The Jeffrey Hillman I Knew Had Shoes But Still Needed Help

I met Jeffrey Hillman, the homeless man now standing barefoot at the center of a media flurry, in the spring of 2008. Freshly paroled from Columbia Law School, I sublet an apartment on 72nd and Columbus so I could study for the bar exam in the Jerusalem of yuppiedom, Manhattan's Upper West Side. My girlfriend and I loved the lifestyle, which New York Times columnist David Brooks described so elegantly as Bohemian Bourgeoisie. For us, this meant going to price-gouging farmer's markets, lectures at the JCC, and yes, even the occasional trip to Magnolia Cupcakes. One particularly gorgeous summer evening, we strolled over to what I've long considered New York's most overrated cupcake store - during which I probably subjected my poor girlfriend to a treatise on frosting texture.

He wasn't so much standing as he was stooped over, the man's six-plus-foot frame nearly reduced to my Hobbitine height. The guy probably weighed the same as I did, fattened up in years prior by trillion-dollar law firms and their butter-laden free dinners. Literally with hat in hand, he stepped forward and asked for anything I could spare. "Sorry," I said with routine coolness as I brushed by.

I wasn't working as a lawyer any more, and my modest salary from The Truth About Cars - for which I was still working as the Managing Editor - didn't give me the freedom to subsidize the entire 40,000-person homeless population of New York. The utility of this, my usual cop-out, dissolved a few seconds later, and Jessica and I returned.

"Jeffrey," he said when I introduced myself and asked his name. "Can we get you anything?" I nodded toward the cupcake emporium, a shop whose Disneyland antebellum décor only now struck me as odd. Jeffrey wanted bread pudding, a dessert dense in the calories he desperately needed.

After delivery, we chatted a minute more and parted ways. He was, in fact, wearing shoes.

During the next four months, I ran into Jeffrey everywhere. In front of the artisanal bread bakery on 72nd. Outside the copy shop on Broadway. By the parking garage at 73rd and Amsterdam. His world was outside these stores; mine was within them. Still, this didn't stop Jeffrey and I from talking, nearly every day. We'd make small talk. He'd recount a recent movie he saw on a bootleg DVD while crashing with a friend. I filled him in on where I grew up. We ate hot dogs at Gray's Papaya, where the open storefront meant we were both inside and out.

In the past four years, it's remarkable how much of my time with Jeffrey I remember. I've forgotten where he grew up, or what he did before he was homeless. I know he had served in the army, making him one of the hundreds of thousands of homeless veterans in the U.S. Jeffrey had already been on the street for several years when we met in 2008, and assuming he has been sleeping rough since then, that makes at least a decade that this man has been without a home.

Coming out of a bar one night, I heard "Justin!" and was greeted by Jeffrey, wearing a smile. We had a snack. Jeffrey asked if I could swipe him into the subway so he could sleep on a bench, out of the rain. "I don't have a MetroCard," holding back that I didn't need to take the subway that week because I was driving a Bentley, which the company had loaned to me for free. "And I'm out of cash," I said, with a phrase that means wildly different things to the two of us. "I wish I had known before we spent it on food, then," Jeffrey reflected, looking at the sidewalk.

For the homeless, the pavement is home. I ran to the ATM.

I moved out of the neighborhood on an incredibly humid night in August after a talk with the police. That night, I set the record for my own stupidity, spending a tense four seconds reviewing the criminal law portion of my bar studying while waiting for the air conditioner I dropped out of a window to hit the ground. After it exploded at the bottom of the airshaft ten stories below, I questioned my atheism and considered my fortune at being only moderately fucked. The cops in the Crown Vic I flagged down in front of the apartment building had little interest in my first-world screw-up after finding out that nobody was-or really could have been-hurt. Pavement, for me, is how one demolishes a window AC unit.

And so it's the same kind of concrete that was under Jeffrey's shoeless, calloused feet last week when Officer Lawrence DePrimo bought him a pair of boots. The photo a tourist took of the scene and posted online has become a sensation, a Chicken Soup for the Instagram Soul this holiday season. I didn't know it was in fact Jeffrey in that picture until the New York Times published a follow-up story this morning, having spoken with Jeffrey and finding him barefoot once again.

"Holy shit," I said aloud, seeing the article's accompanying photo. "It's Jeffrey. I'm so relieved he's still alive." I'd like to think I know what Officer DePrimo felt, because I too saw the warmth in Jeffrey Hillman's weather-worn face.

Jeffrey told the Times he had to hide his new footwear because it's too dangerous to wear an expensive set of boots. He's barefoot again. That this is reality is unacceptable lunacy. I'll be making a sizeable donation to the annual coat drive from New York Cares. Join me, or pick a charitable organization of your own. Sidewalks and streets are for shoe and tire rubber, not bare skin.


Justin Berkowitz is the East Coast Bureau Chief for Car And Driver.

Photo Credit: AP