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  Dan had been born at the end of the torrid summer of 1819, during which mosquito infestations brought a yellow fever epidemic to the 125,000 inhabitants of New York, killing hundreds a day. At the time of the birth of the only child to George Garret Sickles and Susan Marsh Sickles, the city did not go much past Fourteenth Street. Beyond that point, cottages, immigrant shacks, farms, market gardens, and an occasional splendid country house were scattered northward in increasingly rustic locales. In town, few if any secular buildings rose more than five stories; church spires dominated the skylines, answered only by the worldly spires of the ships at anchor or docked in the Hudson and the East River. Yet within its narrow limits, the city already possessed an acute sense of its self-worth, a sense that Dan inherited.

  The factors that ensured the growth and splendor of young Dan’s town were already in place. A series of the first regularly scheduled packets, or steamers, were operating from the docks of Lower Manhattan. Until now, those who sent products from America to the mills of Europe had had to wait on the convenience of ships’ masters. But the regular departures of the Black Ball Line, already popular with the cotton planters of the South, would become even more popular with the expansion of north-south railroads. The connection with Southern interests meant that many of the business and political figures of New York, including Dan’s father, considered themselves honorary Southerners, and Democratic families like the Sickleses looked upon the Democrats of the South as allies and brothers.5

  George Sickles had passed on to his son a pride in being a congenital New Yorker, being a Knickerbocker—a descendant, through six generations, of the Van Sickelns, Dutch settlers of New Amsterdam. And, in the Knickerbocker tradition, George Sickles would always be a devout speculator in whom hardheadedness and impulsiveness were combined. He was, like his boy, an intensely charming man, verbally vivacious, canny, but ardent and even poetic. Dan found his mother, Susan Marsh Sickles, a gentler, more timid soul. She was generous but also neurotically pietistic, which made her adolescent son something of a stranger to her. She was a parishioner of Trinity Church, the oldest and most richly endowed church of Lower Manhattan.

  The young Dan, neat-boned and wiry, with blue eyes and brown hair, delighted his parents with cleverness but confused them with a turbulence that the father was better equipped to understand than the mother. Though always open to the force of reason or persuasion, “the moment the rod was raised,” as Harper’s Weekly said, “he became a rebel.” George Sickles sent his adolescent son upstate to tranquil Glens Falls. But reacting to a thrashing from the school’s preceptor, Dan walked out and took a job in the office of the Glens Falls Messenger. When his parents visited him at Glens Falls, they suggested that he study with a glamorous don whom George Sickles had recently met, Dr. Lorenzo Da Ponte, professor of philosophy and belles lettres at the recently founded New York University. Lorenzo, popular with young men of college age because of his combination of drollness and brilliance, would prepare Dan for entry into NYU. Dan responded to the professor with the total devotion he would always accord to male friends.

  George Sickles, then in the real estate market, purchased, in the second half of 1835, 2 Abingdon Square, off Hudson Street, and opened an office in Wall Street from which to trade and to administer his property. George accurately understood his son’s temperament, its power to attract faith and friendship from others, and its disordered hungers too. For that reason, he bought a beautiful farm across the Hudson, in Livingston, New Jersey, west of Newark. He had decided after all that Dan, though still young, did not have the academic grounding for NYU but might pursue agricultural science in Livingston, and become, perhaps, a scholar-agriculturist, like Thomas Jefferson.

  From the start, however, Dan did not make a good rustic, and agriculture and the seasons—whether as a study or as rural drudgery—did not answer the needs of his lively intellect or his urban nature. As a child, he had already developed a pattern of registering his unhappiness by means of more extreme gestures than most, and a journalist later wrote, “He manifested a resolution which amounted to sternness.” Early one morning he simply walked off the farm, went to Princeton, and took a job in a printing office. He thought of joining the navy when, in the last days of 1837, an American steamer, the Caroline, was set on fire by the Royal Navy and sent over the falls of Niagara wrapped in a shroud of flames. Raised on memories of the War of 1812, Dan was anxious to have at the British. Happily, his employer dissuaded him.

  Dan was much later accused of having at this time embezzled $100 belonging to a Mr. Peter Cooper, a venerable man who had taken a liking to him and had proposed to send him to Princeton University so that he could prepare to become a Presbyterian minister, another unlikely vocation for the young man. Cooper had apparently entrusted Dan with money to carry out a business transaction, and some went missing. We don’t know if the story is true, but accusations that he was at best inexact with money would follow him all his life.

  Moving on from Princeton, Dan walked to Philadelphia, arriving late at night, and knocked at the door of a fashionable boardinghouse near the Exchange. His manner and appearance so impressed one of the gentlemen boarders that he took Dan into his elegant suite of rooms, rent-free. Dan got work as a printer at Burton’s Magazine, a humorous weekly, but George Sickles had him located and wrote to him, pleading that he come home, since his mother was pining, and offering him every help with a liberal education. And so the boy returned to New York and to the comprehensive education offered by the Da Ponte household.6

  The senior Lorenzo, who took time to converse with Dan, had been born of Jewish parents in 1749 in Ceneda in northern Italy. The bishop of Ceneda converted Lorenzo’s parents to Catholicism and became a patron to the two bright sons of the marriage. Ordained a priest after an academically brilliant seminary career, Father Lorenzo Da Ponte embarked on a three-year affair with a young woman of Venice. She was not his only love. He liked to amuse listeners with such tales as how he had once been mistakenly invited aboard a gondola—he was not the man the girl aboard was expecting—and how this had led to such an intense amour that the woman in question had to be locked away in a convent by order of the Venetian Inquisitori di Stato. Lorenzo himself took a post in the seminary at Traviso as the professor of Italian literature, with a notable interest in erotic poetry. This time he was reported to the Reformatori, the Venetian Ministry of Culture and Theology, for his own erotic verse, and in 1776 was expelled from the seminary. He remained in Venice, however, and met a man who was not designed to improve his behavior, the libertine Giacomo Casanova, with whom he attended the theaters and still less salutary places. The fact that there were but two degrees of separation between Sickles, the young student of New York, and Casanova, the fabled prince of Priapus, did nothing to quell Dan’s adolescent sexual appetite.

  Da Ponte’s movements through Europe, the details of which he later relayed to fascinated students at Columbia and visitors to Spring Street, were often recoils from catastrophic affairs. His Venetian patron, Signor Memmo, expelled him from his house over a girl named Teresa, Memmo’s mistress. He went to Padua and was denounced again for public concubinage and adultery. Driven from Italy, he traveled to Vienna, to Dresden, and back to Vienna, earning his keep as poet and writer of melodramas, and achieving sufficient renown that in 1782, when Emperor Joseph II established an Italian theater in Vienna, he appointed Da Ponte as its poet, giving him the task of writing Italian melodramas to the music of Salieri. His first play was a complete fiasco, but his next, The Barber of Good Heart, was a grand success.

  Yet the story as Da Ponte told it to Dan had just begun. Da Ponte met Salieri’s young rival, Wolfgang Amadeus Mozart, in early 1783, and was given the job of translating Beaumarchais’s play Mariage de Figaro into a libretto for an opera, which was performed in Vienna three years later to stupendous acclaim. Da Ponte then began work on the libretto of Mozart’s Don Giovanni, performed the following year. Così fan Tutte was the third success for Mozart
and Da Ponte. But without warning, Da Ponte was asked to leave Vienna because of an offense to Emperor Joseph. His mistress, Nancy, a German girl he had met in Trieste, accompanied him to London, where he married her and worked as a writer for the Drury Lane Theatre. After nearly two decades of successful productions, and for unspecified reasons, he moved to New York in 1805. It was from Da Ponte’s stories of European intrigues and imperial artistic projects that Dan went forth to classes at NYU and to Democratic politics.

  At the age of ninety, on August 17, 1838, Da Ponte the elder died and was buried in an unmarked grave—a form of homage to Mozart— in the Catholic cemetery at Second Avenue near Eleventh Street. Maestro Bagioli now became the head of the household on Spring Street. Da Ponte’s son, Dan’s beloved mentor, Lorenzo the younger, was himself in bad health, suffering from a rare form of tuberculosis. In the winter months of early 1840, when Dan was a few years into his NYU studies, Lorenzo caught pneumonia and was himself buried before a crowd of mourners who included many students from the university.

  One of Dan’s fellow undergraduates, Charles Bulkley, was typical of the friends Dan attracted from the polite community. Bulkley noted how, as Da Ponte’s coffin was lowered, a spasm of grief racked Dan and he became hysterical. “He raved, and tore up and down the graveyard shrieking . . . so much so that it was impossible for us who were his friends to mollify him in any measure by words; we were obliged to take hold of him and by friendly force restrain him, and thus ultimately we took him out of the cemetery.” Meeting Dan a few days later, Bulkley found him displaying a lightheartedness that seemed unnatural “in contrast with the grief he had exhibited two days before.” Bulkley concluded that Dan was subject to sudden emotions and frenzied displays.7

  And now that scholarship incarnate had been laid beneath the soil, Dan decided that he was done with academia. After two years of residence in the Da Ponte household, he took rooms in a Broadway boardinghouse. He wanted to become a lawyer and, with his usual luck at making influential connections, began his studies for the bar at the offices of Benjamin F. Butler, a Democrat who had been the law partner of President Martin Van Buren, had served as U.S. Attorney General in Andrew Jackson’s administration, and had also briefly been Secretary of War. In placing Dan in Butler’s offices, two influences were at work: that of his wealthy Wall Street father, and that of the leaders of Tammany, who wished to groom the talented boy. For those with connections, admission to the New York bar could be, after the passage of enough time and the reading of a certain amount of case law, a formality, exempt from any intense or stringent examination.

  Dan’s energetic father, a man of confident robustness, decided to read law along with his son, and was, a year after Dan, admitted to the bar, with the proud boast that he was New York’s first patent lawyer. Around 1843, Dan opened law offices at 79 Nassau Street, near City Hall, in a building George Sickles had acquired. There they sat and discussed and studied together, the father memorizing case law from his son’s texts. George also made 79 Nassau his headquarters.8

  Dan was a frequent spokesman for Democratic Party principles, which already included a passionate belief in Manifest Destiny and the right of the United States to acquire and hold Texas, New Mexico, California, perhaps the isthmus of Central America, and certainly Cuba. They embraced a tolerance for immigration, based on the role of the Irish as a continuous stream of New York electoral fodder, every Irishman representing one vote (or, some cynics said, two or three votes) on election day. Democrats also wanted the government to drive a hard bargain with Britain regarding the Oregon-Canada border, and their war cry was “Fifty-four Forty [54 degrees 40 minutes latitude, that is] or Fight!” Another foundation stone of the New York Democrats was the intense commercial relationship between New York and the South, and thus the support, offered sometimes grudgingly but usually with a sort of neutral enthusiasm, of the South’s most notable institution: slavery.

  By 1844 Dan had written and issued an impressive campaign paper based on these principles, and promoting the election of the Democratic candidates for the presidency and vice presidency, James Polk and George Dallas. He also appeared in a patent case that year, representing two engineers who opposed the renewal of a patent for planing machines lodged by a competitor. One of the U.S. Patent Commissioners hearing the case was Daniel Webster, who gave special praise to young Dan Sickles’s advocacy on behalf of his two clients.9

  Dan still eschewed his parents’ home, perhaps because his father understood him too well and his mother’s attention cloyed. In 1844 his rooms were only a block and a half from 422 Broome Street, where the Bagiolis now lived, and he called there frequently. The child Teresa was eight years old, conversationally lively, smiling, and uncapricious. Dan was her beau ideal: he dressed superbly, liked to eat at Delmonico’s, was an aficionado of the theater. She did not comprehend, of course, that he attended brothels and never had enough money. Nor that he had been accused, rightly or wrongly, of raising $1,000 to produce a political pamphlet that never appeared, and of spending the money instead at a fashionable watering place, probably Saratoga Springs, whose great white hotels and sunny ambience he always loved.10

  And, in any case, in Dan’s New York few could bring you down if you were a friend of Tammany. Tammany, founded by New York Democrats after the American Revolution, had been named in honor of a Delaware chieftain with a reputedly penetrating wisdom. It was initially a benevolent organization, but Aaron Burr used it as a political machine to support the election in 1800 of Thomas Jefferson as President and himself as Vice President. Members of Tammany were called braves, its officeholders sachems and sagamores. A grand sachem of Tammany, Martin Van Buren, had been elected President in 1836, but Tammany most prided itself on its potent influence over municipal elections and the appointment of civic officials. The sundry commissionerships and chiefships of the New York administration were in Tammany’s hold, as were the customs and treasury jobs that flowed from Democratic presidencies—the plums with which Tammany rewarded its children.

  The chief Wigwam of Tammany, Dan’s sacred and tribal site at Frankfort and Nassau Streets, featured at street level a large bar, a venue for factional meetings and less formal power-brokering, and the place in which a lively rank-and-file fueled itself before mass or general committee meetings. Upstairs was the large and ornate Council Hall, which, with the cultivated pretensions of its columns and chandeliers, was not a political environment for the easily cowed.

  Having begun as a sturdily Yankee organization, Tammany had become one that sought both to exploit and honor the Irish immigrant as a voter. In their secret hearts, some of the leaders might still despise Catholicism, but they needed the Irish adherents of Tammany to vote as an electoral legion. Many Irishmen of native wit, toughness, and cultivation rose high in Tammany and became close friends with Dan. He liked them for their intensity, their sense of tribalism, and their capacity to play factional politics as a great game, the best and most serious game of all.

  During Dan’s political career, the minions of Tammany Hall met most immigrant ships and sought to naturalize the newly arrived Irish through tame judges who were party clients. An Irish saloon at Centre Street printed 40,000 certificates to be handed out to its customers for presentation to the clerk of any of New York’s courts. These numbered tickets read, “Please naturalize the bearer.” And Tammany had other uses for the Irish. It fostered both community service and cohesion among its membership by creating “fire militias,” which served voluntarily in the tinderbox of the wooden tenements of Lower Manhattan. The fire militias also sponsored what were called target groups, whose members learned the use of firearms, and chowder clubs, more strictly social but designed to create an intensely loyal set of political paramilitaries for Tammany. These groups could operate without too much fear of the law, for the police force was also under Tammany’s thumb and patronage; to be a Tammany man was to stand a good chance of being admitted to the force.11

  The gangs of Tamman
y were notorious, whether fire militias or some less formal groupings. One gang leader, Captain Isaiah Rynders, a former New Orleans gambler and skipper of a Hudson River sloop, was a good friend and admirer of Dan’s and leader of the Empire Club, which New Yorkers commonly referred to as the Dead Rabbits. Rynders was the type of fellow who was present with his gang when votes were taken in Tammany for nominating conventions in favor of certain candidates. If necessary, he could arrange for extra voters to be brought in from Brooklyn or for ballot boxes favoring other candidates to be confiscated.12

  The friendships between Rynders and Dan and between Dan and more senior figures of politics and the legal profession were cemented by Dan’s lively wit and his quick intellect, but also by something more primal and male. These were the most important and closest connections of his life, perhaps surpassed only by his relationship with his father. He would support his network of friends within Tammany even to his own disadvantage, with a ferocious, uncritical fidelity.

  The fraternity of Tammany was, however, under stress as Dan established his new law practice, and the chief fault line was the same as that at the base of all American politics. The question was whether territories captured in the Mexican War should be free of the institution of slavery and involuntary servitude. The Democratic Party split into two factions over this issue. The Hunkers, including Dan and, at least by shared opinion, his father, wanted the new territories opening to the west to have the choice of being slave or free. The Barnburners wished to see slavery restricted to its present limits, and the West to be free of it.13