in the hotel cupola had a clear view of the paddock but not of the finish line, so operatives inside the gates performed as “horses”: each one held a placard bearing a number corresponding to an entry in each race; after the official results were posted, they galloped across the paddock in the order in which the horses had finished. The watching telegraphers duly transmitted the results. The Pinkertons soon began chasing the horses, who in their scramble to escape were not always able to flee in the proper sequence; transmitting correct results was a problem. Some poolroom agents now equipped themselves with hollow wooden balls; they stuffed these with papers on which were scribbled odds, jockeys, and results; then they flung the balls over the fences, hoping that associates outside would retrieve them. But the Pinkertons patrolled so vigilantly that few balls fell into the hands for which they were intended; some of them struck bystanders on the head, the Time reported, and at least one man was knocked insensible.

The track remained in a state of siege during the rest of the spring meeting. Fighting flared now and then at the gates. The Pinkertons roped off the paddock and continued to chase ball throwers. When the gamblers’ telegraph lines suddenly went dead, the bookmakers claimed sabotage and offered a $5,000 reward for capture of the saboteur.

During that summer, while the track was idle, Dwyer had a sixty-five-foot-high wooden fence built, which completely blocked the view from the hotel’s cupola. The fall meeting was due to open on September 15. A day or so before the opening, the Herald reported a rumor that the syndicate would fly a balloon over Gravesend on each race day, with observers, operators, and a telegraph station in its basket. The poolsellers never actually used the balloon, but the strategy they did employ was perhaps even more spectacular.

At 3 A.M. on opening day, heavy wagons loaded with lumber, men, and tools rolled up to Sleight’s Hotel. The lumber was carried to the hotel’s cupola and the carpenters went to work. The World described their efforts: No circus tent ever went up faster. Ten feet into the air, then a staircase and a landing. Ten feet higher, another staircase, another landing. Another ten feet, another staircase and landing. The carpenters paused for breath.

It was daylight now and the Dwyer forces rallied in a hurry. A group of carpenters set to work to raise the fence still higher. Ten feet more, and the huge structure began to tremble with the weight of the workers. A breeze blew in from the bay and the men’s hats flew off. They climbed down, glad to be on earth again. They looked across at the Western Union tower.

“Give her another story,” commanded the [tower] foreman. The carpenters hammered and knocked together another staircase and ten more feet of altitude. The tower was now forty-two feet above the cupola and its top platform seventy-seven feet from the ground.

Western Union installed four wires and a half dozen operators in the new tower, the World reported, and stationed a guard at the door. In the gamblers’ camp an air of triumph prevailed. Peter De Lacy walked about “with a quiet smile and remarked that he was content.” He magnanimously handed a tendollar bill to some Gravesend employees and told them to “go blow it” on pie and milk. Racing Manager M. J. McKenna of Western Union “looked pleased,” the Sun recounted, as did “Little Abe” Hummel of Howe & Hummel, lawyers for the Poolsellers Association. From Manhattan, reports were arriving that De Lacy’s own poolroom was packed and that business was booming in all the betting places. Racing information was said to be coming in fine.

“The Brooklyn Jockey Club owns the racecourse,” De Lacy declared, “and has the right to withhold its news if it can. But I don’t think the effort will be a success. We need that information and we’re bound to get it.”

But Sleight’s Hotel was so situated that, even from their tower, telegraphers could not see the track’s finish line; in close races they had to guess the winners. Nor could they observe odds and scratches, which the management was now posting under the judge’s stand. When Western Union offered twenty-five dollars to the first person to get the information for each race through to the hotel, racegoers having no connection with either the syndicate or the telegraph company began to fling rubber balls filled with racing data over the fences. But the patrolling Pinkertons foiled most of these efforts.

The detectives also increased their vigilance over those admitted to the track. One day they noticed a tall young man in a close-fitting gray coat behaving strangely near the betting ring. He would button and unbutton his coat, raise and lower his hat, hold his pink sporting sheet at various angles, mop his brow, and bow in different directions. Sure enough, he was signalling post odds to a man seated in a tree outside the grounds who was apparently cooling himself vigorously with a palm-leaf fan. Actually he too was signalling, in Morse code, to observers in the tower. At about that time, the Sun reported, a carrier pigeon fluttered out of the grandstand’s second tier; catching sight of it, the crowd roared, “There it goes!” “There it goes!” Unfortunately, the message it bore had been insecurely fastened to its leg; as the bird circled overhead before streaking for its coop, the paper dropped into the paddock.

By the time the second day’s racing began, telegraph lines had been strung from barns and trees, with sending stations on some flat-topped stumps. The syndicate was reportedly paying $100 a day to a farmer named Young for the use of his two big locust trees as observation posts.

That night the Jockey Club’s carpenters increased the height of the fence that stood in front of Farmer Young’s trees. Next day the telegraphers climbed still higher, and the Gravesend carpenters appeared with more lumber. Lowering his binoculars, the man in the nearest tree shouted down to his telegrapher, “The horses are going to the post for the second race, and the Dwyers are building another fence!”

The World reported that one tree sitter received his signals from a baby, in the care of the “most innocent-looking woman in the grandstand.”

The woman did not look like a regular, and certainly the baby didn’t. It was a golden-haired, chubby little thing. When its mother—or alleged mother—secured the scratches and betting odds for the second race, she went down to within a few feet of the track, spread her shawl upon the ground and proceeded to amuse the baby.

While the little one kicked its heels in the air, filled its little mouth with tiny fingers and said “goo-goo” the young woman waved a green parasol up and down before its delighted eyes. It didn’t make any difference to the baby that each motion of the parasol was a Morse Code dot or dash. And Mr. Dwyer and Mr. Pinkerton stood twenty feet away at the judge’s stand and didn’t suspect a thing. This little by-play was repeated after the second and third races. Then the new fence and a rainstorm broke up the combination.

Meanwhile, at one entrance the gatemen were challenging a woman. One grabbed at her clothes and a pigeon squawked. “Why,” said a detective, “she’s got enough pigeons on her to stock a good-sized loft. That dress has pockets all the way down. We know too much about shop-lifters to be fooled by a game like that.”

Nevertheless, the poolsellers’ lawyers estimated that fully a hundred pigeons were smuggled into the track that day. The Jockey Club reportedly hired “Snapper” Garrison, an unemployed jockey with a reputation as a champion pigeon shot.

Despite such efforts, signallers continued to infest the grounds. Red, white, blue, yellow, and green handkerchiefs fluttered from many points. The Pinkertons hustled a half dozen men out the gate for twirling their mustaches and walking sticks in a “suspicious” manner. One of them charged that he had been degraded when paraded in custody before the grandstand, and announced that he would sue.

The track management further confounded the poolroom forces by concealing the names of entries until twenty minutes before post time for each race. A printer named Eagan was employed to run the information off on slips of paper, using a portable press set up at the track. “The crowd lay in wait for the messengers who distributed the slips and rushed upon them with much scrambling,” the Herald reported.

Gradually, it seemed, the cops were beating the robbers. Conditions at the betting places in Manhattan were dismal. Crowds melted, and the bettors who did come complained loudly of the poor service. At De Lacy’s own place, the announcer said at 2:42 P.M. , “They’re at the post at Brooklyn.” It was thirty-two minutes later when he got the word, “They’re off at Brooklyn!” One place had the horses running in the stretch for two minutes. Some betting rooms posted signs, “Not Responsible For Errors In Weights And Jockeys.” All this encouraged the antigambling Times to headline its lead story: “ POOL MEN BEATEN AT LAST .”

But the poolroom forces had a few tricks left. The next afternoon a pole was set up near Gravesend’s lower turn, its top poking above the fence like the head of a great serpent. A telegrapher climbed on spikes to the crossarm near the top, took off his hat, and bowed solemnly in the direction of President Dwyer’s box. Then he hauled up a telegraph key and fastened it to the pole. “In three minutes,” the Herald reported, “he had a little telegraph office in operation, ninety feet in the air. He was a facetious little man as well as a bold one. No sooner was his shop in order than he pulled a national flag from his pocket and nailed it bravely to the top of the pole.”

That night workmen planted another pole in a yard east of the track. It stood 120 feet high. When its telegrapher reached the top the following day, he was greeted by his colleague atop the shorter pole on the lower turn, who snatched his flag from the mast and waved it around his head.

At this point, the Pinkertons began to raise their own poles within the grounds. Each carried a great spread of canvas, like the mast of a sailing ship, which effectively blocked the views from the poles outside. Even so, the pole sitters returned to their perches on the days that followed, although the Pinkertons were certain they could see nothing of value. Pigeons had been cleared from the grounds, ball-throwing had ceased, and no signallers were in sight.

Still there was a leak somewhere. “By some mysterious means,” said the World , “whether by necromancy, juggling or what, the ‘pool rooms’ yesterday seemed in their normal condition. Betting was in full swing on all the events at Brooklyn. Jockeys, with the exception of the first race, were listed. No one seemed to know how the information from Brooklyn had been obtained.”

Robert Pinkerton and his men managed to unravel the mystery before the fall meeting ended. What they discovered was proclaimed in these World headlines: “ ELECTRICITY IN THE HAT. THE MOST INGENIOUS SCHEME YET FOR OBTAINING RACING NEWS .”

“Every afternoon,” the Herald explained the next day, a “handsome barouche, drawn by a pair of spirited horses, whirled a party of ladies and gentlemen to the lawn just above the betting ring. The driver parked his vehicle at a spot near the track, and the party seemingly turned themselves to enjoying a holiday. They had lunch and wine and cigars in plenty and seemed bent on nothing but enjoying the sweets of life.…”

Had the Pinkertons scrutinized the barouche more carefully, they might have noticed that the coachman wore an unusually tall silk hat and that he kept his seat on the box while members of the party visited the betting ring or viewed the races. They returned to the carriage now and then, ostensibly to refresh themselves. This continued daily until five days before the season ended, when Pinkerton and his men raided the coach. The picnicking group was headed by Joseph W. Frost, an electrician and president of the Automatic Fire Alarm Company, 317 Broadway. He was accompanied by his wife, Eliza, and their ten-yearold son; Frost’s brother, a onetime Indian agent and now manager of a Washington, D.C., hotel; a Mrs. C. A. LaViIIe; and the coachman, C. S. Pearsall, who, not entirely by coincidence, was a telegrapher.

It developed that Joseph Frost had arranged with the syndicate to supply complete racing information from Gravesend to Western Union for $1,000 a day, and he had succeeded in doing so for six days. Pearsail’s tall coachman’s hat had a hole in the center of its top the size of a half dollar. Inside the hat was a small electric light powered by batteries concealed in the coach. Under his clothing Pearsall wore a network of wires that connected the light with the batteries and with a telegraph key hidden on the coach floor.

Members of the party brought him information on odds, jockeys, and the like from the betting ring. The finishes Pearsall observed himself, simply by standing up in the carriage. He sent a running story by operating the key with his foot, causing the light in his hat to go on and off in Morse code. The telegraph operator in the hotel tower could not see the finish line or the posted odds, but he had a fine view of the top of the coachman’s hat. Somehow or other the Pinkertons were tipped off, and suddenly one afternoon Robert Pinkerton himself leaped into the carriage and dragged Frost from it. During the struggle, Mrs. Frost screamed, “Turn that man loosel” and hit Pinkerton (he said later) on the head with her parasol. She claimed that Pinkerton had grabbed her by the throat and choked her. As the party was led away, Frost bellowed, “You’ll suffer for this, as I have the Western Union Telegraph Company and ten million dollars at my back.” The bookmakers left their stands and shouted in excitement. Bettors abandoned the ring and shouted encouragement to the Frosts. One man jumped over the fence, snatched off his coat, and, directing his ire at die Pinkertons, yelled, “Come on and hang ‘em!” The crowd in the ring shouted, “Lynch ‘em!” “Lynch ‘em!”


Fortunately, nobody was lynched, and the carriage episode became the final act of “the Great Battle of Gravesend” as public spectacle. Thereafter, De Lacy and his cohorts resorted to more subtle strategems.

By instituting or backing a number of lawsuits during the decade following 1891, De Lacy secured several lower court decisions holding the Ives Law unconstitutional. Since that law had declared that the only place a man could get down a legal bet was at a racetrack, these findings had the effect, temporarily, of making all betting a crime in the state. Thus, in 1893, De Lacy secured the arrest of Phil Dwyer, by then a millionaire who controlled most of the racing in the metropolitan area, but the charges were dismissed in the higher courts. Meanwhile, track managements were bringing pressure on the police to close the poolrooms. De Lacy’s own place was closed in 1893, but at the turn of the century the tenacious “Poolroom King” was still plaguing racetrack managements with arrests and lawsuits.

The man who came close to wrecking thoroughbred racing in New York state was not De Lacy, however, but the reform governor—and future presidential candidate, Secretary of State, and Chief Justice—Charles Evans Hughes. His administration outlawed all racetrack betting, and that closed every established track in the state after the end of the 1910 season. But racing interests got this law repealed in time to resume in 1913, and the sport of kings has thrived ever since.

Not, however, in Brooklyn: old Gravesend Racetrack, which closed with the others, failed to re-open in 1913. Brooklyn was changing from a center of sport to a “city of homes,” and the land was later sold for real-estate development.

In the past few years, urged on mainly by New York City, which hopes for increased tax revenues, some members of the state legislature have made serious attempts to legalize off-track betting. They have not succeeded to date, but the idea refuses to die. It is possible that after all this time Peter De Lacy may eventually win his point.

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