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Sept. 26, 2013
Gerald Chapman became America’s first “celebrity gangster” and its first “Public Enemy No. 1.” President Coolidge pardoned him from the Federal charges against him so that the State of Connecticut could hang him.
by Robert Walsh
“Death itself isn’t dreadful, but hanging seems an awkward way of ending the adventure…”
– Gerald Chapman to his lawyers after being sentenced to death for murder in 1925.
We’ll call him “Gerald Chapman” as that was his favourite alias. His real name was probably George Chartres and he was born in New York in August of 1887 but, as records are sketchy and Chapman was always evasive about his early life, we’ll probably never know for sure. What we do know is that he was a thief, safecracker, armed robber, bootlegger, burglar, conman and cop killer and one of the first “celebrity gangsters” of the 20th century.
Chapman was born into a poor neighborhood on New York’s Lower East Side in August, 1887. Although he came from an honest family he began drifting into petty crime while still a young boy, little things at first like shoplifting, petty theft and so on. His first foray into the bigger leagues was an armed robbery that earned him a 10-to-15 year sentence at the notorious Sing Sing Prison. He was transferred to Auburn Prison (site of the world’s first electrocution) where his criminal career really began to blossom. Before his armed robbery conviction he was nothing more than a typical juvenile delinquent, one of many small-time neighborhood crooks destined to spend their lives going through the revolving door between freedom and prison, doing what some American crooks call “Life on the instalment plan.”
There didn’t seem like anything else in store for Chapman until he arrived at Auburn and met his criminal mentor and frequent accomplice, George “Dutch” Anderson.
The Mentor and the Pupil
Anderson was unusual in many ways. His real name was Ivan Dahl von Teler, he was from a prosperous family, was born in Denmark some time in 1880, had graduated from the universities of Heidelberg and Uppsala and dropped out of college in Wisconsin to take up a career as a professional criminal specializing in burglary, robbery and counterfeiting. He was a highly-educated and very intelligent man who, for some reason, chose crime as his career even though his prosperous background and education didn’t make it a necessity. When he met Chapman, Anderson was serving time for forgery and assault. Anderson was several years older than Chapman but, despite their difference in age and criminal experience, saw in Chapman a willing apprentice who had the brains and the nerve to learn the skills for big-league professional crime. Chapman saw a mentor in Anderson and a long-running criminal partnership was born. Without Anderson’s advice and tutelage it’s highly likely that Chapman would have been at best, a mid-level journeyman crook. With Anderson, Chapman went from being just another small-timer to one of the first celebrity gangsters and America’s first “Public Enemy Number One.”
Anderson took Chapman under his wing and taught him all he himself knew about crime. Chapman learned fast, discovering among other things that being outwardly respectable and acting like a gentleman was a good way to divert suspicion, that disguises were useful when committing robberies and learning the practical aspects of being a career criminal. Chapman dressed well, lived at better-than-average addresses and even took to using a stereotypical upper-class British accent. It’s ironic that Chapman (originally very much the junior partner) would become the celebrity gangster while Anderson (without whom Chapman would probably have amounted to little) faded into obscurity.
After several years at Anderson’s informal university of crime, Chapman was ready to graduate with honors. With time off for good behavior Chapman was paroled first and Anderson joined him in New York a few months later. Needing a driver to assist in robberies and burglaries, they recruited another Sing Sing alumnus, Charles Loerber, to be their wheelman and pose as their chauffeur while they set themselves up as wealthy businessman. Chapman posed as “G. Vincent Colwell” who had supposedly made his fortune in the oil business while Anderson (by now accepting that Chapman made a better frontman than he did) became his “business partner.” In 1919 the threesome set themselves up in a posh apartment in Gramercy Park (then one of New York’s more exclusive areas) and prepared themselves for the big time. The big time wasn’t long in coming.
The year 1919 marked the opening of what many Americans called the “Noble Experiment” of Prohibition. In theory, America would be scourged of many of its social problems by simply banning the production, sale and distribution of alcohol. In practice it was a disaster. It made American drinkers criminals, it handed a business grossing $2 billion a year over to gangsters and, perhaps most damaging of all, moved those gangsters from the role of public enemies to public servants. Chapman and Anderson were quick to spot its potential and set up bootlegging operations in Illinois, Wisconsin and Michigan to provide a steady income while planning what would be the biggest armed robbery in American history at that time. The gang also arranged a few lucrative confidence scams, travelling through the Midwest fleecing people as they went. It was Loerber who suggested robbing mail trucks and armoured cars. New York being home to all manner of brokerage houses, banks and Wall Street there were any number of potential targets for enterprising felons to choose from.
The Great Post Office Robbery of 1921
The U.S. Postal Service had delivery trucks running all over the city of New York and they often carried huge amounts of high-value cargo: Gems, jewellery, bearer bonds, negotiable securities and cash.Usually very large amounts of cash. Careful research pinpointed a truck running regularly along Leonard Street and the “Great Post Office Robbery” of 1921 was on. Before Leonard Street the gang robbed a couple of other armoured trucks as trial runs. These trial runs were lucrative, serving as dress rehearsals for the Leonard Street robbery.
The Leonard Street job was pretty simple as armed robberies go. Rather than risk being spotted in a stolen car, the gang bought a Pierce-Arrow and a Packard. Loerber used his mechanical skill to make them fast, nimble getaway cars. They followed the mail truck along Leonard Street, pulled over to block its path, assaulted the driver and guard and then made off with four high-value pouches. It was obvious from the speed of the robbery that the gang knew what it was doing and exactly what kind of pouches to look for. The job ran like clockwork and was over in a few minutes without a shot fired.
The take was more than the gang could have expected: $1.1 million of securities, stocks, bonds and cash even after the gang had disposed of anything that they didn’t think could easily be fenced. At the time it was the largest robbery in U.S. history and it wasn’t long before, being known felons with prior robbery convictions, Chapman and Anderson became suspects. That suspicion was confirmed by a private investigator who discovered the gang had taken an impromptu trip to Europe to try cashing some stolen securities. They didn’t find any buyers, but left enough of a trail to link them to a recent armoured truck robbery. The hunt was now on.
Robbing mail trucks was certainly highly lucrative, but greatly increased profits brought greatly increased risk. Mail robbery was a Federal crime (unlike bank robbery which, at the time, was still within state jurisdiction). Once the Feds began looking for the gang it was only a matter of time before they were found and heavy sentences handed down. It was no time for the gang to begin a spree of robberies in upstate New York when they should have been lying low, but they did exactly that. It proved to be their undoing.
Over the next few weeks they pulled one job after another. They robbed five banks and several major stores before opting for another armoured truck heist. This time they decided to try their luck with the American Express Company and, while their luck lasted long enough to pull the job and split around $70,000 after expenses, it didn’t last once a private investigator traced them back to New York City where Chapman and Anderson were both arrested.
It wasn’t until detectives and Federal agents questioned them about the American Express robbery that they realized they’d accidentally picked up two of the Leonard Street robbers. Chapman started needling them, repeatedly denying any involvement in Leonard Street while apparently gazing round and round the room as though he was looking for something. It became obvious exactly what he’d been looking for when he simply said “Sorry, gentlemen.” before dashing across the room and out through a third-floor window. While Anderson was left glowering at a detective who quickly aimed a gun at his head, other officers rushed to the window and looked down to see if they could spot Chapman’s body on the street below. Instead of a body they soon saw a witness in a window across the street waving and pointing to alert them as Chapman teetered along the window ledge and in through another window. It did him no good. Officers simply went along the corridor searching every room facing the street and in the fourth office along the corridor they soon found Chapman. Within seconds of they had him handcuffed and shipped him off to jail to await trial.
Sentenced to 25 Years in Federal Prison
Both men firmly denied the mail truck robbery and the American Express job, but it did them no good. The evidence was overwhelming and guilty verdicts were almost a formality. So were their harsh sentences. Both drew 25 years at the Atlanta Federal Penitentiary and were quickly shipped off to serve their time, much to the delight of their victims and law enforcement. The smiles on their victims’ faces (and those of the authorities) would be wiped off in short order.
Neither felon had any intention of cooling his heels in Atlanta for anything remotely resembling 25 years. What they both intended to do was serve as little time as possible while preparing to escape. It was only a matter of months before Chapman went from being a jailed convict to a wanted fugitive when he escaped on March 27, 1923. Chapman’s 25-year sentence had lasted precisely seven months and four days. With a fellow inmate, forger Frank Gray, Chapman faked illness to get into the less-secure prison hospital. Once there, they attacked a guard, forced a window bar and climbed down the hospital wall using a rope made from knotted sheets. Now they were in the prison yard faced with the tricky problem of a wall covered by bright lights and armed guards. If the guards saw them they’d readily shoot on sight.
Chapman had that covered. He knew from another inmate that the wires supplying the lights ran just below the top of the wall. Once he was on top of the wall he used a rubber-handled knife to strip the wires and carefully draped a length of copper wire across them, short-circuiting the power supply. The resulting blackout provided Chapman and Gray with all the time and concealment needed to climb down their home-made rope and disappear into the night.
It didn’t last. Less than 48 hours later they were surrounded by a heavily-armed posse of over 200 men not very far from Atlanta. Gray surrendered after a couple of warning shots, but Chapman wasn’t as compliant or as sensible. He tried to outrun the posse and took bullets in his arm, hip and back. One of the bullets went through his kidney and for a while it looked as though he was going to die. He wasn’t, not by a long shot.
Six days later, on April 4, 1923, Chapman escaped again and, if anybody was in the line of fire it was the staff of Atlanta Federal Penitentiary. Having been shipped to Athens General Hospital (rather than the prison infirmary) security wasn’t nearly as tight as it might have been and while Chapman’s body might have been seriously damaged, his criminal mind was as sharp as ever. He carefully cased the routine of the three guards who watched him 24 hours a day and, soon enough, he found the opening he was looking for. At one point (when he should have been under permanent guard) he was left alone in his room with a nurse who asked him if he wanted to sleep. He did. The nurse turned out the light and went off to her other duties. When she returned to check on her patient, only 22 minutes later, he was gone.
The alarm went up again and, given Chapman’s injuries, officials quickly guessed that he couldn’t have gone very far and might even be hiding inside the hospital itself. They were right. The hospital was thoroughly searched and on April 6 Chapman was found hiding in the basement. From the penitentiary’s point of view, their thoroughly vexatious inmate was now back under guard and would soon be back at the penitentiary to finish almost all of his 25 years. He wouldn’t be under guard for very long.
Chapman had been overheard moving around the basement by a nurse who promptly summoned one of Chapman’s guards to investigate the suspicious noises. Once Chapman had been identified the nurse promptly panicked and, while the guard was fully occupied trying to calm her down, Chapman saw his chance. Once more he vanished into the night and this time managed a clean getaway. The public couldn’t get enough of the story or of Chapman and the American press dined out on the story for weeks. Whether the staff members of Atlanta Federal Penitentiary were left cursing the day Chapman ever became their problem isn’t a matter of public record, but it’s a pretty safe assumption that they were. It wouldn’t be the last time they had cause to do so, but we’ll get to that later.
America’s First “Public Enemy No. 1”
Chapman was now a media darling and public anti-hero, a celebrity gangster long before John Dillinger made it fashionable, Al Capone built his own personal legend and John Gotti devastated the Gambino family through his insatiable desire for column inches. Chapman gained column yards and one reporter christened him America’s first “Public Enemy Number One.” He couldn’t have been any more famous. Unfortunately for Chapman, the more his legend grew the more effort and resources law enforcement devoted to tracking him down and making an example of him. Like many a famous American outlaw he had his supporters and his detractors, many people rooted for him and he made terrific tabloid-fodder for the press. The end result of his career wasn’t really in any doubt. He’d be captured, killed or executed sooner or later like so many of his predecessors, but it would be a wild ride (and sell a great many newspapers) while it lasted.
Of course, like all great double acts, Chapman needed his straight man, the problem being that George Anderson was still serving his own 25 years and was a somewhat unlikely candidate for early parole. Anderson, to the delight of the media, their readership and Chapman (though definitely not the staff at Atlanta) conveniently solved that problem. If the State or Federal authorities were unwilling to arrange early release then he’d simply arrange his own without the tiresome bureaucracy of the parole board. On June 23, 1924, Anderson escaped from Atlanta and, seeing as he was never the media darling that Chapman was, the press used his escape as yet another chance to recap Chapman’s exploits for their voraciously-interested readers.
Chapman laid low for a while, but it wasn’t long before his name made the front pages again. The date was October 12, 1924, the place was New Britain, Connecticut and the charge was capital murder. Two men were spotted breaking into a department store and five police officers rushed over to arrest them. There was a shootout between the burglars and the officers. Patrolman James Skelly was killed while one of the burglars was arrested. It was the beginning of the end for Gerald Chapman.
Conviction for Murder
The prisoner was one Walter Shean, the black sheep of a wealthy family from Springfield, Massachusetts. Once arrested and offered a simple choice between identifying his accomplice or being hanged for murder, Shean quickly cracked. He told his questioners that he knew his partner as “Waldo Miller,” but was certain that Waldo Miller was actually Gerald Chapman. It took three months for police to finally capture Chapman, which they finally managed in Muncie, Indiana in January, 1925. Along with Anderson, Chapman had been in hiding as a paying lodger with a farmer named Ben Hance. Hance would later be the star witness at Chapman’s trial and had tipped off police that his lodgers were behaving suspiciously. It was a public-spirited gesture that would see Chapman safely under lock and key. It would later cost Mr. and Mrs. Hance their lives.
Chapman was extradited to Atlanta to serve his remaining time while Federal and state authorities quickly started haggling over issues of legal jurisdiction. The Federal Government had jurisdiction in that Chapman was a Federal inmate, but the State of Connecticut wanted him to face trial for the murder of Patrolman Skelly. Connecticut wanted Chapman and, at first, the Federal Government wouldn’t hand him over. After a certain amount of horse-trading the Feds agreed that, while Chapman would remain a Federal prisoner and thus had no chance of getting or jumping bail, he could still be extradited to Connecticut for trial in the Skelly murder. In March, 1925 he was removed from Atlanta under heavy guard and found himself lodged at the Connecticut State Prison in Wethersfield. Aside from trial and appeal hearings, Chapman would never leave Wethersfield alive.
The trial was as could be expected, another media circus. Given that the evidence was overwhelming and the penalty for murder was death, the press knew that they wouldn’t have too long to milk the story so made every effort to do so while Chapman was still alive. The trial was also virtually a forgone conclusion. Shean identified his partner in the New Britain robbery and Gerald Chapman as being one and the same. Hance firmly identified Chapman as one of his suspect lodgers and some burlap sacks from the Hance farm were identified as being in Chapman’s possession during the New Britain robbery, presumably to be used to carry away swag. Walter Shean might not have made the most appealing prosecution witness but the honest, consistent evidence and homespun demeanour of Ben Hance completely demolished Chapman’s somewhat desperate defense. Chapman’s defense, such as it was, consisted of his never having visited New Britain, never having met Ben Hance or Walter Shean, and simply not being Gerald Chapman. It probably didn’t help that bullets and spent cartridges from Chapman’s gun matched those from the crime scene and Patrolman Skelly’s body, either.
The jury took only 11 hours to deliver a verdict. On April 4Chapman was found guilty as charged of capital murder. The judge passed sentence and Chapman was shipped back to Wethersfield Prison to await execution. It was now that the jurisdiction issues raised their ugly head once more.
Chapman’s lawyers argued that, as a Federal prisoner, he would have to serve his full sentence before he could be handed over to the State of Connecticut for execution. The appeals went as high as the U.S. Supreme Court before no less a figure than President Calvin Coolidge personally intervened to resolve the matter. After three stays of execution the prosecuting attorney went to the Attorney General of the United States in Washington and personally requested that Chapman be given a Presidential pardon for his 25-year sentence. If granted the pardon, Chapman would cease to be a Federal inmate, making him instantly available to Connecticut for execution and neatly cutting through all the jurisdictional red tape between Chapman and his date with the hangman.
A Presidential Pardon with a Deadly Twist
What couldn’t be arranged by the prosecution or various judges over the previous few months could be, and was, settled by the Attorney General in an afternoon. After meeting with District Attorney Alcorn he promptly consulted President Coolidge and only two hours later Alcorn had in his briefcase a signed Presidential pardon. The pardon freed Chapman from his Federal prison term. It also freed the State of Connecticut to hang him. But that wasn’t quite the end of the Gerald Chapman saga.
Chapman’s lawyers took the legality of the pardon back to the U.S. Supreme Court. They argued, somewhat desperately, that as Chapman had neither requested nor accepted the pardon then it had no basis in law. The Supreme Court thought otherwise. In its ruling upholding both the pardon and Connecticut’s right to proceed with the execution, the high court stated that a Presidential pardon is a legal act and, as such, required no discretion whatsoever on the part of the prisoner concerned. It didn’t matter that Chapman didn’t ask for or want a Presidential pardon. The pardon stood, so did the death sentence awaiting the prisoner and, in an unusually terse remark, the Supreme Court ruled in so many words that Federal jurisdiction does not exist as a sanctuary from State justice. Seeing as almost all of his other arguments had already been ruled upon and dismissed, the ruling effectively unlocked the door to the death chamber for Gerald Chapman.
His absolute last resort was a final hearing before the State Board of Pardons and Paroles. The board wasn’t buying. Chapman did himself no favors by mounting numerous personal attacks on District Attorney Alcorn and, being so notorious a criminal who’d caused both state and Federal authorities endless trouble, the outcome was never really in doubt. Chapman was denied relief and handed a death warrant instead. On June 25, 1925, he would be taken from Death Row at Wethersfield Prison and hanged by the neck until dead.
The “Upright Jerker”
I quoted Chapman earlier as saying that death didn’t bother him, but hanging would be an awkward way for him to die. He was right, it was. Most states that still employed hanging used a conventional gallows. Connecticut was still using an old invention known as the “upright jerker.” Instead of standing on a trapdoor and being dropped into eternity, a prisoner would stand inside a marked square on the floor while guards applied the restraining straps and a black hood. Once the prisoner was strapped and hooded the rope was lowered from the ceiling, placed around the prisoner’s neck and the prison warden stepped on a large metal button rather than pushing a lever. When the button was pressed steel counterweights weighing 300 pounds were released. The dropping of the weights would violently jerk the prisoner into the air, fracturing the neck and bringing instant, painless death.
There was only one small problem with this device; it didn’t always work very well. British hangmen calculated specific drops using a printed “Table of Drops,” a mathematical equation related to the prisoner’s weight and muscle tone, ensuring as personalized and accurate a drop as possible. The upright jerker gave every inmate the same degree of force and couldn’t be altered in any way at all, giving the same force to every inmate regardless of the individual’s physical characteristics. The upright jerker had long been discarded elsewhere after numerous inmates were slowly strangled instead of instantly killed. It became so detested that several botched executions in New York State (the last being a woman, Roxalana Druse) caused the New York State Legislature to consider other methods, eventually provide the world with both an entirely new method and a brand new word to describe it. The word was “electrocution.”
Accounts of Chapman’s execution vary. Officially, the upright jerker worked perfectly and Chapman died instantly. Other reports state quite bluntly that his neck wasn’t broken and that he spent nine minutes dangling above the assembled witnesses before he finally died. Either way, Gerald Chapman, America’s first Public Enemy Number One walked unaided into the death chamber at Wethersfield Prison on June 25, 1925 and was wheeled out on a hospital trolley. America’s first celebrity gangster was dead.
“Dutch” Anderson wasn’t. Anderson had remained a fugitive and now swore vengeance on anybody involved in Chapman’s trial and execution, especially prosecution witnesses and even the prosecutor and his family. Alcorn and his family found themselves under 24-hour guard against Anderson’s openly stated and highly credible threats. Walter Shean was also put into protective custody to give him a better chance of serving his jail sentence and leaving jail alive.
Ben Hance and his wife weren’t so lucky.
Ben Hance had been especially worried about gangland vengeance, especially considering that Anderson was still at large. He wasn’t offered any bodyguards and no Witness Protection Program then existed. He was just told after the trial to go home, pick up his daily routine and try to forget about any threats made. He did his best to do that. The problem being that, while Hance was doing his best to forget Anderson, Anderson still retained a keen and homicidal interest in Hance.
While in hiding at the Hance farm, Chapman had installed a telephone. Now that Chapman was gone the Hances found the phone very useful, especially when taking orders from people buying sacks of dried vegetables as another way to earn a little extra money. Times were hard for sharecroppers so every little helped. On August 15, 1925, Ben Hance answered the phone and took an order for a couple of sacks of peas and beans. The customer also asked him to deliver somewhere along the Middletown Turnpike, only a short drive from the farm. Hance asked his wife if she fancied coming along for the ride.
It would be the last time either of them was seen alive.
The Hances loaded their Model T Ford and set off to make a little extra money. Along the Middletown Pike they saw a shiny, expensive-looking saloon car. Realizing that these were their customers they slowed, stopped and then realized who they’d just been reacquainted with. It was George Anderson and a minor member of the Anderson/Chapman gang, Charlie “One Arm” Wolfe.
A car chase ensued with the Hances trying desperately to outrun their killers. Wolfe managed to cut across in front and force them to stop. Anderson did the rest, unloading a barrage of .45 bullets through the windshield. Mrs. Hance died without even managing to leave the car. Her husband didn’t last much longer. He was found lying beside the wreck riddled with bullets from Wolfe’s automatic. Anderson and Wolfe went their separate ways, leaving their victims behind them.
Anderson’s luck held for only a few more weeks. He began drifting round the Midwest having returned to one of his previous rackets, passing forged currency. He turned up in Muskegon, Michigan on October 31, 1925 and began buying small items with fake $20 bills, pocketing the genuine money he got in change. Unfortunately they were very bad fakes and, given that he’d passed a lot of them in many different places, it wasn’t long before a storekeeper handed one to a police officer with a description of the customer who’d just passed it. Patrolman Charles Hammond went looking for anybody matching the description and, sadly for both of them, he found Anderson.
Anderson tried at first to bluff his way out but Hammond became increasingly suspicious. Anderson also knew that if Hammond took him to the nearest police station he’d be unmasked and very likely extradited to Indiana for the Hance murders. Extradition to Indiana meant, equally likely, a seat in the electric chair at Indiana State Prison. Bluffing hadn’t worked. Anderson could only run, fight, or both.
Anderson ran. Unfortunately he ran into a blind alley, leaving himself trapped with Patrolman Hammond in hot pursuit. Bluffing hadn’t worked. Running hadn’t worked. All he could do was shoot his way out and he tried to. As Hammond cornered him Anderson drew his gun and the two men traded bullets. Hammond missed, Anderson didn’t. Hammond was shot in the groin and Anderson went to step over his body and flee. Despite his mortal wound, Hammond grappled with Anderson, disarmed him and during the struggle Anderson was shot through the heart. He died minutes later. Hammond died shortly afterward.
Chapman’s Legacy Snares Lepke Buchalter
That was almost the end of the Gerald Chapman story. Chapman and his mentor were dead and buried and it was doubtless hoped by some that his name and career would eventually fade into obscurity. But Chapman, always the “celebrity gangster,” did manage to rise from the dead and grace one final set of newspaper headlines. In 1941, notorious mobster Louis Lepke Buchalter was serving time as a Federal inmate, convicted on narcotics and racketeering charges. Buchalter had willingly taken a 14-year sentence under Federal law as he thought it would keep him from facing a capital murder trial in New York State and give him the length of his sentence to bribe, intimidate or murder prospective witnesses. One of Lepke’s golden rules was, after all, his infamous remark “No witnesses, no indictments.” He was fatally mistaken.
Buchalter, to his bemusement and surprise, was given a very-much-unwanted pardon on his Federal crimes and then shipped from Leavenworth Prison to New York. Things went from bad to worse for Lepke when he was convicted in a New York court on racketeering charges adding another 30 years to his existing sentence but, in 1941, he was appalled by something far, far worse. One of his underlings facing a potential death sentence on a murder charge was one Abe “Kid Twist” Reles. Reles made a deal with prosecutors that he would testify against former accomplices in many unsolved crimes and also against those who ordered those crimes. Once Reles flipped the arrests came thick and fast and one of those arrested was professional hit man Allie “Tick Tock” Tannenbaum.
One of the most regular customers of the notorious New York murder-for-hire ring known as “Murder Incorporated,” Lepke was tried for ordering (among many other murders) the contract killing of Joseph Rosen in 1936 after Rosen threatened to testify about Lepke’s numerous racketeering enterprises. Tannenbaum wasn’t involved in the Rosen hit, but he had heard Lepke order it so under New York law he could corroborate the testimony of Reles and other Murder Inc. turncoats. Tannenbaum’s corroboration, as someone who knew the details but wasn’t actually involved in the murder itself, was absolutely essential in gaining convictions and death sentences for Lepke and two of his most senior henchmen.
After considerable legal battles between his defense lawyers (who used a similar strategy to Chapman’s lawyers), the Federal Government and New York State, President Franklin Roosevelt cut the red tape in the same way as President Coolidge had done. The Gerald Chapman bandwagon rolled one last time as the case was sent right up to the U.S. Supreme Court before Lepke was finally handed over to New York, tried, convicted and condemned to the electric chair. He was eventually executed on March4, 1944 at Sing Sing Prison along with accomplices Emmanuel “Mendy” Weiss and Louis Capone (no relation to Al).