Long Island Interlude: Love at the Jailhouse

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Mineola, N.Y., sometime in November 1913 (about seven months before the death of Lulu Bailey).

Sanford Gwynn woke up in the drainage ditch behind the Nassau County Jail early on a November morning. In a matter of moments, he would nominally be witness to the full flowering of one of the more lurid criminal enterprises in Mineola’s history.
For his part, Mr. Gwynn was too hung over to really notice.

The parking lot to the jail was a tangle of cars and activity, and all of it was clearly visible from where Mr. Gwynn was sprawled. Women in flirty, airy dresses made too-familiar gestures to men in disheveled suits. Most of the men were leaving, some of them with half-empty bottles, all of them with half-satisfied smirks on their faces. A handful, though, were late arriving, or were returning for a second pass through the most popular brothel and gaming house in all of western Long Island: That which was operated by Warden Winfield S. Box.

Mr. Box was not merely a pimp; at least, this is what he told himself. In any event, he was a respected, churchgoing citizen, with a wife and a large, pleasant-looking family. He was well-known for his prowess at horseshoes and well-liked at the Elks lodge that met just a few blocks away. To a fault, though, he also was an eminently practical man and, for reasons which will soon be clear, although probably not to Mr. Gwynn, organizing a whorehouse and casino in the county jail seemed like the natural thing to do.

At that moment, and not unusually, Mr. Gwynn was remarking foggily to himself that there was nothing wrong with waking up in the ditch.

He had come to realize, after a long period of continual observation, that there was a great comfort to it — if you allowed first that every ounce of his being was being savaged by a ruthless and unrelenting hangover.

In the first place, it was always cool in the ditch.

Even in the hottest days of August, the grass there was long and lush, and black walnut trees lolled their branches protectively overhead. The earth, soft and forgiving, would nuzzle a prone body like a concerned parent. In the spring or the fall, the early morning would bring dew, which to Mr. Gwynn held a soothing, almost icy, dampness that would apply itself to every inch of his nervous, twitching body.
In the second place, the ditch was convenient.

Straight behind Mr. Gwynn, about 100 yards away perpendicular from the ditch, was Ali Kafeer’s luncheonette. Immediately across the ditch was the aforementioned parking lot of the county jail, where Mr. Gwynn was a regular visitor. About 200 yards farther in the same direction was Pedersen’s Ale House, where he was also a regular. North of him, where the ditch met Packwood Road, was the Bengal Club, where he was regularly turned away. And not far to the south, somewhere beyond the trees, was the back door to the morose row house where he had a room.

The ditch was secluded, too.

It wound through a tall, disorganized grove of pitch pines, spruces, walnuts and other trees like a scar on the back of an angry, dirty animal. Below this wild mesh was a riot of shrubs — juniper, holly, bayberry — and harder-to-identify plants. Lapping at the roots, blanketing the mud, were mounds and mounds of rotting leaves, twigs and trash of all kinds. Here and there in the small wilderness were discarded monuments to carelessness, like the cast-iron stove that had been improbably tossed nearby.

The ditch itself was probably the result of the construction of the jail. Though, if had been an honest man, Mr. Gwynn would confess that in all the time he spent in the ditch, he never once wondered how it got there.

It should be said that Mr. Gwynn was not a honest man.

On this particular morning, in early November, the dew might have been frost. But it wasn’t, and Mr. Gwynn laid in the grass with his eyes closed, mostly oblivious to the occasional shrieks of playful laughter at the jail, and felt the coolness of his wet clothes with a perverse satisfaction. As car doors slammed and engines revved below him, he slowly stretched his limbs out.

Without opening his eyes, he knew his face was flecked with blades of grass and drops of muddy water. He could feel that his clothes were about half-soaked, and not only with water. He sighed. He did not mind.

As a breeze passed over his face, Mr. Gwynn slowly formed a mental sketch of the night before. He had left the offices of The Mineola Press Boy and Gazeteer after the close of the afternoon edition, had a dinner of eggs and toast under the obsequious gaze of Mr. Kafeer and then tried in vain for half an hour to get inside the Bengal Club.

At length, he had procured a bottle of rye from a corner store and wandered around in the gloaming trying to look casual while drinking it. Eventually, he fell into Pedersen’s, where he was sure he had told several fascinating anecdotes to a coterie of attractive young women.

As he laid there, the sky still dark and blank and the wind gently nudging the trash around his head, he thought he could hear their joyful adulation.

“Oh, Mr. Gwynn,” they said. “Your sense of humor!”

They all laughed, not just the girls but the whole bar. A chorus of admirers tumbled into snorts and heehaws. Even the band stopped playing. Swells of cheering overwhelmed him, men slapped him on the back, and mugs of beer sloshed behind him on the bar.

And by now, Mr. Gwynn was sure he could hear that laughter, for real.

He lifted his head, gingerly, and stared down past his feet at the jail. At first, all he noticed was that he was wearing only one shoe. A moment later, his red, swollen eyes focused in surprise on the denouement of another night of the warden’s debauch.

And the instant that Mr. Gwynn began to question why so much was going on in the parking lot of the county jail at 5 in the morning, his excesses from the previous evening welled up like an orchestra and gripped his head and his stomach in a simultaneous convulsion of pain, nausea and temporary blindness.

Had he been in a contemplative mood, he might have mentally added to his list of reasons why the ditch made a perfect early morning haven: No one cares if you throw up. In fact, reasonable, respectable people would tell him, Yes, yes, by all means. Go to the ditch over there and throw up.

But he wasn’t thinking about any of that. He just turned his head and vomited. His view of the parking lot shifted to dark green grass and then faded away altogether to white and then red.

He let his head slap mercifully back into the cool November mud.