Horse “ringing” is the practice of running an experienced, faster, or older horse under the name of a younger or nondescript one, usually to take advantage of long betting odds. “King of the Ringers” Paddy Barrie boasted of ringing hundreds of thoroughbreds at racetracks across the United States, in Canada and at Agua Caliente near Tijuana, in the 1920s and early 1930s.Footnote ¹ Journalists agreed that criminal associates in America's major cities made regular use of Barrie's talents, while Pinkerton detectives charged that Barrie's ringers earned millions of dollars for betting rings.Footnote ² The wider American public learned of his exploits following his most famous coup at Havre de Grace, Maryland's premier racetrack, on 3 October 1931. Barrie bought Aknahton, a three-year-old light chestnut colt and experienced racer, for $4,300 from the Marshall Field Stables in Chicago. Shem, a plodding two-year-old gelding of similar colouring, was purchased for $400 from a reputable Long Island trainer.Footnote ³ Barrie then dyed Aknahton to look like Shem, and entered the ringer as a two-year-old maiden on the last racing day at Havre de Grace. The race favourite was Byzantine, owned by Mrs. Payne Whitney, and Shem was given odds of 52–1. After a poor start Shem (aka Aknahton) caught the field, passed Byzantine, and won by a sensational four lengths, guaranteeing winnings of more than $250,000 for Barrie's patrons. Accusations of cheating and suspicions of fraud soon followed, as did official scrutiny of the horse and his trainer.Footnote ⁴

The exposure of a major racetrack corruption ring in the US in 1931–32, with Barrie at the centre, confirmed long-standing popular views that horse racing was dominated by swindlers, thieves and gangsters, and that race fixing was widespread.Footnote ⁵ Bookmakers regularly bribed stable hands, handicappers and timers for information on a horse's form and to calculate odds, while trainers and jockeys were paid to fix races.Footnote ⁶ Doping with cocaine or caffeine to increase pace, inserting sponges into a favourite's nose to hamper breathing, tampering with saddle weights, and affixing heavier racing plates were all used to alter racing performances.Footnote ⁷ A stable boy confessed to administering chloral hydrate to slow down Ladana, the Rancocas entry in the Burnt Hills handicap at Saratoga in August 1931. The horse was disqualified when she “presented with swollen, drooling lips” at the starting gate.Footnote ⁸ Barrie's special recipe of heroin mixed with digitalis, cola nut extract, glycerine and strychnine could be administered orally and by syringe, to Stickaround for example, to ensure a win at Hawthorne, Chicago, in late October 1931.Footnote ⁹

Barrie's forte was colouring horses. It was this skill which made him so valuable to the organized-crime leaders, gangs and syndicates which maintained protection and betting rackets at North American racetracks.Footnote ¹⁰ One Pinkerton report confirmed, “there is so much work to be done to produce a ‘ringer’ that there are not many people who select this particular type of racketeering.”Footnote ¹¹ Detailed descriptions of horses’ colours and markings were recorded for Jockey Club registration and photographic records were rare until the later 1930s. Shem was a dark chestnut horse with a narrow white strip on the face and two white hind socks. Aknahton was a lighter chestnut colour, with a white face stripe, a white left-fore pastern, and two white hind ankles.Footnote ¹² Shades such as dark brown, sorrel, chestnut or bay could be enhanced or altered with dyes, petrol and peroxide. Star, blaze, strip and other white markings on a horse's face and its white heels, coronets or pasterns could also be augmented or created with bleach and paint.Footnote ¹³ Barrie's expertise extended to creating special materials as well as accuracy with the brush. His henna-based dyes withstood repeated washing, and the better the alteration, the less likely it was that the substitute would be detected.Footnote ¹⁴ Many contemporaries, journalists and historians referred to Barrie as “the master painter”; he styled himself “the last of the great artists.”Footnote ¹⁵

In Ringers & Rascals (2003), racing journalist and social historian David Ashforth detailed Barrie's exploits in Australia, Canada, the United States and Britain from the 1910s to the 1960s.Footnote ¹⁶ By contrast, this article includes a short biography but focusses on Barrie's North American criminal career in the 1920s and 1930s, themes of interstate and transnational criminal mobility in the early federal war on crime, and the relationship between professional travelling criminals and big-city organized-crime networks. Smuggling, immigration, and policing studies have highlighted the scale of interwar transatlantic and trans-Pacific illicit networks and criminal migration, and Barrie's story confirms the vibrancy of transnational opportunism and its huge financial rewards.Footnote ¹⁷ He is also a useful example of criminal mobility in an era of increasing immigration restriction and border controls. As Andreas and Nadelmann note, “Criminals who cross these lines sometimes do so with indifference to its jurisdictional consequences; more often, however, they regard the easily crossed borders as an advantage, one that offers lucrative profits to smugglers, safe havens to bandits, fugitives, and filibusters, and economic opportunities to illegal migrants.”Footnote ¹⁸ Jurisdictional borders and sovereign dividing lines were often more limiting for law enforcers than for the offenders they were pursuing.

The Pinkerton National Detective Agency (PNDA) pursued Barrie for three years between October 1931 and his eventual deportation in November 1934. During this period, the agency accumulated a large body of files documenting Barrie's ringers and frauds. Some are almost exclusively of newspaper clippings and typed articles, but surviving investigator reports reveal much about PNDA strategy and methods, and the challenges of investigating a highly mobile con man in a period of nascent transnational law-enforcement cooperation. Pinkerton files, military service records, police memoirs and newspaper reports, including exposés with Barrie's own self-rationalizations, are used to reevaluate his early life and criminal career.Footnote ¹⁹ These critiques are informed also by recent studies of organized crime and “travelling criminals,”Footnote ²⁰ and criminological definitions of mobility centred on the distances travelled by offenders to engage in illegal activities.Footnote ²¹ The article follows many of Barrie's “journeys to crime”: the physical journeys from Australia to England, across the Atlantic and throughout North America; Barrie's skills development and widening criminal experience; the associational journeys with Prohibition- and Depression-era gangs and syndicates, and with Arnold Rothstein, Nate Raymond and other lesser known gamblers and fixers; and Barrie's increasing celebrity recognition and criminal status conferred through PNDA investigations and by sympathetic journalists.

Frequently described as the “Englishman” or “Britisher,” Peter Christian Barrie was born in Edinburgh, Scotland, on 14 February 1888, then migrated to Australia prior to World War I.Footnote ²² When he enlisted at Sydney in September 1914, his occupation was veterinary dentist and farrier, illustrating (if true) that he already had crucial competencies for horse substitution.Footnote ²³ Trooper P. C. Barrie, a motor driver and engineer in the 6th Light Horse Regiment, Australian Imperial Force, was deployed to Gallipoli with the Mediterranean Expeditionary Force. He suffered recurring bouts of dysentery and septic foot at Anzac Cove between May and August 1915, then spent six weeks on HMT Caledonian bound for England. He received further treatment at military hospitals in Lewisham and Harefield for concussion, sustained from an exploding shell over the troop transit, and dysentery. We can speculate that these experiences shaped Barrie's postwar attitudes toward authority and risk, his inability to settle in one place, and thus his evolving criminal identity. He was honourably discharged on 19 June 1916 as “being permanently unfit for active service,” but was classed as fit for home service and had secured employment at a London munitions factory.Footnote ²⁴ Therefore, by the mid-1910s, Barrie had already crossed several geographic borders, and illicit mobility quickly replaced patriotic mobility following his return to civilian life in England.

Barrie was arrested for several theft and fraud offences, including cheque book theft in March 1917, for which he served two months at hard labour, and “obtaining £275 by means of worthless cheques” in 1919, but he was discharged by Marylebone Police Court on that occasion.Footnote ²⁵ In September 1920 he was described as a Hampstead-based horse owner and amateur jockey, and was one of six defendants on trial at the Old Bailey for a series of horse sale and racing frauds. Barrie pled guilty to five offences, including falsely winning over £167 at the Faceby Plate at Stockton in October 1919 by substituting three-year-old Jazz for two-year-old Coat of Mail, running Homs as Golden Plate at Chester in May 1920, and entering an imaginary horse called Silver Badge at Cheltenham in December 1919 but actually racing Shining More. He was sentenced to three years’ penal servitude and served eight months at Dartmoor Prison.Footnote ²⁶

Barrie's release coincided with the “racecourse wars,” which Heather Shore has critiqued as a series of violent conflicts, involving “mainly metropolitan criminals in affrays and fights on the streets of London and on the racecourses of South-East England,” and to control bookmaking and track protection. As violence escalated from summer 1922 so did police and press surveillance of English tracks.Footnote ²⁷ Across the Atlantic, racing and racetracks were enjoying a remarkable resurgence after a period of severe restrictions. In the late nineteenth century, a strong anti-racing coalition of evangelical Protestants, social-purity and vice reformers and other progressives mobilized political allies to outlaw gambling and close tracks. Only twenty-five of 314 Gilded Age racetracks remained open in 1908. Racing ceased completely in New York between 1910 and 1912 and almost completely in Chicago between 1905 and 1922.Footnote ²⁸ However, the waning power of social-purity progressives, the popularity of card games with troops and greater tolerance of wartime betting, and the rise of a mass-production, mass-consumption economy with increased leisure time all helped transform the fortunes of the racing business. During the 1920s and 1930s thoroughbred horse racing was a highly lucrative mass spectator sport on both sides of the Atlantic.Footnote ²⁹

Despite having a passport limited to European travel, Barrie sailed for Canada in 1923, and became part of a vibrant interwar criminal Atlantic.Footnote ³⁰ He emigrated to North America to profit from racetrack corruption in the same period that American and Canadian entrepreneurs cultivated European markets for financial frauds and lucrative supply routes for liquor, narcotics and people. Within months of his arrival in Canada, Barrie claimed, “One night [I] simply walked across the border into the United States.”Footnote ³¹ More robust border enforcement and immigration controls were enacted by US and Canadian governments in the early 1920s, and supplemented existing Chinese exclusion laws. Yet restrictions were undermined by “elected officials on both sides of the border, corrupt police officers, and compliant railroad employees,” while smuggling gangs, document forgers and safe houses were found in all border communities. Astute operators could take advantage of busy border checkpoints, at Niagara and Buffalo for example, where thousands of legitimate workers crossed every day.Footnote ³²

Canadian immigration historians highlight the privileged status of British emigrants while Mae Ngai has emphasized the racialization of US immigration in the new post-1921 era of “numerical restrictions.” Power asymmetries rested on the dissociation of white Europeans and Canadians “from the real and imagined category of illegal alien” and a conscious decriminalization of certain types of white immigrants.Footnote ³³ Deportable criminal offences were narrowly defined, judges retained discretion when considering deportation applications, and the immigration quota enforcement bureaucracy was still evolving in the 1920s and early 1930s.Footnote ³⁴ No laws can ever be completely effective, but Barrie was a foreign felon without a valid passport who crossed both the Canadian–US and Mexican–US borders multiple times between 1923 and 1934.Footnote ³⁵ Further, he was arrested for several frauds, generally related to the sale of horses, in Winnipeg, Manitoba, Baltimore, Maryland and Mechanicsville, New York from the mid-1920s, but prosecutions were not followed up and he quickly moved on.Footnote ³⁶

Over the next ten years, Barrie travelled extensively throughout the United States, Canada and northern Mexico. Skilled travelling criminals such as professional thieves, prostitutes, gamblers and confidence men and women used multiple aliases to evade police surveillance and arrest warrants for a range of fraud and deception offences. The physical journeys to crime of one itinerant but relatively disciplined cohort and their criminal agency – unconstrained by national borders, jurisdictional boundaries or immigration restrictions – were regulated by the racing calendar.Footnote ³⁷ David Johnson identified professional gamblers associated with horse racing as leaders in the development of late nineteenth-century “intercity criminal networks and syndicates.”Footnote ³⁸ By the 1920s, travelling criminals could ally with urban syndicates for services and protection, which in turn extended the geographic, social and economic spaces through which they could safely travel. However, Barrie's distinctive doping and painting skill set and the high financial returns they could generate ensured that he was more intricately tied to premier racetracks than other con men and women.

A Pinkerton task force moved from track to track during the racing calendar in tandem with the professional criminals. Pinkertons had been policing American racetracks since the 1880s, providing gatemen, ushers and night watchmen, and monitoring crowds and traffic, as well as pursuing pickpockets, fraudsters, touts and prostitutes who worked the crowds on race day and in nearby entertainment districts.Footnote ³⁹ Scholarly focus has centred on the PNDA's controversial union infiltration, strikebreaking and labour espionage activities from the 1890s to the 1930s, but the agency continued to lead interstate robbery and fraud investigations, and to break up gangs of jewel thieves with the New York Police Department in the 1930s.Footnote ⁴⁰ Racetrack security remained core business throughout the interwar years during a period of considerable industry expansion. The racetrack squad undertook surveillance to “police and protect” the paddock and stables while webs of informants helped PNDA operatives monitor the grooms, exercise boys and jockeys, as well as race-day crowds. Pinkerton superintendent Clovis E. Duhain oversaw racetrack operations and Thomas Finnerty was the main PNDA operative at Havre de Grace. These men also made it their business to recognize the horses, trainers and owners.Footnote ⁴¹

Traditional narratives of crime and punishment during the interwar years are dominated first by celebrity bootleggers and gangsters, and then by bandits, bank robbers and public enemies during the New Deal war on crime. There is a voluminous literature on the criminogenic impacts of Prohibition which details the violent pooling of resources, consolidation of territories and markets, cartelization of illicit manufacturing, and formation of larger gangs and metropolitan and regional syndicates led by hypermasculine “big shots.” Studies of Detroit, Chicago and New York demonstrate that gangs and syndicates demanded fealty and discipline and, like pre-1920s vice lords, were enmeshed in complicated webs of political, police and judicial corruption.Footnote ⁴² Recent innovative studies of African American-controlled policy and numbers gambling in interwar Harlem, Chicago's inter-gang violence, and local bootlegging provide broader and more nuanced critiques of organized criminal activities in the interwar United States.Footnote ⁴³ Organized-crime groups were structurally diverse and multilayered, and could be simultaneously hierarchical, insular, fluid and decentralized. They varied in size and success. They easily incorporated different entrepreneurs such as lone female gun molls and larcenists, mobile con games, and the violent male enforcers and extortionists employed by more rigid urban crime syndicates.Footnote ⁴⁴

Barrie was a seasoned fraudster and con man. At times, he doped horses and provided ringers on a fee basis for betting rings and individual high-stakes gamblers; at other times he operated independently or in a smaller gang on the fringes of larger syndicates. John Kobler identified several men who operated on the fringes of Chicago gangs, including “lock picker, safecracker, and escape artist” Morris “Red” Rudensky.Footnote ⁴⁵ There was significant operational and jurisdictional overlap between lone operators, smaller gangs and hierarchical oath-bound “families,” as safecrackers, thieves and bank robbers utilized fences, safe houses and bail bondsmen protected by larger criminal gangs or dominant individuals. By the mid-1920s, Arnold Rothstein's bail bond business was one of the largest in New York City, and Barrie's connection to Rothstein is discussed below.Footnote ⁴⁶ Barrie was allied with Detroit's Purple Gang and with Minneapolis gangs, but, for over a decade, “New York crooks” provided financial backing for his frauds and expected to profit handsomely from the ringers painted by this immigrant specialist.Footnote ⁴⁷

By 1925, Barrie was in the greater New York area, working as a stable hand and then chauffeur for Samuel C. “Sam” Hildreth, a leading thoroughbred owner and trainer, employed by August Belmont in the 1910s, and from 1921 at the Rancocas Stable owned by oil baron Harry F. Sinclair (later implicated in the Teapot Dome scandal).Footnote ⁴⁸ Barrie later claimed he was paid by Detroit's Purple Gang to infiltrate Hildreth's operation and steal his doping mixture.Footnote ⁴⁹ Hildreth was also a long-time friend and gambling associate of Arnold Rothstein, whose spectacular turf, ring and ballpark winnings were often attributed to fixes. Rothstein's biographer surmised that they “had been partners in some of the biggest betting coups ever made in the history of racing.”Footnote ⁵⁰ There is no PNDA or newspaper evidence directly linking Barrie to Rothstein, a bookmaker, gambler, bail bondsman and narcotics kingpin, but it seems very likely that the ambitious fraudster and New York's master crook were involved in mutually beneficial betting schemes. It is also difficult to envisage Barrie's ringers competing at major northeastern or mid-western racetracks between 1925 and 1928 without Rothstein's knowledge or patronage, not least because of Rothstein's extensive network of racetrack informants and control over layoff betting.Footnote ⁵¹ Further, by 1926, Barrie had left Hildreth's employment and had enough money to legitimately purchase several racehorses and to set up his own riding stable.Footnote ⁵² As Katcher notes, “Rothstein's main function was organization. He provided money and manpower and protection. He arranged corruption – for a price. And, if things went wrong, Rothstein was ready to provide bail and attorneys.”Footnote ⁵³

Racetracks had long been important sites of upperworld–underworld intersection. Legitimate financiers and consumers mingled with professional gamblers, pickpockets and swindlers at the tracks. Wealthy bookmakers invested in stables and controlled jockeys. Legitimate and gangster investors partnered to finance racetracks (Rothstein and August Belmont II were the original investor–owners of Havre de Grace in 1912) and bright-light entertainment districts such as Saratoga's Lido Venice-Piping Rock strip.Footnote ⁵⁴ Many individuals moved easily between these worlds.Footnote ⁵⁵ Thoroughbred ownership was important to industrialists and bankers keen to flaunt their wealth and to status-conscious gangsters like the Capones. From 1931 to 1941, New York bootlegger William Vincent “Big Bill” Dwyer owned a large stake in Florida's Tropical Park, whose refurbishment was financed by Canadian bootleggers.Footnote ⁵⁶ Several Hollywood moguls and celebrities also became “turf moguls” through their ownership of racehorses and track investments.Footnote ⁵⁷ Prohibition and the illegal liquor trades extended old associations and created new alliances between legitimate financiers, syndicates, urban political machines and police.

In the years after World War I, crowds flocked to premier tracks to watch elite thoroughbreds compete for huge purses at Saratoga, Belmont and Havre de Grace, and to local short-distance tracks – often part of a network of carnivals and travelling fairs – as at Butte, Montana, to see bottom-level thoroughbreds and quarter horses vie for small purses.Footnote ⁵⁸ Changing attitudes toward competitive sports, decreasing working hours, increased leisure time and rising consumer confidence in the mid-1920s, as well as the aesthetics of the race-day experience, enticed Americans of differing backgrounds and classes. As Alison Goodrum observes, “Spectators went along to the races … to view the horseflesh and to take in the intoxicating atmosphere: they gambled, socialized and were entertained.”Footnote ⁵⁹ Crowd-pulling horses included Man O’ War in 1919–20, Gallant Fox in 1930, and rivals Seabiscuit and War Admiral (both Man O’ War descendants) in the second half of the 1930s.Footnote ⁶⁰

Racing historian Steven Reiss notes the “number of tracks in operation rose to 34 in 1929, of which 70% were new,” and there was a 60 per cent rise in the number of races, a doubling of the number of registered thoroughbreds, and purses “quadrupled to $13.9 million between 1918 and 1926.”Footnote ⁶¹ Florida, an expanding tourist destination and much-advertised tropical paradise, was home to four major tracks by the mid-1920s. Winter racing, traditionally limited to Havana's Oriental Park, greatly aided the recovery of Florida's tracks after the 1926 land-boom collapse.Footnote ⁶² Hialeah, north of Miami, was integral to Joseph E. Widener's triangular Kentucky–New York–Florida racetrack empire (East Coast society elites would spend August in Saratoga then winter in south Florida), and its 1931 redevelopment included elegant art deco styling, lush landscaping and imported flamingos.Footnote ⁶³ Three new racetracks opened in Chicago in the late 1920s: Washington Park, Lincoln Fields and Arlington Park, followed by Capone's local track at Hawthorne in 1931.Footnote ⁶⁴ A $2 million thoroughbred track opened in December 1929 at the opulent Agua Caliente resort near Tijuana, the centre of a booming cross-border liquor and gambling economy.Footnote ⁶⁵

Ashforth uncovered few details about Barrie's frauds between 1928 and 1931, yet the combination of new racetracks, extended seasons and fat purses undoubtedly increased underworld demand for Barrie's skills.Footnote ⁶⁶ He was therefore most likely hidden in plain sight and simply not yet under PNDA surveillance in these years. His white skin and dapper appearance also facilitated his movement through racetrack crowds, and ensured he was one of many well-dressed white men at the paddock or near the stables. Spectators at all the major racetracks in the South were segregated by law, and often by custom at northern tracks. Black horsemen had dominated American tracks after the Civil War but were edged out from the 1890s. Lower-status “negro clockers” and stable hands were still employed at many tracks but there were far fewer black jockeys and black trainers by the Jim Crow 1910s and 1920s. It is also noteworthy that in a period when criminality, mobility and detection were intrinsically linked to race, class and gender, African Americans feature in PNDA files on Barrie as chauffeurs, stable hands, trainers and racetrack clockers, and as unwitting rather than full accomplices.Footnote ⁶⁷

Technological innovations were transforming the race-day experience at premier tracks: public announcement systems appeared in the early 1920s and steel-frame electric starting gates debuted in California in 1929. The electrical totalizer, a giant board on the infield, recorded the amount of money wagered on each horse, the odds, the total pool and the mutual payouts. “A bet placed with any clerk at any ticket-selling machine was instantly and automatically entered into the pool, which allowed quick calculation of pre-race odds and post-race payouts” and so replaced preprinted slips and the fervent manual calculations that had to be updated every five to ten minutes.Footnote ⁶⁸ Investment in the totalizer was part of a major push by racetrack owners and investors to eradicate illegal wagering and race fixing and thus to clean up the sport, as gambling reemerged as an important income stream for organized crime during the last years of Prohibition as racetracks and races increased. Syndicate-backed Moe Annenberg monopolized the racing-news wire service and the dissemination of racing results from 1927, but organized con men had made money from advance knowledge of racing results for several decades.Footnote ⁶⁹

Purses and gate receipts dipped significantly in the early Depression years. Vacation resort operators pushed for pari-mutuel wagering on dogs and horses to increase footfall and to eradicate the protection rackets controlling trackside bookmaking.Footnote ⁷⁰ Hialeah's owner Joseph Widener lobbied hard for pari-mutuels to be introduced in Florida in the face of strong opposition from Cuban racetrack owners and southern Baptists. A pari-mutuel bill was defeated in 1929, stirred a bitter legislative fight two years later, and was passed over the governor's veto in June 1931. The state's first legal pari-mutuel horse race took place at Tropical Park on Boxing Day 1931, and over the next twelve months Florida's three tracks produced $710,388 in pari-mutuel tax revenue. By 1933, ten states had adopted pari-mutuel betting, which became an economic lifeline for many cash-strapped governments.Footnote ⁷¹ However, betting rings could subvert pari-mutuels through comeback bets, namely money placed on bets at poolrooms and bookmakers across the United States and then wired into the betting bureaux at the tracks.Footnote ⁷²

When Shem–Aknahton trounced Byzantine in October 1931, there were immediate suspicions of foul play. The fraud was exposed by Morning Telegraph journalist John J. “Fitz” FitzGerald, who asked the obvious question: how could the form of a horse valued at under five hundred dollars only a few days before the race have improved so dramatically to draw wagers of $20,000 from across the country?Footnote ⁷³ Shem–Aknahton's sensational win allegedly earned over a million dollars in total for Barrie, his immediate associates, and wider betting rings in on the know, but “then the wise guys couldn't keep their mouths shut … and the bubble burst.”Footnote ⁷⁴ When Shem's trainer was instructed by officials to have the horse ready for inspection on 4 October, both had disappeared.Footnote ⁷⁵

The American Jockey Club was established in 1894 to protect horse racing “from the sharks of the track and betting rings.” It set the racing schedule and rules, maintained lists of thoroughbred horses and their pedigrees, and had the power to licence trainers and jockeys. Early twentieth-century crackdowns on race fixing led many states to create racing commissions to oversee track licences and personnel at the local level, allocate race dates, and hear grievances. Those violating the rules or caught cheating could have their licences revoked, which could have a devastating effect on livelihoods, especially if they were banned from all tracks in that state.Footnote ⁷⁶ Within days of the Shem–Aknahton fraud, the gang and their horses were ruled off the turf by the Maryland Racing Commission. It would take several more weeks for members’ identities to be confirmed by PNDA investigators: A. Ray alias Nate Raymond, Leo Kammerman alias Leo Canerman, Peter Westley alias Patrick Christie (Barrie), Arthur Kennedy, William Marino (listed as Shem's owner), J. LeBolt alias Julius DeLott, Herman “Blackie” Brackenheimer and Vladmar Sulick.Footnote ⁷⁷ Kennedy was a legitimate trainer; the rest were not. Aside from Barrie, the main betting-ring men were William J. “Big Bill” Duffy and Nathaniel “Nigger Nate” Raymond, identified as being together at Havre de Grace on 3 October.

Ex-con Duffy was a well-known restauranteur and boxing promoter on Broadway, a nocturnal bright-light city space full of “chorines, hoofers, promoters, publicity agents, speakeasy hostesses, [and] rum runners,” gamblers and New York City mobsters, as well as legitimate businesses.Footnote ⁷⁸ Raymond, a “Forger–Confidence Man–Gambler,” originally from San Francisco, was a professional high-stakes gambler, had been barred from Pacific Coast League parks for fixing baseball games, and was one of the eight players at Rothstein's infamous last card game in Manhattan. Rothstein still owed him over $303,000 when he was assassinated and Raymond was briefly arrested as a material witness to Rothstein's murder in November 1928.Footnote ⁷⁹ Despite the racially pejorative description, Raymond was not African American, but a white male with “a swarthy complexion.” He was Jewish and had attended Rothstein's levaya.Footnote ⁸⁰ Raymond was probably Barrie's main turf-fraud partner between 1928 and 1931, and Barrie might therefore have been active on the West Coast during the period when Ashforth could not locate him.Footnote ⁸¹ Further, while on the East Coast, Raymond was domiciled in Long Island and Steve Maby, Barrie's former trainer turned PNDA informant, told Fitz that Barrie's headquarters in the late 1920s and early 1930s was near the Long Island racecourses.Footnote ⁸²

From 4 October, thoroughbreds Aknahton and Ep were transported to New York and then Lake County Fairgrounds at Crown Point, Indiana, using a circuitous route and alternating van and rail, before Ep was abandoned and Aknahton was transported to Agua Caliente via Bowie, Maryland, where he raced as Hickey in late November 1931. Shem was later moved to New Jersey. Pinkertons investigated rail and stock yards, urban stables and garages; attempted to photograph horses at Crown Point (Aknahton) and Jersey City stockyards (Shem); interviewed witnesses and informants; visited hotels and businesses; and checked phone records to track gang members and build a timeline of their movements. Horses had been shipped by Barrie, Raymond and Canerman using different aliases but were eventually tracked through the horse health certificates required by railroad companies.Footnote ⁸³ Between October 1931 and February 1932, the Pinkertons exercised a multiagency approach for a complex case underpinned by extensive geographic mobility and hindered by men using multiple aliases and imperfect horse descriptions. They worked with local police in New York, Baltimore and Chicago, and with the US Immigration Service as a plan to apprehend and deport Barrie as an undesirable alien began to take shape.Footnote ⁸⁴

Incomplete PNDA intelligence suggested that the betting ring was planning another horse substitution at a winter track and the gang's base of operations was either Tijuana or Havana. The major operatives were tied to New York–Long Island while Barrie worked out of a mobile horse van or his distinctive black Lincoln touring car with red wheels. In early January 1932, “Blackie” Brackenheimer (former manager of boxer Max Schmeling's camp), Bill Duffy and Larry Fay (New York bootlegger and racketeer) were spotted vacationing in Daytona, Florida, and asked to leave Tropical Park by stewards acting on advice from PNDA superintendent Duhain. Both Tropical Park and Hialeah were under PNDA surveillance when Willis Kane (Barrie), recently arrived from Tijuana, attempted to stable five horses at Tropical Park in early February. Kane and the horses were directed to Hialeah.Footnote ⁸⁵

Hialeah officials became suspicious on 23 February when large comeback bets were placed on bay-coloured Gailmont. Around $7,000 of the $8,907 wagered was wired to the track shortly before the race commenced and recorded by the recently installed totalizer. The race for three-year-olds went ahead, but after a false start Gailmont “broke down and finished the last quarter on three legs, a hopeless cripple.” Pinkertons impounded the horse when he reached the paddock.Footnote ⁸⁶ Track officials determined that Gailmont was dyed four-year-old Aknahton carrying a racing injury sustained at Agua Caliente six weeks earlier. The fraud would have been very apparent if the horses had been closely examined: the real Gailmont was a gelding but the horse that raced at Agua Caliente and Hialeah in early 1932 had not been castrated. The application of “hefty blocks of ice” to Aknahton's genitals was used at Havre de Grace and this method could have been repeated elsewhere.Footnote ⁸⁷ The Gailmont substitution exposed Aknahton as a five-time ringer and precipitated a dramatic unravelling of Barrie's fraud operations. Needless to say, the case was referred to the Miami Jockey Club. Its decision to rule two owners and a trainer, Kane, John P. Crawford and A. F. Tavener, off the turf along with their five horses was confirmed by the newly empowered Florida State Racing Commission.Footnote ⁸⁸ But Kane (Barrie) – still known to Pinkertons as “Patrick Christie” – had again disappeared.

Pinkerton and local Miami police surveillance culminated in Barrie's arrest when he collected his distinctive automobile from a local garage. He was interviewed by US immigration officers in Miami city jail on 1 March, posted five hundred dollars bail and lodged at a downtown hotel to await the deportation warrant (illegal aliens without criminal records could deport voluntarily). As Pinkertons congratulated themselves, Barrie jumped bail on 13 March.Footnote ⁸⁹ McGarry later triumphantly declared that the “turf swindler and international crook … has left the country for parts unknown.”Footnote ⁹⁰ Aknahton had gone too. Their whereabouts were known to associates in major northeastern and mid-western cities, who continued to utilize Barrie's services.Footnote ⁹¹ W. E. Fred (Barrie) and a previously unreported female accomplice, “Mrs. Jean Browning,” aka Ethel Patricia von Gretchen, were linked to ringers at Saratoga, Belmont, Fort Erie and Jamaica in 1932. Voltagreen ran as Janie G at Fort Erie, Ontario, on 6 August, while Regula Baddun ran as Saintlite at New York's Jamaica track on 3 October, exactly one year after the Havre de Grace coup. Fred and Browning were swiftly ruled off the turf at both tracks, but the bets had already been paid out.Footnote ⁹²

While a fugitive from the Pinkertons and the US Immigration Service, Barrie sold his story to the New York Daily News and provided material for a twelve-part “glowing, colorful yarn of intrigue, fraud and swindle on the racetracks” in November and December 1932.Footnote ⁹³ The articles were framed as both salacious exposés and quasi-public-service announcements, as well as acts of desperation by a penniless crook. Racing journalists such as Bob McGarry and Paul Gallico had long marvelled at Barrie's brazenness and frequently adopted lighthearted prose to describe the daring exploits of a likeable rogue. The story of the clever master ringer who fooled jockey clubs and racing officials is repeated in many racing histories and retold in online popular-history podcasts.Footnote ⁹⁴

Alternative characterizations of Barrie as a calculating con man who mutilated horses; deliberately included guiltless, albeit naive, jockeys and trainers in his frauds; and extorted journalists were hinted at but rarely discussed in detail. Further, the New York Daily News articles were hardly repentance-based confessions. “I never had any compunction about ringing a horse,” Barrie declared. “Certainly it was crooked. The game is full of thieves. I was cheating cheaters.”Footnote ⁹⁵ His ringers were still running; he had sufficient funds to purchase thoroughbreds and to stable, feed and transport them; while he and his accomplice paid for numerous hotels in cash as they moved between tracks in 1932–34.Footnote ⁹⁶ The articles can also be read as bold advertisements of Barrie's skills and successes and that he was still in business, touting for patrons now that Raymond was serving time in Sing Sing Prison in upstate New York. One PNDA source noted that Barrie's associates were “sore” at the newspaper interviews.Footnote ⁹⁷ However, the information he gave up was selective: most of the named associates were either dead or in prison, the list of ringers was incomplete, and he did not volunteer information about the period from winter 1928 to spring 1931, or his whereabouts after he left Miami in mid-March 1932. And, if criminal associates were really “sore” at Barrie, then the frustration of a major betting ring by Gailmont's eleventh place in February 1932 was significant.

Throughout 1933, Pinkertons were conducting surveillance on a blonde woman in her twenties in the New York–Long Island area and at Virginia tracks. Both Barrie and von Gretchen used different aliases when buying and selling horses and at hotels and racetracks, which continued to slow PNDA enquiries. In autumn 1933, both were seen at Laurel and Bowie racetracks in Maryland, but it is not clear whether there were suspicions of doping or substitution in specific races.Footnote ⁹⁸ Barrie's photograph and a list of eleven aliases were circulated to all PNDA offices in early January 1934.Footnote ⁹⁹ By this time, Barrie was a well-known figure at many US and Canadian racetracks and the deliberate use of a lesser-known accomplice could have been a deflective tactic. The likelihood that Barrie was now operating semi-independently on the fringes of organized crime networks might also have made syndicate silence and protection less secure. Pinkerton operatives could not agree whether there was any romantic attachment between Barrie, then forty-five years old, and this much younger woman, but they were certainly entranced by the tall good-looking von Gretchen. Witnesses also found her to be much more memorable than Barrie.Footnote ¹⁰⁰

Mrs. Helen Lewis's (von Gretchen) request to a groom at Saratoga Springs in August 1934 to transfer three-year-old colt Easy Sailing from one stall to another prompted the suspicious groom to alert the Pinkertons.Footnote ¹⁰¹ Two painted thoroughbreds, recent arrivals from Fort Erie, had already been spotted in a nearby farmer's field, thus Saratoga was being watched closely.Footnote ¹⁰² Pinkertons tailed Lewis, who led them straight to Barrie, “sitting behind the wheel of a horse van, about to drive a nag away.” Barrie and three associates were arrested by Pinkertons and Saratoga police and charged with grand larceny, although it was clear from the outset that this was merely a holding tactic to enable US immigration officers to organize Barrie's deportation, as his associates were quickly released.Footnote ¹⁰³

By the early 1930s, Barrie's de-territorialized mobility and his continuous journeys to crime directly challenged federal social- and crime-control policies in a period of rising crime, violence and insecurity. Both the Hoover and Roosevelt administrations adopted more aggressive post-entry social-control deportation policies amid increased public anxieties over unemployment and lawbreaking, public weariness with the failures of Prohibition, and political denunciations of foreign gangsters and native-born bandits.Footnote ¹⁰⁴ One 1930 editorial declared, “Aliens who are taking advantage of America's hospitality to carry on rackets of every sort deserve no consideration or mercy. They ought to be sent back to their native countries and denied the privileges of ever entering the United States again.”Footnote ¹⁰⁵ Criminal deportations increased from 1932. Nevertheless, painting a horse to take the place of another was not actually a criminal offence in either Maryland or Florida, and conspiracy to commit fraud and false pretences were not extradictable offences between the US and Canada.Footnote ¹⁰⁶ Barrie does not appear to have been convicted of any crimes during the ten years he spent in North America but he admitted to the US district attorney at Saratoga that he had entered the US illegally and had no permanent address, while his numerous frauds were discussed in his newspaper articles.Footnote ¹⁰⁷ As a non-domiciled immigrant with “no fixed address” he was particularly vulnerable to charges of vagrancy and becoming a public charge.Footnote ¹⁰⁸ In November 1934, three months after his arrest at Saratoga, Barrie left Ellis Island on the SS Caledonia bound for England.Footnote ¹⁰⁹

There was mixed journalistic reaction to Barrie's deportation. Drawing on broader cultural rankings of lesser and more serious illicit activities which evolved during the Prohibition years, his allies noted that Barrie was a crook, but opined that the real crooks were the gamblers who profited from the fraudster's ringers rather than the horse painter himself. One New York Daily News writer dismissed Barrie as “a specialist who could be trusted by the gangsters” but not a big shot: “Barrie was merely a small-time artist used as a tool by gamblers.”Footnote ¹¹⁰ Further, criminology studies of mobility and criminal achievement have emphasized the relatively short distances travelled by drug, market and property offenders between their place of residence and any crime location, although there are obvious exceptions such as serial sex offenders and interstate serial killers. They also highlight the importance of financial returns and criminal networks in shaping an offender's mobility, as well as age, as older higher-rate offenders with a wider geographic reach and more criminal contacts were higher earners.Footnote ¹¹¹ Barrie's case study challenges the press dismissals of his significance and nuances the linkages between migratory entrepreneurs and criminal achievement.

Barrie was a talented minor player in complex illicit gambling markets and the racing economy. He was a professional con man and racketeering specialist operating for, or on the fringes of, larger syndicates through a series of shifting alliances and associational networks. By 1933, Barrie's big-shot associates were dead or in prison while his career was defined by survival, adaptability and longevity. The “Perfect Villain of Horse Track” was very much alive with a transferrable and profitable skill set that was still in demand. It is impossible to calculate the exact amount of illegal winnings from Barrie's ringers and he never corrected the figures proffered by McGarry and other journalists. Despite his frequent pleas of poverty – particularly to sympathetic journalists – ringing horses must have brought significant financial returns, otherwise Barrie would not have opted to remain in North America for ten years.Footnote ¹¹²

He was an experienced middle-aged peripatetic offender whose purposive mobility and multiple aliases helped avoid detection and apprehension for a relatively long period. And, in the early 1930s, the Pinkerton National Detective Agency deployed large numbers of agents at considerable expense to go after this gambler's “tool.” The agency's reputation as the nation's most powerful single law-enforcement body was being challenged by the rising profiles of federal law-enforcement agencies, particularly J. Edgar Hoover's Bureau of Investigation and Harry J. Anslinger's Federal Bureau of Narcotics, and the PNDA business model was changing with greater emphasis on security and private protection contracts. Yet the Pinkertons’ pursuit of Barrie, whether a small-time artist or not, enabled operatives to showcase their criminal-investigation, detection and crime-fighting skills in the United States and the effective use of the PNDA's network of overseas offices.

Nevertheless, by November 1934, it was probably time for Barrie's North American career to end. He had been ruled off the turf in Canada, Maryland, Florida and New York. His ability to operate at the tracks with the highest purses and most lucrative betting was increasingly constrained both by his celebrity and by the Pinkertons. The gradual adoption of horse saliva testing for drugs, the tattooing of an identification number on a horse's upper lip, and photographing of a horse's unique “nighteyes” (calluses on the inner side of each leg), as well as ostensibly stricter monitoring of horses and personnel at major tracks, made it easier to expose ringers.Footnote ¹¹³

Viewed against the backdrop of increasing political and public hostility to foreign offenders, Barrie was the consummate and remorseless alien habitual criminal who had deliberately undermined the “sport of kings” by taking advantage of America's hospitality to profit handsomely from racetrack racketeering. His physical removal from the United States could be portrayed as a small but notable victory during one phase of a much longer war on illegal wagering and race fixing in the United States. In 1934, a career unfettered by national borders was at last curtailed by the host nation's immigration laws. However, criminal deportation was an administrative tool rather than a strategy for reformation or desistance. Barrie's North American exploits undoubtedly conferred status, success and criminal reputation: despite his ignominious return to England, he was still the master painter and the clever fraudster who had outwitted jockey clubs, racetrack owners and trainers across the US, Canada and Mexico, and had eluded the famous Pinkertons for a considerable period of time. Further, Barrie's forced return led to a timely career relaunch and at least twenty more years of doping, dyeing and ringing horses at major British tracks.Footnote ¹¹⁴