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Crash Out: The True Tale of a Hell's Kitchen Kid and the Bloodiest Escape in Sing Sing History

Crash Out: The True Tale of a Hell's Kitchen Kid and the Bloodiest Escape in Sing Sing History

by David Goewey

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The enthralling and evocative story of tough Depression-era bandits who vowed to make something of themselves, even if that meant defying the stone walls of America’s most infamous prison, by a writer who grew up in Sing Sing’s shadow.

During an era of never-ending breadlines and corrupt cops, no place churned out budding crooks more efficiently


The enthralling and evocative story of tough Depression-era bandits who vowed to make something of themselves, even if that meant defying the stone walls of America’s most infamous prison, by a writer who grew up in Sing Sing’s shadow.

During an era of never-ending breadlines and corrupt cops, no place churned out budding crooks more efficiently than Hell’s Kitchen. Neighborhood loyalties bonded gangs of immigrant sons who were looking for a way out of 1930s New York, and waterfront kids like Whitey Riordan paid the bills with small-time hustling. But when enterprising crook Patches Waters invited Whitey into the Shopping Bag Gang, Whitey jumped at the big score. Bold black headlines announced the group’s string of successful heists, but the gravy train abruptly halted in 1939 when someone squealed and police captured most of the gang. Patches and Whitey were sent up the river to Sing Sing.

Westside connections couldn’t help much there, in the infamous Hudson River prison that had housed convicts for more than a century. In Sing Sing the boys had to answer to veteran warden Lewis Lawes, a revolutionary reformer who preferred trust and rehabilitation to old standbys like the lash and the yoke. Progressive indeed, but nothing changed the fact that Whitey and Patches, along with more than 2,800 other men, faced a future of endless days in a cage of limestone, cement, and steel. Perhaps inevitably, their thoughts turned to escape.

A string of well-publicized jailhouse riots and breakouts captured the country’s interest in the 1930s, and though prisons kept stepping up security, convicts continued to crash out. When Patches encountered an old cellblock crony who had stumbled upon a way out, he pieced together a daring escape plot involving purloined guns, counterfeit keys, precision timing, a complex network of outside accomplices, and the kind of outsize bravado that would have made Dillinger proud. Unable to resist the thought of freedom, Whitey signed on. On Easter Sunday 1941, the three embarked upon the most sensational breakout in the prison’s history. Leaving four men dead and indelibly staining the reputation of the nation’s most famous warden, the Westside boys transcended their wildest dreams, only to find themselves backed to the edge of a wide, dark river.

Meticulously researched and beautifully written, Crash Out is a gritty, page-turning saga that reveals how the career of one resilient hustler can illuminate a sliver of Americana.

A riveting account of the boldest escape in Sing Sing history and the gangster culture that birthed the defiant bandits, Crash Out is a gripping historical epic set against the fascinating backdrop of Depression-era New York.

From the Hardcover edition.

Editorial Reviews

Publishers Weekly
Displaying polish and a gift for crafting a gripping narrative, Goewey's debut brings to life an episode that will be unfamiliar to most: the 1941 escape from the legendary Sing Sing prison that claimed the life of a guard and a local policeman. The author, identified as "the grandson, son, and brother of Sing Sing officers," has done extensive research and makes the depressed atmosphere of Hell's Kitchen between the world wars vivid and three-dimensional. His account achieves balance by alternating between the perspectives of Whitey Riordan, one of the thugs in the "crash out" from the prison, and progressive warden Lewis Lawes. The escape itself is less memorable than the grim depiction of Riordan's dead-end world and the warden's attempts to run his fiefdom without diminishing the humanity of the inmates. The author's failure to elucidate the significance of the prisoners' attempt to gain freedom will make the whole less than the sum of its parts for some, but the skill Goewey demonstrates will lead many to hope he turns his attention to other forgotten tales. 8 pages of b&w photos not seen by PW. Agent, Brettne Bloom. (Nov.) Copyright 2005 Reed Business Information.
Library Journal
First-time author Goewey was born and raised in Ossining, NY, where Sing Sing prison stands, and there have been generations of Sing Sing officers in his family. Here he describes the boldest and bloodiest escape in the prison's history-the Easter 1941 "crash out" in which four prison officers were killed by inmate gangsters Whitey Riordan and Patches Waters. (The prison still holds a memorial service for the officers every April 14.) Riordan and Waters were originally from New York City's notorious Hell's Kitchen neighborhood. Goewey provides an extensive description of their tough childhoods and subsequent rise to crime and gangsterism. Waters invited small-time crook Riordan to join his thriving Shopping Bag Gang. When the gang was busted, the two each received 15 years in Sing Sing. Goewey offers a detailed history of the prison, which had named itself after the town (the town later changed its name to Ossining to differentiate itself). Ultimately, Riordan and Waters were captured, sent to trial, found guilty, and executed in the electric chair. Crash Out is a well-written book that may appeal to the criminal justice specialist more than the casual reader. Recommended for large public libraries.-Tim Delaney, SUNY at Oswego Copyright 2005 Reed Business Information.
Kirkus Reviews
The notorious Sing Sing prison may be the most memorable character in this grim tale of crime and punishment. Home of the electric chair in which 614 men and women (including Julius and Ethel Rosenberg) were executed, it was the setting for James Cagney's famous "last mile" walk in the film Angels with Dirty Faces and several other 1930s B-movies. Goewey, the son, grandson and brother of Sing Sing guards, effectively relates the infamous prison's lore. He also does a creditable job of re-creating the grimy pre-World War II Hell's Kitchen neighborhood that serves as the story's other major backdrop. It was there, amid the West Side waterfront and nearby tenements, that "Whitey" Riordan and "Patches" Waters grew up, young street toughs whose hardscrabble childhoods seemed inexorably to lead to depressingly brief lives of crime. Riordan was first arrested in 1927, at age 12, and spent much of his life in and out of prison. He later joined neighborhood pal Waters to form the notorious "Shopping Bag Gang," resulting in their jailing at Sing Sing in 1940 following a string of armed robberies. Unfortunately, Riordan, Waters and their "breakout" partner, another hardened con named Charlie McGale, hardly make for intriguing characters. Small-time hustlers turned career criminals, they never rise above the level of unsavory hoodlum. Moreover, the infamous "crash out" recounted here turns out to be a comedy of errors in which the carefully conceived escape plan collapses even before it begins, leading to the deaths of two police officers. Adding to the anticlimactic feel of the story is the fact that our Sing Sing fugitives were captured within a few miles of the prison only hours after theirescape. Oddly, Goewey never provides the names of the police officers who brutally interrogated the captured fugitives, beatings that would have surely warranted a full-scale investigation today. It's also disappointing that he doesn't include any of the numerous photographs that documented the capture and subsequent trial. A less than compelling crime-doesn't-pay saga.

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Chapter One:Robbers. Monday, May 15, 1939

Joseph “Whitey” Riordan, convicted thief, strong-arm, and current hiring boss on New York’s waterfront, stepped outside his family’s Isham Street apartment at dawn like it was any other workday. The Monday morning sky was clear, turning blue, with the night still close to the pavement. On spring days like this, Whitey could smell the new leaves in the breeze drifting down from Inwood Hill Park up the street—damp woods skirting the tidal flats on Manhattan’s northern tip. The city’s wildest park remained almost unchanged since the time of the American Revolution. You could still catch sight of deer, even fox, in the deeper groves. But now the year-old, gleaming steel Henry Hudson Bridge, spearing out of that wilderness into pricey Riverdale, gave New Yorkers another way out—an escape route north to the suburbs.

Whitey Riordan saw limitless possibility, too. But right here in Manhattan. By six that evening, he could be richer by a thousand dollars, maybe two thousand. Across Isham Street, Good Shepherd Church rose in thick granite blocks, lights from an early Mass sparkling through the stained-glass windows. When the Riordans moved uptown, Whitey’s mother, Elizabeth, loved the thought of living across from the church. A lifelong Catholic, she must have hoped the cross and steeple right outside the front door would influence her wayward sons. Whitey probably shrugged it off—his money had helped their move, and his mother hadn’t kicked then.

To the east, radio antennas on apartment rooftops etched the sky above Broadway. A few blocks beyond those buildings, on the Harlem River shore at 212th Street, Manhattan’s last working farm prepared fields for the produce they’d send down to markets on Ninth Avenue, in Whitey’s old neighborhood of Hell’s Kitchen. A city boy at heart, the thought would have made him smile—Inwood seemed a continent, a whole lifetime away from the brick tenements and back alleys of his childhood.

Whitey often caught a car ride down to the docks with some other longshoremen from the neighborhood. Today, though, he preferred the IND subway. He could easily afford the nickel fare, and the fewer people with knowledge of his routine that Monday, the better. Only recently had the A train tunneled this far north, following the crowds of mostly Irish New Yorkers like the Riordans, escaping Hell’s Kitchen’s trash-strewn confines for Inwood’s leafy air. For Whitey, though, the future was still rooted downtown on the West Side waterfront.

As hiring boss, or stevedore, Whitey shaped crews at Pier 90 on the North River, as the Hudson was then called, at the end of West Fiftieth Street. The job was one of the best on the docks. Out of the hundreds of men who gathered at the pier gates for the shape-up at 7:55 every morning and 12:55 every afternoon, Whitey chose crews of twenty or so to load and unload the passenger liners that steamed into port. Then he spent the rest of the afternoon playing cards or shooting the breeze in the dock office or union hall on Twelfth Avenue. Today, though, he’d have to hotfoot it right after the noon shape. His partner, John “Patches” Waters, and the gang were meeting at Little Joe’s around two thirty, and Whitey didn’t want to be late.

The boys were on a roll. In the past seven months, they had pulled half a dozen armed heists and swiped riches far beyond their imaginations. Just the thought could make a thief’s adrenaline surge. But the gang—Whitey, Patches, Willie the Greek, Lulu, Rusty, and Mac—all understood by now that precision timing was the key to their success. Anyone sloppy enough to be late to a job lost out.

Quick exits from dockside weren’t a problem, not for Whitey, anyway. If he had to go, he went. He didn’t need to punch a time clock—he was an inside man and lived by other rules. A husky young tough with thick blond hair that inspired his nickname, Whitey put rough longshoremen to work and took no lip about it. Besides, dock boss David “The Beetle” Beadle, who ran the loading for the Cunard White Star Line, was a reasonable man. So long as Whitey cleared it first with the Beetle—no details whatsoever—and kicked back a percentage from any unnamed outside interests, the young stevedore could do as he pleased. Their arrangement was nearly as old as the shipping industry itself. Though the target of numerous probes throughout the 1930s, most recently by the New York Police Department’s Riverfront Squad and the city’s district attorney, Thomas E. Dewey, waterfront rackets were as deeply entrenched in the West Side as the pilings that anchored the tarred wood piers in the muddy Hudson.

That May morning, the train racing downtown underneath Eighth Avenue, Whitey could only have wondered at the straight-johns crowded around him, red-faced in their neckties, Daily Mirrors under their arms. How did they do it? Locked in office jobs if they were lucky—in the unemployment office if not—and saddled with hungry kids, they had nothing to look forward to. Certainly not living life on their own terms, that was for sure. Despite his gutter beginnings, Whitey had it made over them. He had found his own way, was playing another angle, as Patches put it. Thanks to Patches, Whitey was looking at another big score, more than enough to spend and still pad things for quite a while. Add that to his plum dock job, and twenty-four-year-old Whitey Riordan was on top of the world.

The bartender at the Yankee Tavern on Ninth Avenue wouldn’t have been surprised to see Patches Waters that Monday noon, squinting around a cigarette and penciling figures on a sheet of paper. The elevated IRT—fifty-five feet above the street and right outside the door—thundered past regularly, rattling the bottles against the mirror behind the bar. But it took a lot more than that to distract Patches from his accounts. He frequently took in over $80 a week—more than sixteen hundred nickels converted to bills—from the two pinball machines he leased to the tavern. Combine that with the other machines that Patches had running in bars and candy shops around the West Side, and he stood to make over 250 bucks gross a week. Not fantastic, but not bad, either—twenty-eight-year-old Patches was just starting out with this pinball racket, after all.

Back in 1933, Mayor Fiorello LaGuardia had cracked down on gambling. While the flashbulbs popped, LaGuardia took a sledgehammer to a pile of slot machines, then ordered his men to dump the ruins into Long Island Sound. But the “Little Flower,” as the mayor was nicknamed, probably hadn’t figured on a kid’s game like pinball taking the place of the slot machines so quickly. Patches Waters, his associates, and hundreds of other enterprising businessmen (as Patches thought of himself) rushed to fill the barroom corners left empty by the busted slots, many signing leasing deals with Amalgamated Vending, a shady distributor on Broadway. Now pinball gaming was a favorite of drinkers and school kids alike, and the mayor’s office estimated that the racket took in over $20 million a year citywide. Patches wasn’t seeing that kind of cash, but he was doing all right. Certainly he could afford $2 for a cheeseburger and a very good tip. Besides, he had other means.

The job later this afternoon—the Harlem branch of the Consolidated Edison Company—would be another big score. The take could be as much as two grand per man. Definitely the rewards of a misspent youth. As for his past, Patches wouldn’t have had trouble putting a dollar figure to that, either. Some nickel-and-dime stuff when he was a kid, charges dropped. Fourteen months at the Catholic Protectory for attempted burglary when he was fifteen—didn’t get a cent from that job. Two years at Elmira Reformatory for a $6 holdup when he was seventeen. All told, his entire childhood probably came in under $10. Penny-ante. While Tammany Hall and Mayor Jimmy Walker were fleecing the city for millions all through the twenties—everybody from the mayor to the neighborhood cop to the borough dogcatcher had his hand out—teenage Patches was stealing his share, too. The only difference was that Patches, and thousands of other young goons breaking midnight windows, were marched before judges as crooked as themselves. The street thugs were sent away, while the official looters were rewarded with titles, became “Your Honor” and “Esquire.” Well, nobody ever said life was fair. That’s why you had to live for today.

By the time he was of legal age, Patches was seeing real money. Over $2,000 for his part in a Westchester bank holdup four years ago, when he was twenty-five. The good times didn’t last, though (they hardly ever did), and he served forty-five months at Sing Sing on a subsequent gun charge. When he got out a year and a half ago, he was determined to set himself up nicely. And now here he was with a flush, nearly legitimate business, and a very profitable racket on the side. His quick prosperity could be glimpsed in the bar-back mirror—the stylish sharkskin suit, the white shirt collar flared across the lapels—the sharp appearance a Daily News photographer would snap in a few weeks’ time. Patches’s life was finally clicking along, cherries straight across, and tonight looked to be just as sweet.

Patches needed to meet the boys at Little Joe’s apartment on East Twenty-fifth by two thirty. If a similar caper—the Con Ed office on Audubon Avenue in Washington Heights the previous December—was any indication, today’s job would call for a celebration. Maybe he’d stop by Gert’s house afterward, take his girlfriend out to dinner and dancing, make a night of it. Perhaps a movie, too—the sunlight outside flickered through the El tracks like a picture show projector. Like most crooks, Patches must have craved a stickup’s razor thrill, the adrenaline edge when an impending job would rev inside him all of a sudden, thudding against his chest. This was the way of the world.

If you didn’t play an angle, somebody would play it for you.

The target would be packed. Twelve tellers, plus about five managers, clerks, and other floorwalkers, not to mention a hundred pencil pushers manning the desks in the brick building’s second floor, and who knew how many customers. The Consolidated Edison Harlem branch office, its plate-glass display windows fronting one hundred feet of busy sidewalk on West 125th Street, seemed no simple knockover. But that depended on where you got your information.

Jake the Butch, a gem burglar with an eye trained for perfect setups, had cased the branch for the gang. It looked to him to be a prime touch worth the risk. According to Jake, the local utility company’s combined operations could work to the gang’s advantage. It was a cash business. A dozen tellers’ cages lined the west wall, and a spacious floor area showcased electrical appliances for sale. Customers could mail in their utility bills, if they wanted to. But Con Ed enticed the strapped and busy New York consumer with a convenient shopping experience—pay while browsing the latest GE “Flat Top” electric refrigerators (such an advance over the old-fashioned, domed Monitor Top). See something you like, all shining chrome and porcelain, you could tack on payments to your monthly bill.

Depending on how the gang played the crowd, the showroom could provide the ideal diversion for a quick heist. The merchandise piled high in the front windows blocked the passerby’s view, and the showroom’s rear exit opened onto a small weedy lot on a quiet residential street, across from Mount Morris Park—perfect for idling a getaway car. The gang could slip in and out, hidden in plain sight the whole time. It seemed too good to be true, but Jake’s intelligence was usually sound. Though not a holdup man himself, Jake had sold the gang his slant on the December job, and that had come off like silk. His information wasn’t cheap. Three hundred bucks, nearly $4,000 to a twenty-first-century crook. But if Jake was right, his take would be worth the investment.

There was no reason to notice the large Buick sedan with Massachusetts plates as it eased out of the afternoon rush-hour traffic and coasted to a stop at the curb outside the office at 32 West 125th Street. The block between Fifth and Lenox Avenues was bustling. A mixed crowd of pedestrians—Caucasian shoppers from Morningside Heights and Manhattanville and African American employees done working for the day in the strip’s Italian and Jewish-owned restaurants and stores—browsed the shop windows as the dinner hour approached. Some stopped to buy popcorn, peanuts, or steaming sweet potatoes from the pushcarts that teetered up and down the sidewalk on squeaky, cast-off baby carriage wheels, thickening the air with a mixture of grease and kerosene smoke. The sedan’s doors swung open and five men climbed out. The lively crowds swarmed around the men as they gathered for a moment on the sidewalk. If anyone did observe them, no one mentioned it to police afterward.

The late afternoon sun, hazy behind a southerly flow that had raised the temperature all day, slanted across the street and fell on the opposite sidewalk. Just outside the Con Ed office, though, the shade was cool, and you could smell the Atlantic Ocean in the breeze. Above the main entrance, a blue and orange 1939 New York World’s Fair flag flapped idly. As the Buick drove off into the honking traffic and disappeared around the corner of Fifth, the men, dressed neatly if anonymously in browns, grays, and blues, exchanged glances. They shifted the paper bags folded under their arms but said nothing. One last quick look left and right to check for cops. Then they shouldered their way through the pedestrians and entered the office as a group.

Office manager James F. Kane sat at his street-side desk in the northeast corner, forms spread before him and a fountain pen in hand, trying to explain a billing change to a frustrated customer. Like many New Yorkers that third Monday in May, Kane had hoped to get off work with enough energy to take the wife out to Flushing and the newly opened World’s Fair. Lately all the major dailies, most prominently the New York Times and the Herald Tribune, had devoted pages and pages to scheduled events and detailed stories about the many exhibits. The publicity was working, and the whole city was abuzz. None other than First Lady Eleanor Roosevelt was being honored at a luncheon that very day, her appearance putting the presidential imprimatur on the event. The busy First Lady still had time to write a popular syndicated column, “My Day,” which was a must-read for any conscientious hostess. If she could make time for the fair, certainly anyone else could. Kane likely hated to disappoint his wife, but the increasingly baffled customer at his desk was wearing him down. All of a sudden, an evening at a damp, crowded fairground probably seemed more of a chore than a stirring night out.

From the Hardcover edition.

Meet the Author

David Goewey was born and raised in Ossining, New York, the grandson, son, and brother of Sing Sing officers. He lives in New York City.

From the Hardcover edition.

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