1974: A Man Between Two Worlds

Buddy Jacobson’s transition from champion horse trainer to Manhattan real-estate operator

By 1974, Howard “Buddy” Jacobson was living between the world that had made him famous and the new life he was constructing in Manhattan.

Only a decade earlier, Buddy had been one of the most successful horse trainers in America. From 1963 through 1965, his horses won 509 races, and he captured five New York training titles. His aggressive claiming strategy, relentless work habits and willingness to challenge racing’s establishment had made him wealthy, feared and controversial.

But the relationship between Buddy and New York racing had deteriorated sharply.

The Fight with New York Racing

After organizing horsemen and backstretch workers during the 1969 Aqueduct labor dispute, Buddy became increasingly unpopular with powerful racing officials. A subsequent 45-day suspension was followed by the New York Racing Association’s refusal to provide him with stall space. Without stalls at Aqueduct, Belmont Park or Saratoga, a licensed trainer could possess horses but had little practical opportunity to compete in New York.

The conflict eventually became Howard Jacobson v. New York Racing Association.

On June 25, 1974, a Nassau County jury ruled in favor of NYRA in Buddy’s lawsuit over its refusal to allot him stalls. Buddy maintained that the racing association had acted maliciously, punishing him for criticizing its leadership and for his involvement with the Horsemen’s Benevolent and Protective Association. NYRA argued that its decision represented reasonable business judgment. The verdict went against Buddy, although the litigation would continue into the following year.

The case represented more than a disagreement over barn space. Racing had been Buddy’s world since childhood. He had entered the barns at approximately eleven years old under his uncle Eugene Jacobs and later followed the legendary Jacobs family into the upper ranks of the sport. His uncle Hirsch Jacobs had become a Hall of Fame trainer, while Buddy developed his own reputation as a master of claiming horses and rapid-fire victories.

Now the gates were effectively closed.

For nearly five years after his suspension, Buddy was denied stall space at New York tracks. He sued NYRA for millions but lost the original jury trial. Although he would regain stall space in 1975, by then his ambitions had moved well beyond the backstretch.

The Changing Face of New York

New York itself was changing in 1974.

Aqueduct opened its unusually long racing season beneath winter skies and disappointing attendance. The grandstand still attracted devoted horseplayers, trainers, bookmakers and working-class racing families, but the sport’s older dominance was beginning to weaken. The glamour remained at Belmont and Saratoga, yet the racing business was becoming more regulated, political and difficult for an independent operator such as Buddy to control.

Across Manhattan, a different culture was emerging.

Fashion photography, modeling agencies, late-night restaurants and private parties were becoming part of a new social economy. Young models arrived in New York hoping to appear in magazines and advertising campaigns. Wealthy businessmen purchased Upper East Side properties and transformed ordinary apartment buildings into fashionable addresses. Disco had begun moving out of underground clubs and into the city’s broader nightlife, although Studio 54 would not open until 1977.

For Buddy, real estate offered something racing no longer could: independence.

A racetrack required licenses, stall assignments and approval from officials. An apartment building belonged to the person whose name appeared on the deed. Buddy could negotiate the purchase, arrange the financing, renovate the apartments, select the tenants and operate the property according to his own instincts.

He began assembling the Manhattan real-estate holdings that would eventually become central to the Buddy Jacobson story. Later records showed millions of dollars in property sales and additional acquisitions. One of those properties was the Upper East Side building at 155 East 83rd Street—the address that would eventually connect Buddy, Melanie Cain and John “Jack” Tupper.

Dawn Eve Comes to New York

The year 1974 also brought a significant personal connection to the developing modeling side of Buddy’s story. That year, Dawn Eve was scouted in Minneapolis by Buddy Jacobson and Melanie Cain and invited to move to New York City to accept a modeling job. After arriving in Manhattan, she resided in the models’ penthouse associated with Buddy and Melanie’s growing fashion enterprise.

Dawn’s move reflected the way aspiring models were frequently discovered far from New York and brought into the city through personal introductions, agency arrangements and promises of professional opportunity. For a young woman arriving from Minneapolis, the experience represented an immediate entrance into a glamorous but unfamiliar world of photographers, castings, fashion assignments, business negotiations and Upper East Side social life.

The models’ penthouse was more than a residence. It became a gathering place for young women pursuing careers in fashion and advertising, as well as for the photographers, agents, businessmen and personalities moving through Buddy and Melanie’s expanding circle. The apartment would become one of the distinctive settings connected to the larger Buddy Jacobson story.

The Horseman Becomes a Manhattan Operator

Buddy did not simply retire from racing and become a conventional landlord. He brought the racetrack with him.

The same instincts that had allowed him to identify an undervalued claiming horse could be applied to a neglected building. The same appetite for leverage that allowed him to campaign a large stable could be used to finance property acquisitions. He was comfortable with risk, accustomed to operating on borrowed money and confident that he could recognize value before anyone else.

Years later, Buddy acknowledged that there was rarely a great deal of available cash behind his growing collection of properties. He was frequently mortgaged heavily, using one acquisition to support another. It was an ambitious system capable of producing rapid wealth, but it depended upon constant movement and continued access to financing.

His Manhattan buildings also placed Buddy near an entirely different cast of characters. Models, photographers, restaurant owners, attorneys, contractors, aspiring performers and nightlife personalities began replacing trainers, jockeys, grooms and horse owners in his daily life.

The transition would eventually lead to My Fair Lady, the modeling agency Buddy developed with Melanie Cain. Cain was a successful young model who had arrived in New York from Illinois and would become Buddy’s romantic and business partner. By the late 1970s, they were living together on East 83rd Street, surrounded by the properties, personalities and tensions that would later dominate the headlines.

A Cadillac in the City

The automobiles of 1974 reflected the size and confidence of the era. Long Cadillac Eldorados, Lincoln Continentals and Mercedes-Benz sedans moved through Manhattan streets lined with restaurants, doormen, taxis and brownstones.

A large Cadillac suited Buddy.

It communicated success without subtlety. It was part luxury automobile, part business office and part personal stage. Buddy could travel between Queens racetracks, Nassau County courtrooms, Upper East Side properties and late-night Manhattan meetings without ever appearing disconnected from the life he was building.

The Cadillac would later become one of the most recognizable objects in the Jacobson case. But in 1974, it represented something different: mobility, ambition and the belief that Buddy could leave one world behind and dominate another.

The Calm Before the Story Changed

Nothing that happened in 1974 made the later tragedy inevitable.

Buddy was a controversial horseman fighting a powerful racing organization. He was also becoming a real-estate investor during a turbulent period in New York history. His developing modeling business, his relationship with Melanie Cain and the expanding circle of young models around them were introducing new people and new ambitions into his life. The hospital conversion and the arrival of Jack Tupper remained in the future.

Nevertheless, the essential pieces were beginning to move into position.

The racetrack was fading from Buddy’s daily life. Manhattan property was replacing it. Young models were entering his social circle. His business interests were becoming more complicated, his financing more aggressive and his world increasingly removed from the structured rhythms of the racing calendar.

In 1974, Buddy Jacobson had not yet become the central figure in one of New York’s most sensational murder cases.

He was still the horse trainer who believed he had been unfairly driven from the sport.

He was still the Brooklyn outsider determined to beat the establishment.

And he was becoming the Upper East Side operator whose buildings, relationships and ambitions would soon place him at the center of a story that New York would never forget.