Editor’s Note: This is Part One of Phil’s three-part saga about his days driving an illegal taxi [otherwise known as a “gypsy cab”] on the streets of New York City back in the late 1960s when he was still just a teen. 

“When a man has nothing left, he can always sell his cohones.” – Ernest Hemingway

The Origin of Gypsy Cabs

During the early 1930’s, anyone could pay the city $10 for a taxi medallion to register their vehicle for livery service. The small silver shield, attached to the hood of their car, documented drivers were licensed to transport passengers who hailed them on the street. As the job market crashed during the Great Depression, increasing numbers of desperate people invested $10 for the opportunity to cruise the streets in hope of a few fares to pay for gas with enough left over to feed their families for a day. The number of cabs soon outweighed customer demand.

On March 1 1937, the New York City Board of Aldermen passed the Haas Act, prohibiting the sale of new medallions until the depression ended. But there was an unexpected consequence when the New Deal and subsequent war boom re-ignited the economy. The existing 11,787 medallions became the best investment in America, skyrocketing in value from $10,000 during the 1940s—to $30,000 by the late 1960s. Politicians, on behalf of their business allies, successfully short-circuited the second half of the Haas Act. New medallions were never issued.

As demand for quick transportation outpaced supply, taxi drivers had the luxury of remaining in business districts and affluent neighborhoods, enjoying the highest profits with the least risk. Residents of poverty stricken neighborhoods, already under-serviced by bus and subway systems, had limited access to livery service. They would stand at bus stops during the night for over an hour, praying for a cab to hail, fearing the same crime and violence that deterred taxi drivers.

There were a few car services legally permitted to take phone calls and dispatch drivers. But as the transportation crisis worsened in Black neighborhoods, enterprising operators realized there was far more money to be made searching the streets for an eager but neglected clientele. Thus was born the gypsy cab.

Privateers soon began roaming these neighborhoods. A yellow Christmas light placed in the right corner of a windshield or hood was all it took to designate a gypsy cab. Some worked for a growing number of car services, while others were simply independent hustlers. While every street fare was illegal, these drivers provided an essential service to communities that scared the police department’s Hack Squad (taxi enforcement division), as much as it did legitimate cab drivers.

Down and Out in New York

I left home when I was sixteen with a thirst for adventure looking forward—and an absence of fond memories looking back. It was 1967 in New York City.

A year later, I was living with my girlfriend Irene in a tenement apartment on 10th street between Avenues A and B.  The Lower East Side had the worst crime statistics of any neighborhood in America. I’d been out of work for two months, was flat broke and frantically reading the want ads when I came across one that said: Drivers Wanted. No experience necessary. $30 per day. That was decent money back then. The timing was perfect, too, as I’d recently tricked the motor vehicle bureau into issuing me a chauffeur’s license, despite being underage.

Early the next morning, I drove my old black Studebaker over the 59th Street Bridge to the Long Island City address. I walked into the greasy, back street, industrial slum garage, past mechanics working on cars, into a small side office with an overweight man sitting behind a desk. About a dozen other men stood around just inside the doorway, hooting and joking as men will do in an industrial setting. One of them was boasting of his sexual exploits at a recent party when an obese gentleman in a sleeveless T-shirt cut in with a profane remark. The group tumbled upon itself with arm punches and howling laughter as if this were the most amusing thing they’d ever heard. Eventually, the man at the desk noticed me and asked, “What do you want, kid?”

Explaining that I was responding to the ad, he asked to see my driver’s license. I silently willed for him to not calculate from my birth date that I was underage, and he didn’t. I was given forms to fill out, led back into the garage, and told to sit in a blue Checker car. A few minutes later, I was joined by a man who drove me around for ten minutes, showed me how to work the meter and two-way radio, explaining various code numbers used as shorthand when communicating with dispatchers. “Now, go out in the street and make some money,” he said as I dropped him off at the garage.

Still uncertain of my actual job description, I spent the next few days driving up and down main thoroughfares in the best neighborhoods, constantly on the radio asking if there were any calls for me, occasionally getting one, and responding to hails from the street. I worked every day from 5 a.m. to 5 p.m., coming away with about $20 dollars per shift. It wasn’t much per hour but considering I’d been unemployed for two months and survived the winter in a torn denim jacket, it felt like a lot of money. One morning, I brought the vehicle back home to show Irene. She looked out the window and said, “Oh, that’s a gypsy cab.”

As time passed, I began wondering why everyone else was making twice as much as me. I finally asked a friendly coworker who responded, “The money’s in the ghetto. Most of the calls are in South Jamaica.” I started working there and my earnings rose to $30 dollars per shift; still not comparable to other drivers who’d grown up in the neighborhood and didn’t lose time getting lost on dead end streets and broken down roads, but at least the ad was now fulfilling its promise and I was starting to enjoy the hustle.

There was always talk at the garage about robberies but I wasn’t overly concerned working the day shift. I rode around with my doors unlocked, accepting anyone who wanted a ride, radio or not.

One evening, I picked up a young mother with a toddler and two men who lived with them. We drove through Jamaica trying to find a supermarket willing to cash her welfare check. Every time she left the cab, one of the men would start torturing the three-year-old. He took out a magic marker, drew all over the boy’s laughing face, and then suddenly changed his demeanor. “Why you make your face such a mess? I’m gonna burn you!” He took out a cigarette lighter, lit the flame, and naturally, the terrified child started crying.

On another occasion, the child was told he was no longer wanted and to leave the cab. When threatened again with burning, the boy opened the door and started running. His tormentor pursued him, screaming, “What do you think you’re doing, running away?!” He picked up the screaming child and twirled him violently overhead. By the time his mother returned, the tears had nearly dried.

It felt pointless to intervene with this bizarre, dysfunctional family. Lecturing them about children’s rights wouldn’t have changed who they were, but might have gotten me killed. In retrospect, I should have calmly radioed the dispatcher to provide my location, slipping in the code 007, which meant police assistance needed. But it never occurred to me at the time because I’d only experienced law enforcement as persecutors to be avoided.

Unable to cash the check, the group politely bid me good evening, paid the $3.50 fare and departed. I drove back to the garage contemplating a gruesome demonstration of how psychotics and sociopaths were born and bred in our society.

I’d avoided working nights, but one day ended up using the cab to chauffeur Irene around on errands and worked the late shift to make it up. I was terrified but nothing bad happened and the earnings were sensational. Since I was inherently nocturnal by nature, I wound up transferring to nights.

Two burly dispatchers, Big Mike and Big Mel, alternated between day and night shifts. Late one night I received a radio call:

“Pick it up 15, pick it up 15!” Big Mike hollered over the radio static.

“Yeah, yeah, this is 15!  15 here!” I responded, referring to my car number.

“What’s your 20 mister? What’s your 20 (location)?”

“I’m at Liberty and one-six-two, my friend.”

“10-4. You go to Archie’s and pick up Joey.” Big Mike was referring to a notorious after-hours club, situated in an inconspicuous old house on Sutphin Boulevard, offering gambling and prostitutes to the community. Several drivers I knew had been robbed by its patrons.

Following a few minutes of driving 45 mph down side streets, through yellow lights and swerving around pot holes, I was back on the radio, “Car 15 here, pick it up mister. Pick it up! I’m 10-30 (arrived at location).”

“Wait in the driveway for Joey. He’s going to the Bronx. Lot of MFC (motherfucking cash) on this one.”

“Ten-fo”

Over time, I became frustrated with the radio. Half a dozen cars were always competing to get through the static and the most lucrative rides were often reserved for the dispatcher’s friends. I began shutting off the radio and hustling what I could on my own.

I continued to get lost in the maze of back streets and housing projects, and was becoming intrigued with the idea of going into midtown Manhattan and trying to pass myself off as a regular taxi. (It would be some time before all medallion cabs were required to be yellow.)

One Friday night, I put my fantasy to the test and the money kept rolling in. When I returned to the garage with my trip card, Big Mike looked at me and said, “Hey kid, you’re really rolling tonight, huh!” I’d made my bones in the game and graduated to the flat rate system, paying $21.50 per night for the cab and keeping the rest.

Midtown Manhattan became my new stomping grounds. There was clearly more business here per square foot than any other part of the city. But I had to remain constantly on the alert for the Hack Squad and more importantly, predatory medallion taxis. It was part of their culture to blame all misfortune in their lives on gypsy cabs. This wasn’t an organic bias. The fleet owners’ trade publication featured a lurid anti-gypsy expose on every front page, condemning us for limiting the ability of honest drivers to earn a living. It’s relatively easy to channel the aggression of people engaged in tedious and dangerous employment.

It was ironic because we actually made their lives more profitable and far safer. The New York City livery statutes deemed it illegal for legitimate cabs to bypass a hailing passenger or refuse a ride. But there was minimal enforcement because gypsies provided an alternative. I often observed ten cabs drive past a hailing Black person headed uptown, before stopping and offering service to the frustrated person. We kept the medallions out of neighborhoods they feared. But logic never serves to outweigh emotion.

I had my first encounter with them several nights after venturing into their territory. I stopped to pick up someone hailing on Lexington Avenue amid four empty medallion cabs. They surrounded me from all sides and exited their vehicles. A man telling his colleagues “let me hit him first” opened my door screaming, “Get the hell out of that cab!!”

I pulled the door shut and executed the most remarkable driving maneuver in the history of New York.  I backed up through a red light, jammed the car into forward, and ran the light again, making a hard left from the far right lane onto 52nd Street, as one of the drivers put his fist through my side view mirror. I was impressed with how my passenger kept his cool and later offered him a free ride. Afterwards, I learned to be more vigilant and always keep my doors locked.

One night, after narrowly avoiding a similar confrontation, I picked up a man going to East Harlem who turned out to be a fellow gypsy cab driver. “Sure, they’re gonna fuck with you if you drive downtown,” he told me. “The money’s here, uptown, anyway, and they won’t fuck with you.”

I began working Harlem and the South Bronx, learning the best streets to hustle, along with bars and after-hours joints where I could pick up drunks and hookers late at night. I was aware my skin color and long hair made me appear out-of-place and an easy target. But folks sensed I wasn’t some middle-class college kid, had paid my dues on the street, and tended to like me and respect what I was doing. Of course, there were always exceptions out there stalking the streets.

“One of these days, you’re gonna get a 007 ain’t nobody gonna be able to help you with,” Big Mike told me one morning. But I was wild, had found my groove, and felt immortal.

These were the days when the majority of street violence involved switch blade knives, rather than guns. I kept a crowbar beside me, because it had more striking distance than a blade. I developed one precautionary rule, however: Never pick up more than one young punk at a time, unless they were accompanied by girls. I figured stoned-out folks with beautiful dates had better things to do than jack me. People sensed I was a good listener who understood hard times, and everyone from prostitutes to criminals poured out their life stories as we drove through the night.

One evening when I reported for work, Big Mel offered me an opportunity to step up to the next level: rent a cab 24-7 for $168 per week. It felt like an irresistible chance to earn some real money. The taxi could also be my personal vehicle and I wouldn’t have to travel to and from the garage each night. I was assigned car 29.

I’d just turned eighteen and felt like a man, bringing home $200 per week (equivalent to $1,000 today) and supporting my girlfriend. But the pressure of working every night with the possibility of being killed or busted started building, along with serious sleep deprivation. I lived an active life during the day and averaged forty hours before getting some rest.

I ended a long night racing down the Grand Central Parkway through an early morning shower, suddenly lost control rounding a curve, and found myself hydroplaning full speed at a forty-five degree angle across highway lanes toward a field of grass. The steering wheel was spinning wildly as the car headed straight toward a lamppost. All I could do was sit and scream, “NO! NO! NO!” as the metal column rushed up on me. A moment before impact, the cab miraculously skidded left around the obstacle and came to an abrupt stop about forty yards into the pasture, surrounded by a pack of curious dogs. I sat there shaking for ten minutes before heading home.

Several days later, I came down with strep throat and the taxi sat idle. My nerves were shot. I was too wired to sleep and fought constantly with Irene. I returned the vehicle to Big Mel, owing several days rent, and swore I’d never drive gypsy cabs again…

Click here for PART II:  There’s Always Action in Jamaica