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

by Most, Doug

  WILLIAM

  Henry was not exceptionally close with his younger brother, William Collins Whitney, while growing up, even though they were only two years apart. But over the course of the second half of the nineteenth century, as they traded occasional letters; mourned the losses of parents, siblings, and even children; married and raised their own families; loaned each other money; and rose up to become powerful businessmen in New York and Boston, no two siblings would change the course of life in the American city more than the Whitney brothers. They did not compete with each other so much as they observed and learned from each other. But it wasn’t always that way. Only one of them, it could be said, was driven to succeed from his youngest days.

  Where studies were of little interest to Henry, William was called Deacon for his habit of reading the Bible for hours beneath the shady trees by the river near their home. In 1856, the two boys attended Williston Seminary, a new boarding school in nearby Easthampton. Their school was chosen for good reason, especially given that its tuition, nine dollars a year, was not inexpensive for the times. It was founded by a long-ago uncle of the boys.

  At Williston Academy, nobody was allowed to coast, which is perhaps why only one of the Whitney brothers managed to sustain the grades and level of interest the private school demanded of its students. Will was the serious one who studied Homer and Virgil, algebra, and geography. He focused especially hard on the headmaster’s Bible study course. After graduating Williston, Will Whitney wanted to attend West Point and to follow the path of his father by joining the military. With his education and James Whitney’s connections, gaining acceptance to the academy would not have been a problem. The problem was that his father did not want that for his son. The idea of Will in the army depressed his father so much that Laurinda finally had to go visit Will and make him an alternative proposal. She begged him to choose Harvard, Yale, or Williams, and he relented, enrolling in 1859 at Yale, where the tuition of $216, while unaffordable to most families, was well within reason for the comfortable Whitneys. Will excelled in one area that fascinated him. Debate. He also made some of his best and lifelong friends, including a rich and equally ambitious young man from Cleveland, Ohio, named Oliver Hazard Payne, an economist named William Graham Sumner, and Henry Dimock, who would join Will Whitney not only in a Wall Street law practice but also in family, when he married Whitney’s sister Susan. While some of Whitney’s classmates left school in 1861 to join the fight as the Civil War began, he did not. Instead, Whitney enjoyed his time at Yale, rowing on the crew team, joining Skull and Bones, and excelling in English composition. The law in particular called to him, and as graduation neared and he was presented the opportunity to make a commencement speech, he seized the moment.

  On July 30, 1863, speaking to his graduation class and with the esteemed Yale faculty members seated behind him, he railed against Republicans, against the Civil War, and against immigration, and he took particular umbrage at what he perceived as a shortage of bright and ambitious men seeking public office. As with every previous Yale address, Whitney, wearing a slim-fitting suit and high waistcoat, spoke from memory, at least at the start. The expectation of the school’s elders was that the student should be so honored to speak that they would stand in front of a mirror for hours rehearsing their speech until it was just so. “The Drama closes when the nation, sick at heart and worn out by faction and misrule, sinks out of sight in history, or yields itself a willing victim to some ambitious and able usurper,” Whitney said. His classmates gasped at his words, but there was greater shock when he paused, reached into his pocket, and calmly pulled out the rest of his speech and continued to read it, thinking nothing of the sacred tradition he was breaking.

  Afterward, when his good friend Sumner asked him why he did not follow the rule of reciting his speech by memory, Whitney seemed nonchalant about his brazen act. “It was too much bother to memorize so many words,” he answered.

  He moved back home after Yale so that he could attend Harvard Law School with his friend Henry Dimock. But Will’s patience with schooling was fading. Though Harvard Law School at the time claimed some of the great legal minds in the country, they could not hold the attention of the two chummy Yalies. Barely one year after enrolling, Whitney and Dimock left Harvard, convinced they could just as easily pass the bar requirements and become lawyers by clerking in a law office as they could by sitting in a boring classroom on the Charles River. And they were not interested in clerking in Boston. Nowhere was the legal field more cutthroat than in New York, and competitor that he was, Will Whitney was drawn to it. He arrived in Manhattan in the fall of 1864 with grand ambitions, and the streets and social scene of Gotham would never be the same.

  HENRY

  By the time he was well into his thirties, Henry Whitney had collected a range of business experiences, most of them in banking and shipping, running the Metropolitan Steamship Company his father had launched. But he had no career to speak of or family to surround himself with. After leaving Williston early, Henry had never attempted college. Any real jobs he’d held he owed to his father, not to his own hard work or entrepreneurial spirit. He worked in his father’s store, he clerked in his father’s bank. As he was approaching forty years old, Henry had even followed his parents and moved into a house right near them in Brookline, a large home on Pleasant Street in the neighborhood known as Coolidge Corner. The only reason he was financially sound was because his father’s businesses had done well. Henry owned more than half the shares of the Metropolitan Steamship Company. But even Henry knew that he was still lost, and it bothered him.

  “My dear Bill,” Henry wrote in a letter on May 10, 1865, while in Alabama. “I have but a moment in which to write and will therefore be brief. The weather is now oppressingly warm and I have thus far enjoyed the trip.” His letter told of a man who ran a cotton mill and who was quite the inventor, but needed help securing a patent. “I have told him that you would probably call,” Henry said. A month later, Henry wrote to his brother again, this time to say he was considering leaving the north for good and settling down south. “If there was anything in New York that I might turn my hand to,” he wrote, “that would suffice to procure me daily bread, and some of the entrées and dessert, I would not think of leaving at all. And it must be that there is plenty to do if one is only willing, patient and persevering.”

  Henry was neither willing nor patient nor persevering. But he couldn’t change. Life had become one adventure after another, and as he bounced from Mobile, Alabama, to Pensacola, Florida, to New Orleans, his name was a commodity only because of his bloodline.

  “His own means don’t amount to much,” one newspaper story said of Henry. “Operates in connection with his father and not supposed to have much personal responsibility.”

  It was a perception he was determined to change. The second half of the nineteenth century was an exhilarating time to be a dreamer in Boston. The city was a magnet for men with great personal ambitions but no stable business to speak of. Henry Whitney would fit right in. But not everyone found comfort so easily in Boston.

  In March 1868, a scraggly dressed drifter from Ohio with nothing in his pockets arrived in the city looking for a job. It didn’t take him long to find work at a local Western Union branch. His coworkers were more educated than he; most of them were college graduates, while he had not even finished high school. But none of them were as curious or as well read or as skilled in telegraphy as their newest colleague, Thomas Edison.

  Edison befriended an inventor whose small shop at 109 Court Street in Boston’s Scollay Square had for twenty years been a place where an assortment of bells, batteries, alarms, and other gadgets had been born. The walls were covered in soot and dirt, and the ceiling beams overhead were caked in dust. Not an inch of floor space was left unused. There were pulleys whirring, leather belts racing, racks of steel and castings scattered about the floor. A loud steam engine helped keep the place warm. Edison was at home working here, and it was
n’t long before he got a patent for his first invention, an automatic vote-counting machine, and he proudly took it down to Washington to show the politicians there how much easier voting could be. In the nation’s capital, Edison got a lesson in politics. It turned out that politicians didn’t want it to be easier to cast a vote. They liked their traditional way of shouting out yay or nay because it provided a way to stall a bill if they were opposed to it. If they said nothing, nothing happened. But a voting machine would make stalling impossible, and they sent Edison back to Boston.

  After a few more months on Court Street, and a few more promising inventions that went nowhere, including a stock ticker, Edison decided he was not going to be able to achieve what he wanted in Boston. Still broke, he left his equipment and headed south in 1869, just one year after arriving. Edison’s year in Boston may not have been his most fruitful, but it sparked in him the desire to do something special. His time would come. When it did, Henry Whitney would be there.

  WILLIAM

  The heart of New York in the late 1860s was lower Manhattan, and there was very little development north of Thirty-fourth Street. Broadway, Fifth Avenue, and Park Avenue were all swarmed with horse-pulled coaches and wagons, to the point where it became a parlor game to see how many vehicles would pass by a single spot in an hour, morning, or full day. One curious businessman stood at the corner of Broadway and Chambers Street for thirteen hours one day in 1852 and counted an average of 470 vehicles passing by in both directions every hour. The gap between one car and the next was usually thirteen seconds. Fifteen years later, in 1867, a reporter for The New York Tribune, wondering how much things had changed, conducted the same experiment for the same period of time. In thirteen hours, he counted 13,391 vehicles in total, or 1,030 every hour, the absurd equivalent of 17 every minute.

  The conditions were perfect for entrepreneurs like Alfred Beach to develop solutions. But as Beach learned, and as Will Whitney would soon discover, dirty politics in New York always won out over the public’s clamor for improved services.

  As his law practice with Dimock grew, Whitney saw that culture was one way to establish his place in the city. He learned to love opera, gained membership to the Century Club, and found himself shoulder to shoulder with the city’s elite, from John Jay to Edwin Godkin to J. P. Morgan. And when the American Museum of Natural History opened, he took an immediate interest that helped him become a trustee there. As Whitney’s stature grew, he began to think about the state of his city and ways to make it more livable. You cannot ride in New York City, Mark Twain would write, “unless you are willing to go in a packed omnibus that labors and plunges and struggles along at the rate of three miles in four hours and a half.” As miserable as sitting was, standing was worse. “They are so crowded,” Twain wrote, “you will have to hang on by your eye-lashes and your toe-nails.”

  In 1867, sensing the power that Whitney might one day hold, a Michigan railroad man named Hugh B. Willson, who had witnessed the opening of the London subway four years earlier, mailed Whitney an outline for his own plans to build a similar project in New York. He had designed a subway tunnel to be constructed under Broadway and powered by steam. And he even suggested a brilliant idea to make it profitable: use the tracks for freight trains between midnight and six in the morning. Willson hoped to get a man like Whitney to purchase stock in his company and even act as its director, which would give it credibility. But Whitney wasn’t yet sold on London’s subway.

  “I am entirely satisfied that the time has come when some kind of steam railroad must be built on the island of New York in order to transport the passengers,” Whitney wrote to Willson. “If no other mode were practicable, I should advocate the construction of the underground railroad, not only as a necessity but as a paying investment. But the result of my observation in London leads me to prefer greatly the elevated railway, and believing it to be entirely feasible and not more expensive than the underground system, I cannot act as a Director in your company and do not wish to take any stock. In all my conclusions I may be mistaken, but I think it is better to state them frankly.”

  By 1867, with his practice stable and one of his biggest clients the Metropolitan Steamship Company run by his father and brother, Will Whitney had reconnected with his college friend Oliver Payne. Payne, unlike Whitney, had fought with the Union Army during the war and survived battle injuries, and when he returned home to Cleveland, his father, a wealthy businessman and popular Democratic congressman, handed him $20,000 and sent him out into the world to grow the family fortune in oil and iron. His first destination was New York, where about 1,500 families earned more than half of the city’s wealth. The few dozen millionaires who lived in the city at the start of the Civil War in 1860 now numbered several hundred, including some worth more than $20 million. That was the sort of company the Paynes were used to keeping, and in the winter of 1868 Oliver Payne paid a visit to New York and to Whitney. He came with a guest.

  * * *

  FLORA PAYNE WAS A hell-raiser. Six months younger than Will Whitney and the sister of his college roommate, she was not beautiful and had a square face and almost masculine jawline. But her outward confidence made her appealing to men who could match her self-assuredness. She had been properly schooled as a young lady, first in Cleveland and then in New York. But she hated etiquette lessons and often fled school and flaunted any punishment thrown her way. Her father hoped a more strict school in Cambridge, Massachusetts, might fix her, but her Midwestern blood was not a good match for the uptight, puritanical Boston bluebloods, and she couldn’t retreat home fast enough.

  During a visit to the Fifth Avenue Hotel to see her brother in February 1868, Flora was introduced to Will Whitney by Oliver. He suspected they might be a match. The handsome, slim, brainy, six-foot-tall lawyer and the brown-haired, graceful, well-traveled Midwestern daughter of a rich senator were smitten. Years later, Oliver would admit that he was sure if the two ever met “they would fall in love with each other.” So sure was he that he arranged for them to meet not just at the hotel, but in the romantic, top-floor dining room overlooking New York City.

  In a letter he wrote to Flora years later, Whitney described that first meeting and admitted to being flustered by her brashness. “How you looked I plainly recall in your blue dress and with the blue and gold book in your hand when you threw down the gauntlet for a flirtation. ‘So you are the Will Whitney that I have had held up to me for so many years?’ I must have been a little blundering at picking it up I imagine, for the attack was unexpected and bold … You asked me to order for you and then criticized and complimented until my time to go.”

  They went to dinner together, saw the opera, sipped tea late into the night, and flirted openly. And when she returned home to Cleveland, they began to fall in love through an almost daily flow of intimate letters back and forth, until finally she invited him out to meet her parents. He was prepared to propose to her on that trip, but, unsure of her willingness to commit, he hesitated. He almost scared her off, in fact, with a letter in which he wrote of having six young ladies that he loved with all his heart. “Henry and I won’t ever marry,” Whitney wrote. But it was merely his way to draw her closer, and on her next visit to New York, in December 1868, he decided the time was right. Flora got them tickets to the opera, and he arranged for a carriage, but she, in her typical sarcastic wit, wrote him a few days before to say the ride was unnecessary. “The carriage would undoubtedly be a vast ornament to us,” she wrote, “but as I am in good health I would suggest we walk the three steps that lie between the hotel and the Opera House.” Whitney was hooked. He adored the way she spoke her mind, and after he proposed and she accepted, they raced back to Cleveland to share the news and get her father’s approval. Of course he approved, and while Whitney returned to his job in New York, Flora stayed behind to start planning their wedding, and their life.

  They married at Cleveland’s First Presbyterian Church on October 13, 1869, and the groomsmen included Whitney
’s best friends, William Sumner and Oliver Payne, and his brother from Boston, Henry. They honeymooned in Niagara Falls before stopping in Canada and then Brookline to see Whitney’s family. It was the first time Flora had met Whitney’s mother, and Laurinda was quite impressed with her new daughter-in-law.

  “You have got a sweet, good wife, William,” she told him before they left, and she made him promise that he would love and respect her even when times got rough.

  Flora’s father gave the couple money to start their life in grand style, by building a brownstone in the fashionable Murray Hill neighborhood on Park Avenue. They had two servants and a cook. And within five years they also had three children, Harry, Pauline, and William Payne Whitney. A fourth, Olive, would come later.

  HENRY

  In October 1868, Henry’s impatience began to resurface. He had bought two parcels of land in Brookline, almost seventy thousand square feet, on a hunch that the land would be valuable one day. It paid off quicker than he could have imagined. Three and a half years after buying the tracts, in 1872, he sold the land for more than twice what he had paid. The deal marked the beginning of Henry’s transition ashore, from a maritime shipping magnate running the Metropolitan Steamship Company to a businessman who saw even greater potential in real estate and in the role that it could play in the growing world of street railways.