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

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9781400054695: Crash Out: The True Tale of a Hell's Kitchen Kid and the Bloodiest Escape in Sing Sing History

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.

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About 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.

Excerpt. Reprinted by permission. All rights reserved.:

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 i...

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