The Last Medallion: A New York Taxi Story

Part 1: “An Oracle on Wheels”: My Grandfather’s New York

Michael’s grandfather, Leo, used to say that to drive a cab in New York after the war was to hold the city’s heart in your hands. His stories, told over Sunday dinners that smelled of garlic and simmering tomato sauce, were not of fares and figures, but of a city roaring back to life, a symphony of horns and humanity he conducted from behind the wheel of his Checker. Leo’s New York was a world forged in the crucible of the Great Depression, an era that had nearly destroyed the taxi trade. He spoke of the “wildcat” days before 1935, an unregulated free-for-all where thousands of desperate men in their own cars fought for scraps, driving fares and standards into the ground.¹ Widespread poverty had shrunk demand, while a surplus of drivers—many of them unemployed men with a car and nothing to lose—created a “fierce competition for customers”.¹ The situation was untenable, a race to the bottom that threatened both public safety and the drivers’ ability to make a living.²

The Dawn of the Modern Cab

The change, when it came, was seismic. In 1937, responding to calls for reform, New York City’s Board of Aldermen passed the Haas Act, a piece of legislation that would define the industry for the next 80 years.¹ It created the medallion system, a licensing scheme that capped the number of taxicabs, bringing supply in line with public demand.³ The chaos of the “wildcat” era subsided, replaced by a newfound stability. For a one-time fee of $10, a driver like Leo was granted the right to operate, a right that suddenly had structure and value.¹

This regulatory framework, born from a crisis of “too many cabs… chasing too few passengers,” was intended to bring order, not to create a new class of asset.⁶ Yet, by making the medallion a transferable permit, the city inadvertently planted the seeds of a future speculative bubble. The logic was simple and, at first, benign. A medallion was a license to work. But if that license was limited in number and could be sold to someone else, it ceased to be just a license. It became a piece of property, an asset whose value was tied not just to the work it enabled, but to its own scarcity. This fundamental shift was the system’s original sin. The evidence of this transformation appeared quickly. While the initial purpose was to stabilize driver income, license holders soon realized they held a tradable commodity, “somewhat like real estate”.¹ The $10 license of 1937 was, by 1950, trading for an average of $5,000.¹ This was not mere inflation; it was the birth of a market, the moment a tool for labor began its long, slow metamorphosis into a financial instrument.

The Post-War Boom and the Iconic Cab

The stability brought by the Haas Act laid the foundation for what Leo called the golden years. The Second World War, with its rationing of fuel and car parts, pushed countless New Yorkers into taxis, creating a surge in demand that eliminated the need for drivers to fight over fares.¹ The post-war economic boom sustained this prosperity. It was in this era that the American taxi cemented its cultural identity. The vehicle of choice was the Checker taxicab, a machine built like a tank but with a passenger cabin spacious enough for a family. These cars, with their distinctive checkerboard stripes, became synonymous with the city itself, an iconic part of vintage New York history.¹

Leo took immense pride in his Checker. It was his office, his connection to the city’s pulse. He was part of a new generation of drivers—which, after the war, included more women and African Americans—who were reshaping the profession’s image.¹

The Driver as Cultural Figure

The perception of the cabdriver underwent a profound transformation. No longer seen as a “person of dubious character,” the New York hack became a trusted fixture of the urban landscape.¹ As Professor Graham Russell Gao Hodges wrote, the driver was now “an oracle, a counselor, a philosopher and an almanac”.¹ This romanticized image was amplified by countless movies and radio shows, which portrayed cabbies as gritty, hardworking heroes who knew every shortcut and every secret the city held.³ They were the men who returned lost wallets stuffed with cash, who helped deliver babies in the back seat on the way to the hospital, who could offer a piece of advice on anything from a ball game to a broken heart. For Leo, and for Michael listening to his stories, this wasn’t just a job. It was a respected vocation, a vital thread in the city’s rich tapestry.

Part 2: The Gilded Cage: How a $10 License Became a Million-Dollar Trap

Michael’s father, Sal, inherited Leo’s love for the job but not his luck with timing. When Sal bought the family’s first medallion in the 1980s, the world had changed. The medallion was no longer a simple $10 license; it was a serious investment, costing him nearly $100,000.⁸ Yet, it seemed like the safest bet in the world. The city hadn’t issued a significant number of new medallions in decades—going 60 years at one point without a single new issuance—creating a market of extreme artificial scarcity.⁶ This scarcity, coupled with the medallion’s status as a tangible asset, fueled a relentless appreciation in value.

The Asset Inflates

Throughout Michael’s childhood, the medallion was the silent, appreciating member of the family. Its value became a benchmark of their success. Sal watched as the price climbed steadily: from around $125,000 in 1990 to $280,000 in 2004, then accelerating to $600,000 by 2010.⁶ By the time Michael was ready to join the family business, the market was white-hot. Medallions were considered a better investment than U.S. housing or even gold.¹⁰ They were a “bulletproof investment,” a ticket to middle-class security in a city of dizzying costs.

The system had evolved into something its creators never intended. It became a mechanism that extracted wealth from the labor of drivers and funneled it toward a class of non-driving investors, fleet owners, and financiers. With a fixed number of medallions and a “huge supply of drivers competing to lease them,” the power dynamic shifted decisively.⁶ Most medallions were no longer owned by the people who drove the cabs but by investment companies and large fleets.⁹ For a driver without the capital to buy, the only option was to lease a medallion for a punishing daily or weekly fee. This lease payment, which had to be covered before a driver could earn a single dollar for themselves, cut directly into their income while simultaneously raising costs for passengers.⁹ The government-enforced scarcity, designed to protect workers, had created a perverse form of feudalism. The driver performed all the labor, bore all the risk of a slow day, and paid for the gas, but the financial benefit of the market protection—the “surplus price from limited competition”—flowed directly to the owner of the asset.¹¹ It was a regressive tax on labor, paid every single shift.

The American Dream, Leveraged

In 2012, swept up in the frenzy, Michael made the decision that would define his life. He took out a massive loan to purchase a second medallion for the family, paying just over $1.2 million.⁴ It felt like the ultimate validation of his family’s hard work. He was securing his future, just as his father and grandfather had. He was not alone. For thousands of drivers, many of them immigrants, the medallion was the physical embodiment of the American Dream. They refinanced their appreciating medallions to buy homes, pay for their children’s college educations, and build a stable life.¹³ The loans were easy to get; the value, it seemed, could only go up. The total value of all medallions in New York City was estimated at a staggering $16.6 billion in 2013.⁶

The Predators and the System

Beneath the surface of this booming market, however, a more sinister dynamic was at play. A New York Times investigation later revealed that some lenders and credit unions had engaged in predatory practices, knowingly financing medallion purchases at inflated, above-market prices and trapping drivers in risky loans with balloon payments they could never hope to repay.⁹ This was compounded by a culture of “cronyism” in which large, wealthy fleet owners made substantial donations to local politicians. “Coincidentally,” the subject of issuing new medallions to satisfy the city’s growing demand for cabs and stabilize prices never became a serious topic of discussion.⁵ The system was a gilded cage, and the door was about to slam shut.

The following table illustrates the sheer scale of the medallion bubble and its subsequent collapse, demonstrating that this was not a uniquely New York phenomenon but a systemic failure across major American cities that had adopted a similar regulatory model.

Table 1: The Rise and Fall of the Taxi Medallion: A Tale of Four Cities

City	Peak Value (Year)	Trough Value (Year)	Percentage Decline
New York City, NY	> $1,000,000 (2013)	~$136,000 (2019)	~86%
Boston, MA	~$700,000 (2014)	~$40,000 (2018)	~94%
Chicago, IL	~$385,000 (2012)	~$30,000 (2018)	~92%
Philadelphia, PA	~$80,000 (2005)	~$50,000 (2018)	~38%

Source: Data compiled from.⁶

Part 3: The Ghost in the Machine: The Unraveling

The first sign of trouble was subtle. In 2011, a new black car service called Uber arrived in New York.¹² At first, it was a niche luxury service, barely a blip on the radar of a yellow cab driver like Michael. But it was the start of what one observer would later call a “shock-and-awe campaign”.¹⁴ Uber and, soon after, Lyft, didn’t just enter the market; they invaded it.

The “Shock-and-Awe” Campaign

Michael watched as the city’s streets were flooded with new vehicles. His world was governed by the hard cap of 13,587 medallions, a number that had barely budged in his lifetime.⁹ Suddenly, he was competing against an army. By 2017, there were over 50,000 for-hire vehicles affiliated with rideshare apps on the road, all summoned by a smartphone.¹⁵ These companies operated in a regulatory gray area, pushing “the envelope with municipal and state regulators, in many instances, blatantly disregarding local laws”.¹⁴ While Michael had to maintain a specific vehicle, pass rigorous inspections, and carry commercial insurance, rideshare drivers could use their personal cars with far less oversight. The barrier to entry, once a million-dollar medallion, was now a $550 city license and a background check.¹⁵

The Vanishing Hail

The change was visceral. Cruising down Seventh Avenue, a stretch that once guaranteed a fare in minutes, became an exercise in frustration. The sea of hands that used to wave from the curb was gone. In their place were people staring intently at their phones, waiting for a different car, a ghost in the machine that he couldn’t see but could feel everywhere. The data confirmed his experience. Between 2015 and 2017, the number of monthly trips by services like Uber and Lyft in New York City jumped from 2.6 million to 9 million. Over the same period, yellow cab rides declined by more than two million per month.¹⁵ Studies in other cities showed similar devastation; in Los Angeles, the taxi industry lost $17.1 million in revenue in 2014 alone as trips plummeted by nearly 18%.¹⁶ The profitability of the entire industry was collapsing.¹⁷

The Human Cost

Then the floor fell out of the medallion market. The “bulletproof investment” was worthless. Prices crashed from over $1 million in 2013 to around $650,000 in 2015, and then kept falling, hitting a low of $136,000 at auction in 2019.⁶ Michael was catastrophically underwater on his loan. He owed a bank a million dollars for an asset he couldn’t sell for a tenth of that price.

His story was repeated thousands of times over. Drivers who had leveraged their homes and life savings were facing foreclosure and bankruptcy.⁶ The financial strain became a mental health crisis. In 2018, a string of high-profile driver suicides cast a dark shadow over the industry, a tragic testament to the human cost of the collapse.⁸ The COVID-19 pandemic only amplified the despair, cratering what little ridership remained.¹³ Some lenders and credit unions, recognizing the crisis, worked to restructure loans. But others were relentless. Fleet owners like OSK, which had bought up distressed medallion loans, dispatched repo men to seize the devalued assets from drivers who fell behind on payments they could no longer afford.¹³

Why They Won

In the quiet hours of his empty cab, Michael was forced to confront a painful question: Why was his industry so fragile? Why did it crumble so quickly? He had to admit it wasn’t just about a better app. The taxi industry had been complacent, protected for too long by its monopoly. Service could be unreliable, with dispatchers who never sent a car and drivers who refused fares to the outer boroughs.¹⁸ There was a perceived lack of accountability; a bad ride in a taxi was something you complained about to your friends, but a bad ride with Uber was reflected in a one-star rating that could get a driver kicked off the platform.¹⁵

The disruption was as much psychological as it was technological. Ridesharing didn’t just introduce a more convenient technology; it broke the dysfunctional psychological contract that taxis had with the public. Decades of consumer frustration—from fare-gouging and reckless driving to dirty cars and a general lack of “accountability, trustworthiness, and transparency”—had created a deep well of resentment.¹⁹ Uber and Lyft succeeded not just because they offered a slick, data-driven platform with real-time tracking, cashless payment, and upfront pricing, but because they offered an alternative to a system that many felt had stopped serving them long ago.²¹ The public’s enthusiastic adoption of ridesharing was as much a vote

against the old system’s flaws as it was a vote for the new one’s features.

The following table provides a systematic breakdown of the fundamental operational and economic differences that gave ridesharing a decisive advantage over the traditional taxi model.

Table 2: The Old vs. The New: A Comparative Analysis of Taxi and Rideshare Business Models

Feature	Traditional Taxi Company	Rideshare TNC (e.g., Uber/Lyft)
Regulation	Highly regulated; fixed number of medallions/licenses creates artificial scarcity.	Minimal regulation; operated in legal gray areas, leading to an uncapped supply of vehicles.
Driver Status	Employees or, more commonly, independent lessees paying fixed daily/weekly fees.	Independent contractors (“gig workers”) paying a percentage-based commission on each fare.
Pricing Model	Regulated meter fares; fixed rates with no flexibility for demand.	Dynamic “surge” pricing that adjusts fares based on real-time supply and demand.
Technology/Dispatch	Street hails or phone calls to a central dispatcher; limited tracking or payment options.	App-based platform with GPS tracking, automated dispatch, cashless payments, and two-way ratings.
Vehicle Ownership	Company-owned fleets or driver-owned vehicles meeting strict specifications.	Drivers use their own personal vehicles with less stringent requirements.
Market Entry Barrier	Extremely high; cost of purchasing or leasing a medallion often reached hundreds of thousands of dollars.	Extremely low; minimal cost for licenses and background checks.
Service Customization	Standardized service; limited vehicle choice or ability to pre-schedule with a specific driver.	Multiple service tiers (e.g., Pool, X, Black), ride scheduling, and driver/rider matching.

Source: Data compiled from.⁹

Part 4: The Crossroads: Lessons from the Bookseller and the Brewer

For months, Michael’s response was a cocktail of anger and denial. He joined protests outside City Hall, his voice hoarse from chanting slogans demanding a cap on rideshare vehicles.¹⁵ He and other medallion owners lobbied politicians, arguing that the city had betrayed them by allowing an unregulated competitor to destroy the value of the very licenses the city itself had sold. But deep down, he knew these were the desperate tactics of a losing army. He was fighting a defensive war on his competitor’s home turf—price and on-demand convenience—and it was a war of attrition he could not win.

The shift began one afternoon at the public library, where he stumbled upon a magazine article. It wasn’t about taxis; it was about the unlikely resurgence of independent bookstores.

The Bookstore’s Playbook

Michael read about how Amazon’s arrival in 1995, with its endless inventory and predatory pricing, was supposed to have been the death knell for local bookshops. Between 1995 and 2000, the number of independent bookstores in the U.S. plummeted by 43%.²³ Yet, after hitting a low in 2009, they began to grow again. They hadn’t tried to become a smaller, less efficient version of Amazon. They had changed the game entirely, focusing on a strategy that analysts dubbed the “3 C’s”: Community, Curation, and Convening.²³

A light went on in Michael’s mind.

• Community: The bookstores had fostered a powerful sense of localism, convincing customers that shopping there was an investment in their own neighborhood.²³ Michael looked at his yellow cab—it wasn’t just a car; it was a New York icon. His decades of experience weren’t just a skill; they were a community asset.
• Curation: Bookstores couldn’t compete with Amazon’s massive warehouse, so they stopped trying. Instead, they offered carefully curated selections, tailored to local tastes. Their knowledgeable staff practiced “handselling”—offering personalized, expert recommendations that no algorithm could match.²³ Michael realized he couldn’t compete with Uber’s sheer number of cars, but he could offer a curated, premium
  experience.
• Convening: The bookstores transformed themselves from simple retail spaces into “third places”—community hubs that hosted author readings, book clubs, and children’s story hours.²³ They gave people a reason to come beyond just buying a book. Michael began to see a path where he could be more than just a ride from point A to point B. He could be a trusted transportation partner for specific events, businesses, and clients who valued reliability over rock-bottom prices.

The Brewer’s Blueprint

His thinking crystallized during a visit to a local craft brewery in Brooklyn. The place was packed. As he sipped a rich, flavorful stout, he observed their business model. It was another industry dominated by massive, global corporations, yet this small operation was thriving. He saw direct parallels to the bookstore’s strategy.

• Quality over Volume: The brewery wasn’t trying to compete with the economies of scale of global beer companies. It was emphasizing flavor, innovation, and quality—winning over customers with a superior product, not a cheaper one.²⁵ Michael knew his service had to be about quality: a meticulously clean car, a professional and courteous driver, and ironclad reliability.
• The “Tasting Room” Experience: The brewery wasn’t just a factory; it was a destination. The lively taproom, with its events and communal tables, built a direct relationship with customers and fostered a loyal following.²⁶ This reinforced Michael’s nascent idea: his cab had to offer a superior customer experience that built a direct, trust-based relationship with his clients.
• Lean into Local: He learned that the most successful small breweries were scaling back national ambitions to focus on local distribution, leveraging their community ties and brand recognition.²⁷ This was the final piece of the puzzle. He had to stop fighting for every anonymous street hail across the five boroughs and start building a dedicated, high-value client base right in his own backyard.

The common thread running through the survival stories of bookstores and breweries was a conscious, deliberate strategy to de-commodify their product. Both Amazon and Uber had succeeded by turning their respective offerings—books and rides—into commodities, competing almost exclusively on price and convenience. The survivors, however, had escaped this race to the bottom by adding layers of value that a scaled, algorithm-driven competitor simply could not replicate. They offered expertise, trust, community, and a unique experience. The taxi industry, by competing for the same anonymous “point A to point B” trips, had allowed itself to be commodified. Michael’s epiphany was that the only viable path forward was to pivot to a model where his service was no longer a commodity. This meant targeting niche markets where reliability, trust, and professionalism were valued more than pure cost savings.

The following table synthesizes this cross-industry analysis into an actionable framework, demonstrating that a proven path to surviving disruption exists.

Table 3: The Adaptation Playbook: A Cross-Industry Guide to Surviving Disruption

Core Principle	Independent Bookstore Strategy	Craft Brewery Strategy	New Taxi Company Tactic
1. De-Commodify via Curation/Quality	Personalized “handselling” by expert staff; curating unique, niche book selections.	Focusing on unique, high-quality brews and innovative flavors, not mass production.	Focusing on professional, vetted drivers and premium, clean vehicles; ensuring impeccable service quality.
2. Build Community & Local Trust	Promoting “shop local” movements; becoming a hub for local culture and identity.	Emphasizing local identity; collaborating with local businesses and events.	Leveraging the driver’s deep local knowledge; building a reputation for reliability and safety within the community.
3. Create a Premium Experience/Destination	Creating inviting “third places”; hosting events like author talks and book clubs.	Designing experience-driven “tasting rooms” with live music, food, and events.	Offering premium services (e.g., airport meet-and-greet, corporate transport) that prioritize comfort and professionalism.
4. Leverage Technology for Niche Service	Using platforms like Bookshop.org to create an online presence that supports, not replaces, the physical store.	Using software to manage batch quality and costs for specialized brews.	Adopting apps for streamlined booking, billing, and communication for dedicated corporate or medical clients, not for mass-market hailing.

Source: Analysis based on.²³

Part 5: The Road Ahead: Building the New American Cab Company

Armed with his epiphany, Michael began the painstaking work of rebuilding his business from the ground up. The first step was a radical strategic shift. He stopped chasing the mass market. The endless, draining competition for the anonymous street hail was over. He was no longer a generalist; he would become a specialist.

The Pivot to Niche

Michael identified three high-value, underserved niches where his core strengths—reliability, professionalism, and deep local knowledge—were competitive advantages, not relics of a bygone era.

• Corporate Accounts: He started by creating professional marketing materials and directly contacting local businesses. He offered what rideshare platforms, with their fluctuating prices and variable driver quality, could not guarantee: a bespoke service for corporate clients. This included priority booking for important clients and visiting executives, the convenience of a single monthly invoice to streamline expense management, and the peace of mind that comes from using a vetted, professional, and reliable service.²⁸
• Non-Emergency Medical Transport (NEMT): Michael discovered a vast, government-supported market for transporting patients to and from medical appointments. He began the process of becoming a provider for Medicaid transportation, working with brokers like New York’s Medical Answering Services (MAS).³¹ This market valued punctuality and safety above all else. It offered consistent, pre-scheduled work and served a vulnerable population that needed the trust and assistance a professional driver could provide, a world away from the unpredictability of the gig economy.³²
• Luxury & Pre-Booked Services: Finally, he leaned into the high end of the market. He positioned his service as a premium alternative for airport transfers, special events, and “as-directed” hourly bookings. He couldn’t match the global fleet of a service like Carey, but he could compete on a personal touch and his unparalleled knowledge of the city’s rhythms.³⁴ For a tourist wanting a reliable airport pickup or a family needing a car for a wedding, his service offered a level of personalized care that larger, more impersonal services struggled to match.³⁶

Technology as a Tool, Not a Tyrant

Michael knew he couldn’t ignore technology. He invested in a modern booking and dispatch system, but his goal was different from Uber’s. He wasn’t building a platform to manage a fleet of thousands; he was using technology to provide a seamless, premium experience for a smaller, more valuable client base.³⁷ His new app allowed corporate travel managers to easily book and track rides for employees. It provided his NEMT partners with real-time updates. It allowed his private clients to pre-book airport runs and even request him specifically as their driver. Technology became a tool to enhance trust and efficiency, not a means of commodifying his labor.

Rebuilding the Brand

The final step was to rebuild his identity. The yellow cab was still an icon, but his brand was now something more: a professional ground transportation service. His value proposition was no longer just a ride, but a guarantee of safety, reliability, and the irreplaceable expertise of a veteran New York driver. He was, in a sense, returning to the ideal his grandfather Leo had embodied: the driver as a trusted “oracle on wheels,” now repackaged for the 21st century with a smartphone and a corporate account portal.

The road ahead for Michael, and for the American cab company, is not a return to the gilded age of the medallion monopoly. His victory is not a triumph over Uber, but a quieter, more profound success. By refusing to compete in a race to the bottom, he has found a sustainable path forward. His finances have stabilized, and he is methodically paying down his restructured medallion loan. He has found a way to survive, and even thrive, not by clinging to the past, but by identifying its most valuable qualities and skillfully bringing them into the future.

The ultimate evolution of this model points toward a new kind of fleet. The lone owner-operator, shattered by the medallion crisis, lacks the scale for marketing and technology. The massive TNC platform, built on a transient workforce, struggles to provide the consistent, high-trust service required by corporate and medical clients. The most resilient future likely lies in a hybrid: smaller, tech-enabled, professionally managed fleets focused on these high-value niches. These new fleets can combine the rigorous standards and professionalism of the old taxi model with the efficiency of modern technology. This would represent the true rebirth of the American cab company—not as a single, monolithic entity, but as a network of specialized, high-quality service providers who have learned the hard lesson that in the age of the algorithm, the most valuable commodity is trust.

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