The Race Underground: Boston, New York, and the Incredible Rivalry That Built America's First Subway

by Most, Doug

  It was Whitney’s good fortune that in the second half of the nineteenth century Brookline, Massachusetts, was the perfect place to be dreaming big dreams. In 1871, the street railways of Boston carried 34 million passengers. Ten years later, that number would double to 68 million. There was nowhere else to build tracks unless the boundaries of Boston expanded, which put anybody who owned significant chunks of land on the outskirts of Boston in a most enviable position. In the wealthy enclave of Brookline, only a few miles from the congested downtown business district, Henry Whitney was the biggest landowner of them all.

  In the fall of 1878, Henry finally took another big step. His parents lived on Pleasant Street in Brookline, and one of their neighbors was the retired U.S. navy admiral Joseph F. Green. In 1878, Green’s youngest daughter, Margaret Green, was twenty years old. She was bright and beautiful and, to James Whitney’s oldest son, irresistible. She had short and curly brown hair pulled back from her pretty face. Though she had little formal education and came from a modest household, Margaret was bright and opinionated. She had never lived anywhere but Brookline. Henry, on the other hand, was wealthy, thanks to a portfolio full of shipping-company stock, and ambitious. And he had traveled all over the country. They were a handsome, if oddly matched, couple, but they fell in love after dating only a few months, and despite his being almost twice her age, on October 3, they married.

  Whitney and his bride settled into a red brick, ivy-covered mansion on Warren Street in Brookline’s Coolidge Corner very close to where his parents lived. For him, it was a natural transition into a large, meticulously maintained home like the ones he was raised in. But for Margaret, it was a bigger adjustment. She decorated the home with the assistance of designing experts and an almost unlimited budget. Leather-bound copies of all the classics, along with encyclopedias, were chosen to stock the library in the house. A Steinway grand piano was brought in, and beautiful oriental rugs were placed in every room. The walls were covered with artwork, etchings by Whistler, watercolors by Winslow Homer. Giant plaster replicas of the marble Parthenon frieze lined the winding staircase. The house was warm and inviting and appropriately New England, with heirlooms at every turn and a fireplace crackling. The home was cavernous for two people, and only the sound of children would change that.

  WILLIAM

  William C. Whitney was thirty-four years old when, in 1875, he took over the office of corporation counsel to the city of New York, at an impressive salary of $15,000 a year. The job was vital to the city. Whitney replaced a Tweed crony who had ignored the crime ring and thus made it even stronger and more difficult to take down. Not only did Whitney immediately fire anyone in his office with the slimmest connections to Tweed or Tammany Hall, but he replaced them with some of the most distinguished, well-respected, and brilliant lawyers in the city, men who would go on to be Supreme Court justices and U.S. circuit court judges. Their task was clear: clean up nearly four thousand pending suits against the city that were seeking in excess of $20 million, most of them from contractors hired by the Tweed ring that was now being dismantled piece by piece.

  In two years, Whitney reorganized the department and saved the city millions by exposing hundreds of frauds. More important, the job immersed him in city, state, and even national politics and helped him forge relationships with powerful men, like Governor Tilden, and a little-known mayor from Buffalo named Grover Cleveland.

  As corporation counsel, Whitney gained some unique insight into the operations of the city’s transportation systems. He took a particular interest in the two dozen or so independent street railway franchises clogging New York’s streets. The cars were filthy and uncomfortable, and the railways were constantly breaking down. Their owners paid virtually nothing to the city, and yet they had licenses that seemingly allowed them to go wherever they wanted, whenever they wanted, for as long as they were in business, with little regard for what was best for the city or for passengers. The railway companies cared only about how many fares they collected each day. And because crossing through the city often required the use of two or three different lines, if someone wanted to step off one car and transfer to another, well, that was more money in the pockets of the railway magnates. A free transfer was unheard of. Just as Alfred Beach almost three decades earlier, New York’s young and ambitious corporation counsel saw how these railway franchises held the people of New York hostage. In the horrendous clutter of New York’s streets, Whitney, too, perceived that there was a vast fortune just waiting to be made, if the right solution could be found.

  HENRY

  Henry Whitney’s marriage, followed by the sudden death of his father just three weeks later, made him a better man. Three children born in three years starting in 1879—Ruth, Elinor, and Laura—also helped him. Their last two children, James and Josephine, would come later. Henry accepted his new responsibilities and displayed an energy and focus that those close to him had never seen before. A close observer of Henry Whitney’s said that in managing his company’s affairs, “he exhibited for the first time, in a broad and striking manner, indomitable energy and resource.” In only a few years, between the steamship business and the water company that he also inherited, he rose to be the successful businessman his father had always hoped he’d become. His personal wealth soon approached half a million dollars, double what it had been around the time of his father’s death.

  The Massachusetts Board of Railroad Commissioners was supposed to bring order to Boston’s streets, but it granted charters to more than twenty companies to pick up passengers in downtown Boston. Instead of cheaper fares, organized routes, and controlled congestion, Boston had no fare system at all (fares ranged from five to ten cents), and there were overlapping routes in some areas, while others got no streetcar service at all. The competition created mayhem. Fast, slow, race, brake, the streetcars showed no regard for the passengers on board or those waiting to be picked up. “The car that was left behind would then fall back and go as slowly as possible in order to get passengers from the car in the rear,” one president of a rail company said. “All this led to blockades, accidents, and other serious injury to the service.” The more Whitney rode these lines, the more he believed he could fix them.

  Whitney was not yet in the streetcar business, but he was in the development business. And he was beginning to realize how much the two were intertwined. Without a fast and reliable transit system, there could be very little development. With each new piece of land in Brookline he bought up, Whitney’s prominence grew and it became obvious to observers that he had great intentions for all of that property. He was on his way toward investing more than $800,000, and he would soon own almost four million square feet of land in Brookline and neighboring Brighton, most of it along the main thoroughfare, Beacon Street. He also had his eyes on more properties that would give him another million square feet. He was lining up some of his closest friends, including Eben D. Jordan, a Maine merchant and the founder of a giant department store in Boston, and W. W. Clapp, the editor of a local newspaper, and together they set out to change the way the people of Boston moved through downtown and out to the growing suburbs.

  Whitney knew that Brookline was closer to the business district than many of the other communities Boston had swallowed. He traveled into Boston most days in a private carriage, a trip that took about an hour. Whitney took an easy route east from Coolidge Corner, down Beacon Street, through Kenmore Square, and right into the business district. For most of the way, the street was more than fifty feet wide, a straight thoroughfare unlike most of the narrow, twisting streets of Boston. And its width allowed a steady stream of horses to travel back and forth between Brookline and Boston without getting jammed up too tightly.

  On August 9, 1886, a petition signed by a hundred residents of Brookline was presented to the town selectmen. They wanted Brookline to take control of Beacon Street and convert it to what was called a townway. The selectmen approved it, and the land along Beacon Street immediately became m
ore valuable for anybody who owned there, putting Henry Whitney in an enviable position. One of the first things Brookline did was hire the same architect who had designed a necklace of connecting Boston parks a decade earlier. They asked Frederick Law Olmsted to landscape the wide boulevard of Beacon Street into Boston and make it into one of the prettiest streets in all of the country. As a Brookline park commissioner, Whitney knew Olmsted’s work. In hiring him for his own plan, he described Olmsted as “a man who stands second to none in this land for laying out avenues of this kind, whose fame extends from Maine to Mexico.” Whitney’s vision was to see Beacon Street, now dotted by only a few scattered mansions, become a busy thoroughfare not only lined with apartments, homes, and stores but also formed of two roads, not one. One would handle the personal vehicles of the wealthy residents. The other would be strictly for commercial vehicles coming in and out of Coolidge Corner. The boulevard would be two hundred feet wide, flanked on both sides by bicycle and bridle paths, and lined in the middle by American elm trees.

  But that wasn’t all. The signature piece of his plan was in between the rows of elms. There, Whitney wanted a street railway track, slightly hidden by the trees so that the cars would feel less intrusive to the community. Whitney knew that in 1884, one of Boston’s biggest streetcar companies, Metropolitan Railroad, had tried to build a streetcar line from Brookline to Boston, but was denied by the state legislature.

  Three years later, he was determined to avoid the same fate. At a hearing in January 1887 before Brookline’s Committee on Roads and Bridges, Whitney admitted that, yes, his plan, if successful, would most likely bring him great riches. But he pointed out that others would benefit, too, and that proved key to convincing other landowners along Beacon Street to give their land to the project. The only objectors to his scheme feared higher taxes and argued that the widening would benefit the richest the most. These were points nobody could argue with, but there was not enough opposition, and shortly after Brookline’s committee approved Whitney’s plan, the state legislature did as well.

  Whitney next set out to create a subsidiary of his land company, called the West End Street Railway Company, to build and manage a street railroad along the beautiful new boulevard and connect Boston’s downtown with the blossoming and affluent suburb of Brookline. And he made an offer Brookline could not refuse. He gave the town 630,000 square feet of his own land, which was just over 10 percent of his total land holdings. But it was almost half the total needed to complete the widening of Beacon Street. And he also agreed to donate $100,000 to the project if Brookline gave the remainder, which put his share of the total cost around one-third. Both of these offers were generous and shrewd. Travel by rail was quickly becoming popular in America. In 1880, the country’s railroads and street railways had carried 59 million people. By 1885, the figure was up to 80 million. And by 1887, it was more than 90 million and climbing.

  By convincing the town to widen the boulevard and build approximately eight miles of suburban tracks, Henry Whitney guaranteed that his remaining properties would skyrocket in value. And with his actions, real estate was no longer his biggest enterprise. Henry Whitney was now in the transit business. His brother would soon join him.

  WILLIAM

  In 1878, after very little debate, New York City had opened its first elevated, steam-powered train line, the Sixth Avenue elevated, and soon Els were running along Second, Third, and Ninth avenues. The city was no longer bursting at its Forty-second Street seams, and with the Els came rapid development into the Fifties, Sixties, Seventies, and even as high as Eighty-third Street. New York had the first legitimate rapid transit system of any kind in the country and the first network of elevated railway lines in the world. It was from this growth that New York’s newest fashionable neighborhood emerged, Fifth Avenue, through the East Fifties.

  William and Flora Whitney had been content in their home at 74 Park Avenue near Fortieth Street. They had lived there since marrying and had seen three children born there. Only a few months after James Whitney’s death, they were not particularly in the mood to uproot. But when Oliver Payne, Flora’s brother and William’s classmate from Yale, learned that one of the city’s most historic homes, the red brick Frederick W. Stevens mansion at 2 West Fifty-seventh Street at the corner of Fifth Avenue, was for sale at a price between $600,000 and $700,000, he had to buy it for his sister. Oliver was a bachelor, and as the one who introduced them, he had taken it upon himself to play sort of a paternal figure for the couple.

  It filled four city lots and was blocked at the front by iron-grille doors. The winding central staircase carved out of dark wood was spectacular, and the library on the ground floor covered almost half the length of the home. As beautiful as it was, the Whitneys had to go shopping to fill it, and Flora did so with great enthusiasm. She covered the floors with rich oriental rugs and the walls with bright tapestries and works by the French painter François Boucher, whom Whitney had a special affection for. The Whitneys may have left behind the neighborhood of the Morgans, but in their new home, they were trading up to live across the street from Cornelius Vanderbilt II, whose daughter Gertrude would in a few years marry Will Whitney’s oldest son, Harry. It was that marriage that assured the Whitney family’s legacy would thrive into the twentieth century and beyond. Gertrude Vanderbilt Whitney became a prominent sculptor and art collector, and after she established the Whitney Studio in Greenwich Village in 1914 and accumulated more than five hundred works of art, she offered them with an endowment to the Metropolitan Museum of Art. When the Met rejected her, she founded her own museum, the Whitney Museum of American Art, on West Eighth Street, for young artists. It would become one of the great enduring legacies of the Whitney family.

  Whitney’s four-year term as New York City’s corporation counsel ended in 1880, and he briefly considered leaving and returning to private practice. But he accepted a second term, and he began to weigh his next move. As for Flora, she threw herself into entertaining. It was a role she relished—and that her husband despised. But Whitney was nothing if not savvy. He recognized that his wife could help him make his own fortune and chart his own course. And so Flora Payne Whitney became New York’s grande dame of elegant dinner parties. And William Collins Whitney, already an important man in New York who had horses, yachts, museum-worthy paintings, and an entire library of books at his disposal, set his sights on leaving the law and turning to politics.

  * * *

  ON A FEBRUARY MORNING in 1882, William Whitney was driving his carriage through the north stretch of Central Park. Riding his horses provided him with a rare moment of solitude away from his four children, the dizzying social calendar that his wife kept for them, and his tedious legal work. He enjoyed riding despite how harried the streets could be at certain hours. Only the wealthiest New York residents had private carriages, and because Whitney’s parents, both skilled riders, had taught him well as a boy, he insisted on driving his own horses whenever he could.

  On this winter day, the forty-one-year-old Whitney was ready to head for home when he pulled up behind a pair of chestnuts trotting through the park more slowly than he preferred. Impatient, he steered his animals out of the park onto Fifth Avenue heading south and pushed them to pick up the pace. He had gone only two blocks when he saw a large wagon heading in his direction. Just as they neared, a handcart pushed by a boy veered out from behind the wagon. Whitney’s horses dashed across the avenue, still in his control, until they came upon another wagon. He tried desperately to straighten them out, but instead he lost the reins. In an instant, Whitney was flying through the air. His carriage had struck a curb and tossed him clear into a telegraph pole, while his horses ran ahead without him down to Eighty-third Street. One of them broke a leg and caused the other to stop. The injured horse was shot dead on the street by a police officer, while a battered Whitney was taken home. His doctors were called to his mansion, and they told him that while he was a lucky man, he had fractured his left ankle, bruised his
left knee, and sprained his left wrist. Bed rest, they ordered. Whitney had hoped that a leisurely ride might clear his head so he could think about the next chapter in his career. Instead, it had landed him on crutches. Telling him to sit still proved fruitless, since only a few days later, still bandaged in splints, he got himself back into his carriage for another ride. But that only set his recovery back further, while providing endless amusement for the city’s papers like The Tribune. “Tammany may as well take warning,” the paper wrote. “There’s no use trying to upset or break down this man. He doesn’t know when he’s smashed up and keeps right on as usual!”

  That was certainly true. But after a decade bogged down in the minutiae of city politics, Whitney was ready for his next challenge. He had no idea how much his life was about to change.

  * * *

  ON MONDAY, NOVEMBER 6, 1882, eight months after his riding accident, Whitney sent his letter of resignation to New York’s newest mayor, Democrat William R. Grace.

  Whitney chose the day before the election to step down because he had put hundreds of hours into backing the campaign of the Democratic candidate for governor and wanted to enjoy the election without worrying about any implications on his job. He also wanted to return to private practice. He had collected a wealth of expertise in finance, taxation, and franchises, and along with his past experience in banking, real estate, and transportation, he hoped to build a thriving practice and finally make his own fortune. His resignation letter summarized what he had told a reporter a few weeks earlier, when he said, “I am exceedingly anxious to get out of the office.” Unanimously, the newspapers praised his seven years of service as corporation counsel, and some predicted that the Democratic party would be wise to find a powerful place for him.

  Even if he had no interest in running for elected office again, after a disastrous run for district attorney early in his career, Whitney still loved the game of politics. When Buffalo’s mayor, Grover Cleveland, considered a run for governor early in 1882 and sent an aide down to the city to collect the advice of a few trusted and respected political leaders, Whitney was blunt with the aide. Go back upstate, he said. Build a stable of delegates who will support Cleveland no matter what, and then we’ll talk. Privately, Whitney was sure Cleveland had no chance, even though he did like and respect him for the way he ignored anyone with ties to the Tammany Hall machine.