In 1963, two British criminals masterminded the robbery of 2.6 million pounds in cash from a Royal Mail Train, an amount worth 45 million pounds today. The robbery and its aftermath caused a nationwide sensation.
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In 1963, two British criminals masterminded the robbery of 2.6 million pounds in cash from a Royal Mail Train, an amount worth 45 million pounds today. The robbery and its aftermath caused a nationwide sensation.
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The books used to compose this podcast included:
“The Great Train Robbery: Crime of the Century,” by Nick Russell-Pavier and Stewart Richards, and,
“The Great Train Robbery: Fiftieth Anniversary,” by Bruce Reynolds and Ronnie Biggs
Music used in this podcast included:
Part One intro, Part Two outro: “Too Late Now,” by Go By Ocean/Ryan McCaffery
Part One outro and Part Two intro: “Los Encinos,” by Quinoas Moreira
Long before Claus Von Bulow or OJ Simpson, in 1924, two Chicago teenagers committed what was called at the time, “The Crime of the Century,” only to be spared by the efforts of the greatest defense attorney in American history.
During their scouring of the Wolf Lake area, police detectives questioned the game warden of the forest preserve that was located nearby about any recurring visitors to the location. One of the names he revealed was that of Nathan Leopold, Jr a nineteen year old ornithologist and recent Phi Beta Kappa graduate of the University of Chicago, currently taking a class at the University of Chicago’s law school. On Sunday morning, May 25, two policeman were sent to Leopold’s home to pick up the teenager for questioning, the house coincidentally in the Kenwood section near both the Harvard School and Bobby Franks’ house. Leopold had plans for a date that Sunday and was initially resistant to coming down to the precinct, but the police assured him that their captain just wanted to ask some routine questions and if he brought his car he would be back in no time.
Once Richard Loeb’s name was mentioned he also was brought to the LaSalle, placed in a separate room and questioned until the early morning hours. He claimed he left Leopold around dinnertime and mentioned nothing about picking up girls, an obvious contradiction that was certainly suspicious. The next morning, Leopold and Loeb found themselves in custody, in separate police stations, Leopold at Crowe’s headquarters in the Criminal Courts Building, Loeb at a nearby precinct house.
At the Franks’ house, as the dinner hour approached, Bobby Franks’ parents began to wonder where their son was. Jacob and Flora Franks were the type of typically wealthy family that populated the Kenwood neighborhood. Jacob Franks’ wealth initially stemmed from a pawn shop he inherited from his parents known as Franks Collateral Loan Bank. Franks eventually diversified his business interests, first into separate watch and watch case manufacturing companies and then into various real estate and stock investments which generated a net worth of at least 1.5 million 1924 dollars, equivalent to about 27 million dollars today.
. Because of the incredible public and media interest generated by the death of Bobby Franks, the Franks family decided to hold a small, private funeral service in their home as opposed to what might become a public circus. The Franks family were converts to Christian Science from Judaism and the affair consisted of various readings and hymns before a police escort accompanied the Franks procession to Rosehill cemetery, the pallbearers all fellow students from the Harvard School.
Understanding his nephew’s predicament, Jacob Loeb decided to reach out to an even more prominent individual, Clarence Darrow. By 1924, Darrow was nearing the conclusion of one of the most illustrious and controversial legal careers in US history. Starting from a small law practice in the tiny Ohio town of Andover, Darrow eventually made his way to the city of Chicago where he became famous and frequently vilified for representing various labor officials like Eugene Debs and Big Bill Haywood. A 1911 scandal involving a Los Angeles bombing case which resulted in Darrow negotiating a plea deal and accusations of jury tampering via bribery alienated the attorney from organized labor. Darrow then switched to criminal and civil defense, mostly involving defendants facing the death penalty. In over 100 cases, Darrow had only one defendant executed and that was when he joined the defense only for the penalty phase of the trial. Despite a practically disheveled appearance, Darrow’s quick legal mind and remarkable eloquence during impassioned closing arguments made him the most famous trial lawyer in America.
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Long before Claus Von Bulow or OJ Simpson, in 1924, two Chicago teenagers committed what was called at the time, “The Crime of the Century,” only to be spared by the efforts of the greatest defense attorney in American history.
Clarence Darrow would not begin his summation until the afternoon of August 23rd, so anticipated throughout the city of Chicago that a mob descended on the courthouse hoping to push into the courtroom. This throng congregated in the stairwells, common areas and hallways leading to the sixth floor chamber where Darrow was scheduled to speak. Twice after the midday recess, the famed attorney attempted to begin his summation, only to stop, the noise of spectators emanating from the hallway outside of the court too boisterous, police and bailiffs struggling to push the crowd out of the courtroom’s proximity. Angrily, the judge contacted the city police chief directly, demanding that order be restored. Within minutes, additional police resorting to billy clubs eventually removed the source of this distraction.
Darrow immediately lived up to his reputation. Although he had formulated his strategy well in advance, he surprised the court, the media, the prosecution and even the defendants after a lengthy opening statement by pleading his clients guilty to both murder and kidnapping. Strategically, this was a brilliant maneuver on several fronts. It ambushed Crowe by not allowing the prosecutor to potentially get two bites of the apple in attempting to condemn the defendants. If he was aware of this strategy in advance, he would withdraw most likely the kidnapping charge and attempt to retry it later. Darrow’s plea circumvented that option. The decision as to what sentence the defendants received now was the sole responsibility of the judge, who would be asked to personally condemn two teenagers as opposed to a jury.
On the eleventh of September, 1924, Leopold and Loeb would begin serving hard time at Joliet state prison, a forbidding stone edifice housing some of Illinois’ most hardened criminals. One immediate hardship was the end of the meals that they were able to order from a Chicago restaurant during their trial. Although they granted interviews upon their entrance to the prison, Loeb would never publicly speak again and Leopold waited twenty years before interacting with a journalist. This despite repeated press attempts to provide updates on the successive anniversaries of their incarceration. Possibly to separate the two prisoners, Leopold was quickly transferred to Stateville prison, a brand new maximum security facility. The formerly high profile prisoners were so isolated that Leopold only found out about the 1929 death of his father from a prison employee.
Despite his recent parole rejection, Leopold cooperated with the Saturday Evening Post on an April, 1955, four part series that was sympathetic. Even more eventful was the 1956 novel Compulsion written by Meyer Levin, a runaway best seller that was a very thinly disguised account of the Loeb and Leopold murder and an eventual film starring Orson Welles. Once again, Nathan Leopold was an American celebrity, although he hated the book and sued Levin and 20th Century Fox for invasion of privacy, an unsuccessful suit that dragged on for most of the rest of his life. Perhaps, attempting to tell his side of the story, in 1958, Leopold published Life Plus 99 Years, a sanitized autobiography also undertaken to persuade any future parole proceedings. A best seller, the book created an additional groundswell for Leopold’s release. This sentiment finally played out on February 13, 1958 when Nathan Leopold emerged from Stateville Prison, a free man.
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The books used to compose this podcast included:
“Leopold and Loeb: The Crime of the Century,” by Hal Higdon, and
“Arrested Adolescence: The Secret Life of Nathan Leopold,” by Erik Rebain.
The music used in this podcast included:
Intro, Part One and Outro, Part Two: “Dance of the Gypsies,” by Hanu Dixit
Outro, Part One: “Never Surrender,” by Anno Domini Beats, and
Intro, Part Two: “Inconsciousness,” by Mini Vandals
The shocking story behind the biggest swindle in the history of Wall Street.
Agent Cacioppi was so taken aback by Madoff’s candor and unusual cooperation he called his office to determine what he should do next. Typically, a subject with Bernie’s sophistication and community stature would refuse to answer questions and stall, at least requesting time to speak with or even have an attorney present before answering any questions. Madoff’s admissions to the agents were an unexpected response. The agent was told to arrest Madoff and bring him to FBI offices at 26 Federal Plaza.
Upon graduation from college, Madoff briefly attended Brooklyn Law School but unlike his brother Peter, who graduated from Fordham Law School, he dropped out after a year. He did pass the requisite exams to not only sell financial securities but to also operate his own securities brokerage firm, which he formed in 1960, calling it Bernard L. Madoff Investment Securities. By then, Madoff was already married to Ruth Alpern, the daughter of a successful accountant, Saul Alpern. Another occasional fable that Madoff spun was that his working capital came from his summer jobs installing sprinklers and as a lifeguard. He frequently left out the fact that his father in law not only lent him fifty thousand dollars, he also gave him a desk in his firm’s office and referrals of all of Saul’s client base.
By the early seventies, several personal events greatly affected Madoff, the sudden and relatively early death of both of his parents and the inclusion of his brother Peter into his growing business entity. Between July 1972 and December 1974, Ralph and Sylvia would both die suddenly before their sixty-fifth birthdays an event that probably prompted the elder Bernie to take his younger brother under his business wing. Peter was a critical employee who became more operations and technology oriented, helping to keep the firm’s broker dealership on the cutting edge of upgraded technology in a securities market environment that was undergoing a technological revolution. And Peter would also assume the role of chief operations officer, a critical responsibility in any brokerage firm but even more so within Bernard L. Madoff investment securities.
His sons, Mark and Andrew, newly minted graduates of the University of Michigan and Wharton respectively were both now working for the firm, albeit on the broker dealer side of the business.
Avellino claimed that all of the money was there and was in the hands of his money manager, Bernard Madoff. As soon as he had heard of the SEC inquiry, Madoff tried to get ahead of what he knew was coming. Not only an SEC demand for the return of the assets but a possible scrutiny of his trading history to determine whether or not he in fact was running a legitimate money management firm, with ongoing investment in the markets. To do this he tasked one of his employees, Frank DiPascali, the individual who already was involved in producing investor statements that were most likely either distorted if not out right falsified, to reconstruct trades for all of the Avellino and Bienes accounts that would demonstrate the profits necessary to generate the claimed returns. These fictitious trades also had to stand up to SEC scrutiny. Amazingly, Madoff’s conversations concerning his trading strategies and DiPascali’s creation satisfied the SEC, however they did get a court order to force Madoff to return what were illicitly collected funds.
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The shocking story behind the biggest swindle in the history of Wall Street.
But, if many of Madoff’s clients were happy to not question his returns and process, the cynical, highly competitive and data driven world of Wall Street always invited scrutiny of its biggest stars, even if this was the result of envy or alienation. In Harry Markopolos, one found an individual motivated by both market place rejection and a competitively brilliant grasp of financial marketplace analytics. In 1999, Markopolos was employed as a portfolio manager by Rampart Investment Management, a small Boston, Massachusetts options trading shop that managed a modest amount of money. Markopolos was quite familiar with Bernie Madoff, his firm having marketed a split-strike conversion product that he helped develop. Unfortunately, the product did not generate particularly good returns and was eventually scrapped, Markopolos additionally both intrigued and frustrated by repeated stories of the phenomenal performance generated by Bernie Madoff. If you’re so smart, why the hell can’t you do what Bernie does? His hard boiled, Boston sales compatriots constantly needled him. To a quant like Harry Markopolos this was the ultimate put down and challenge, but there wasn’t much he could substantively do about it.
That changed when a senior co-worker named Frank Casey, returned from a New York sales call he had taken with Rene-Thierry Magon de la Villehuchet at Access International Advisers. Villehuchet not only managed money for some of Europe’s most high profile aristocrats he was literally a member of the French nobility himself. In his sixties, he was a client of Bernie Madoff’s since 1985, and rebuffed Casey’s sales pitch with glowing accounts of Madoff’s consistent high returns and reporting process that purported to send daily updates of all transactions performed on behalf of Access’s accounts. Casey then played the only sales card he had left, asking why Rene-Thierry allowed Madoff to hold the securities he purchased on Access’s behalf himself, as opposed to a third party custodian which was required for registered investment managers. Villehuchet’s answer was simple. Bernie Madoff wasn’t a registered money manager, so he was not required to do so and the Frenchman was dismissive of any of Casey’s concern, saying he trusted Madoff implicitly. The meeting quickly terminated with at least Villehuchet providing a copy of his returns and portfolio performance. Casey subsequently got seven years of such performance from Broyhill Securities’ All Weather Fund, another Madoff feeder fund and tossed this information on Markopolos’ desk.
This article was quickly followed up by another piece in the much more formidable business publication, Barrons, written by Erin Arvedlund. Again, although not accusatory, it was certainly skeptical of Madoff with similarly specific questions. Madoff’s response to these articles was to have Frank DiPascali construct a fake in-house computer terminal that supposedly was a trading platform connected to other trading counter parties, in fact it was connected to another employee’s in house terminal, hidden in another part of the office, all of these simulated trades completely bogus. Another DiPascali creation was a supposed live screen of an account at the Depository Trust and Clearing Corporation, known as the DTC, where securities owned by Madoff purchased during alleged trades were being held in his account. The fake reproduced the DTC’s logo, fonts, formats even the type of paper used for actual DTC reports.
On December 11, 2010, on the second anniversary of his father’s arrest, Mark Madoff committed suicide by hanging himself from his apartment ceiling with a dog leash. At the time of his death he was the subject of nine federal lawsuits, including suits brought by trustee Picard. His wife had already changed her and their childrens’ last name to Morgan. Unlike Andrew he seemed deeply sensitive to allegations that he knew about the fraud. His body was discovered by his stepfather in law when he rushed to the apartment after Mark’s wife received some alarming e-mails, Madoff’s 22 month old son and pet dog left alone in the apartment. This suicide, did not stop the relentless Picard, who then filed suits against Mark’s ex-wife and current spouse to recover funds deemed ill gotten gains.
Upon sentencing Bernie Madoff was sent to the Federal Correctional Institution at Butner, North Carolina. He occasionally granted interviews that were mostly self-serving with Madoff blaming his behavior on the culture of Wall Street or getting in over his head on something he never meant to pursue on a long term basis. He expressed exasperation with his clients who he labeled as greedy, especially the big four, three of whom were now dead. Although he continued to correspond with his wife, his two sons allegedly never spoke to him again, after he confessed his role in the fraud, one of few developments in his life that actually seemed to disturb him. Although initially accounts of him being assaulted in prison circulated in the media, he eventually referred to Butner as a relatively pleasant place akin to a college campus, his main objection to prison the sheer boredom it entailed.
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For twenty years, Whitey Bulger terrorized Boston with the full collusion of the FBI. On the run for sixteen years, he was eventually arrested on June 22, 2011.
Between the ages of thirteen and eighteen Bulger was arrested ten times, for crimes ranging from larceny, drunk in public and assault and battery. Only once were charges ever pursued to the point of a criminal conviction and even then, Whitey was able to get the charge reduced on appeal. It is no wonder that he developed an arrogant disdain for the criminal justice system and a sense of invulnerability. Unfortunately, this mentality only increased the severity of his transgressions. In May of 1948, Bulger and two accomplices enticed a young female into Whitey’s car and attempted to rape her at a beach in Dorchester. The girl fought back and was kicked to the curb, but not before getting the license plate. All three teens were quickly arrested. Again, Bulger plead guilty to a lesser assault charge, paid a fine and avoided a serious prison term. Within two months, he was arrested again, this time for a drunken assault in a diner that turned into a brawl with the police who showed up to arrest him. Again, he plead guilty to the lesser charge of public drunkenness, paid a modest fine and walked away.
Despite Bill Bulger’s vehement and relentless involvement, including an eleventh hour visit to DC to the Director’s office for an unscheduled, in person request for a last minute reprieve, on November 13, 1959, Whitey was flown commercial, with federal marshals, from Baltimore to San Francisco. From there, in leg irons, he was placed on the small ship that transported him to the center of San Francisco Bay and the Rock. This was an especially isolating development for Whitey for in the late fifties transcontinental flight was a luxury the Bulger family certainly could not afford. He would have to rely on letters only, the occasional visit from his brother or other family members now an impossibility.
On May 27, 1981. In broad daylight, at a country club in Tulsa, Martorano followed Roger Wheeler to his car in the parking lot and as Wheeler got in Martorano pulled the door open, put a bullet right between Wheeler’s eyes and hopped into a getaway car driven by another Winter Hill mobster. Tulsa investigators quickly determined that criminals from Boston were probably involved, but when they and Oklahoma City FBI agents contacted Boston FBI, they got nowhere.
Gradually, even the highest level coke and pot dealers were invited to the upstairs office of the Triple O’s Bar. There, Whitey would be waiting, usually with at least Kevin Weeks, a former bouncer that Whitey took under his wing, gradually relying on him as one of his top enforcers.
In July of 1956, there was no cushy Club Fed where Whitey could serve out his time in relative penal comfort. Instead, he was sent to the Federal Penitentiary in Atlanta, a huge, forbidding edifice that had housed the likes of Al Capone, Mickey Cohen and Vito Genovese. By comparison Whitey Bulger was a two-bit, bank robber, not exactly intimidating at 5’10”, 150 pounds and other than a few hoodlums back in Boston not particularly well connected. After thirty days of quarantine that was mandatory for every new inmate, Bulger was assigned to one of the eight man cells that comprised most of the tiers of the prison.
Although Bulger had shot some gangster rivals to death in his early battles with the Mullens, his hands on violence began to ramp up in the late seventies, probably as a result of his newfound power as the most powerful criminal in South Boston. This attitude was evidenced in the matter of Louie Latif, a bookmaker and drug dealer who began to behave erratically, first by murdering several business associates who caught him stealing and then by dealing cocaine. Both behaviors were not only repeatedly unsanctioned by Bulger, Litif also refused to pay rent. Summoned to the upstairs office at Triple O’s, Litif was pointedly warned that he was crossing a very serious line. Litif responded that as long as he and Whitey were friends, he didn’t have a problem. Bulger fixed him with what must have been a terrifying stare and responded, “We’re not friends anymore.”
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For twenty years, Whitey Bulger terrorized Boston with the full collusion of the FBI. On the run for sixteen years, he was eventually arrested on June 22, 2011.
Litif got off with this stern warning but then made the mistake of telling Bulger that he was going to murder his bookmaker partner, a last straw. On April, he was invited to the Triple O’s where Bulger stabbed him repeatedly with an ice pick and Steve Flemmi shot him in the head. His body was found in the trunk of his car, in garbage bags, abandoned on a South End street. In another example of his macabre sense of humor Whitey explained to associates afterwards that Litif, known as a flashy dresser, was wearing green underwear after they stripped his body. Therefore, they made sure that they used green garbage bags, so that Louis would be found, color coordinated.
Only a few months later, a Southie criminal named Brian Halloran tried to extricate himself from some serious criminal charges by going to the FBI, with details tying Bulger and Flemmi to the murders of Louie Litif and Roger Wheeler, even claiming to be an eye witness in both cases. Although Halloran was at least embellishing if not outright lying about his presence at the Wheeler slaying, he was close enough to Callahan to be able to secretly record potentially incriminating conversations. He pleaded to be allowed into the witness protection program and the agent handling his case figured he would run that by supervisor John Morris, to see what he thought. Morris immediately told Connolly who told Whitey Bulger.
With two bodies now buried in its basement, Whitey Bulger began referring to the Nee house as the Haunty. The cellar would have another permanent guest, Deborah Hussey, Steve Flemmi’s quasi-stepdaughter. Although he and Marion Hussey never married, he lived within the Hussey household and was perceived as the father in the family. That is, until Deborah Hussey revealed that Flemmi had molested her sexually, beginning when she was a young teenager. As an adult, Debbie developed a serious drug addiction and resorted to prostitution to feed her habit. Arrested on numerous occasions, she frequently named dropped both Flemmi and Bulger to the police. She also took to hanging around the Triple O’s and demanding drinks from the customers or hitting up Southie dope dealers for freebies, bragging that she had connections to Whitey, another big red flag. Bulger believed her to be a dangerous loose cannon and began pushing Flemmi to do something about it. In early January, 1985, Flemmi did. He got her to meet him by feigning guilt over what had happened between them and the general situation with her mother. He asked to make it up to her by taking her clothes shopping and telling her he was thinking of buying her her own place. Why don’t we drop by and take a look and see if you like it? The house in question was The Haunty.
Ambitious, Connolly was fully aware that for the FBI, the American Mafia to the exclusion of all other organized crime entities was the paramount target of Federal law enforcement. Aware that Steve Flemmi already had provided information, Connolly set his sights on forming the same relationship with Whitey Bulger. Thus far in his brief FBI career in New York, Connolly received high praise during his ongoing evaluations with the stipulation that he had not developed any confidential informants. The agent, knowing Whitey from the old neighborhood and willing to cut ethical and professional corners, understood that developing Whitey as a Top echelon informant could be, within the bureau, a career maker.
In the cat and mouse game of criminal informant, it quickly became clear that the lines were being blurred as to who was the cat and who was the mouse. John Connolly introduced Bulger and Flemmi to his newly installed supervisor within the FBI’s Boston Organized Crime Unit, John Morris. Connolly also arranged for regular dinners at Morris’ home in Lexington, Mass, dinners that included Whitey showing up with cases of very expensive wine, that always got left behind. Morris was blown away by Connolly’s ability to gain access to two such high level informants and was also manipulated by Whitey’s slick Robin Hood façade of claiming to abhor drugs, detesting the Mafia and keeping his neighborhood free from hard drugs like cocaine and heroin and the junkies and pushers who came with such pestilence. All of these claims were either ultimately self-serving or outright lies, but Morris was taken in.
In the late afternoon of June 22, 2011, in Santa Monica, California a property manager name Josh Bond was sitting in his office at the Embassy Hotel. Picking up the phone, Bond punched in the number of tenants from another property across the street, the Princess Eugenia Apartments at 1012 3rd Street, only blocks from the Pacific Ocean.
Whitey also made the most crucial connection of his criminal career when he began to interact with Stephen Flemmi, a member of the Winter Hill Gang who had ambitions of bigger and better things. Nicknamed “The Rifleman,” based on two Army tours of duty in Korea, in which he earned both a Bronze and Silver Star, Flemmi also had an ongoing relationship with longtime Boston FBI agent Paul Rico who specialized in developing informants in the New England criminal underworld.
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