Sickles was no stranger to the law. As early as 1837, he was indicted for obtaining money under false pretenses. But after Lorenzo’s death, Sickles dropped out of school to study law under Benjamin F. Butler, a leading Democrat and attorney. Sickles passed the bar in 1843. During these years, he continued to gain a reputation for questionable practices. He was nearly prosecuted for appropriating funds from another man, was accused of pocketing money that had been raised for a political pamphlet, and charged with improperly retaining a mortgage that he had pledged as collateral on a loan. His exposure to Butler’s political connections, however, opened the door to a political career.4
His status as a lawyer, albeit one of questionable ethics, helped launch Sickles’ political career, which began in 1844 when he wrote a campaign paper for James Polk and became involved in New York’s Tammany Hall political machine. Sickles later liked to call himself “a tough Democrat; a fighting one; a Tammany Hall Democrat.” Not everyone was as impressed. “One might as well try to spoil a rotten egg as to damage Dan’s character,” scoffed New York diarist George Templeton Strong. Sickles’ political career was inextricably linked to stories about ballot tampering, theft, deceptive practices, and even brawls. One night, an angry mob burst into a Tammany meeting and threw him violently down a flight of stairs. (He managed to slow his fall by grabbing a banister and, although stunned and bleeding, was not seriously injured.) Still, his star rose, and in 1847 he was elected to the New York Assembly. He also found time for his only military association prior to the Civil War. As was common with prominent men of the era, Sickles joined the 12th New York State Militia in 1849, retiring from it in 1853 with the rank of major.5
Sickles continued to be active within the Democratic Party during the 1850s. He was a member of the Baltimore convention that nominated Franklin Pierce for the Presidency in 1852, and the following year he was appointed a New York City corporation counsel. Still a bachelor, he was gaining a reputation for fast and extravagant living. One contemporary admitted that Sickles “led the life of a very fast young man.” Money reportedly “poured through his fingers.” He became a “frequenter” of a Mercer Street bordello that was known as “the most select … and orderly establishment of a disreputable character in the city.” A prostitute named Fanny White ran the house, and according to her biographer, she reportedly “formed an attachment for Sickles and he became her protégé. It is stated that she paid his tailor’s bills, gave him jewelry to wear and kept him abundantly supplied with money.” While a member of the State Assembly, he was censured by his outraged colleagues for bringing her into the Assembly chamber. There were even rumors that he exchanged her services for campaign favors. If true, Dan Sickles may be Gettysburg’s only corps commander with “pimp” on his diverse resume.6
White soon learned that Sickles was bringing “his fascinating powers to bear on a certain Italian young lady” and, while in public one evening, White allegedly retaliated by beating him “unsparingly and unreservedly” with a heavy riding whip. White’s suspicions were accurate. The “young Italian” was Teresa Bagioli, whom the nearly thirty-three year old Sickles married in September 1852. The same girl Sickles had lived with when she was an infant was now a sixteen-year old student at a Catholic boarding school. Much to the objections of both his and her parents, they were married by New York’s mayor in a private civil ceremony. Why had a rising political star married a teenager? An anonymous family acquaintance later told the New York Times that “the consequences of this secret wedding soon made concealment impossible.” In other words, Teresa may have been pregnant. After eventually reconciling with their parents and the Catholic Church, a second ceremony was performed in March 1853 at the home of the Roman Catholic Archbishop. The exact date of their daughter Laura’s birth is unclear, but there is some contemporary suggestion that it occurred later in 1853, which would potentially leave the summer of 1852 (before the marriage) open as a conception date. There were also rumors of other children, which was not surprising given Dan’s reputation. One accusation held that Sickles was the natural father of James Gordon Bennett, Jr. In 1913, a New Jersey man named Alfred Molyneux had himself re-baptized as Alfred Sickles, and claimed to be an abandoned offspring of Dan and Teresa. Despite these colorful stories, history has recognized Laura as Dan and Teresa’s only child.7
Teresa’s pictures reveal an attractive dark-haired Italian. Six years into her marriage, as the wife of a congressman in Washington, she was described as “more like a school girl than a polished woman of the world” with a “sweet, amicable manner.” Conversely, while preparing Edgcumb Pinchon’s biography on Sickles, Pinchon’s researcher rejected the schoolgirl image, describing her instead as a “beautiful, voluptuous siren, without brains or shame” with a “lust for men” whom Sickles “loved to madness.”8
Now a member of Tammany Hall’s elite, in May 1853 Dan was offered a post as assistant to James Buchanan, the new American minister in London. Sickles initially declined the offer because the $2,500 annual salary “would hardly pay for my wine and cigars.” The initial rejection may have been simple posturing, for he soon reconsidered and won over Buchanan, who was impressed by Sickles’ “manners, appearance, & intelligence.” Sickles and Buchanan set sail for England in August 1853. Teresa did not initially accompany him (she was either in the late stages of her pregnancy or had a new infant to care for). Sickles did not travel alone, for the prostitute Fanny White apparently accompanied him.9
While in London, Sickles enjoyed wearing his New York militia uniform, and Buchanan did refer to him as “Col. Sickles.” Dan created an uproar, and embarrassed Buchanan’s diplomatic efforts, by refusing to participate in a toast to the Queen’s health on July 4, 1854. There were conflicting allegations that Dan brought Fanny to one of the Queen’s receptions and introduced the prostitute to Her Majesty. (An 1860 biography of White claimed that Fanny was “near succeeding it is alleged in obtaining an introduction.” Antagonistic New York papers, on the other hand, claimed that Sickles did successfully arrange the meeting.) By the time Teresa and new daughter Laura reached London in the spring of 1854, Fanny was back in New York. Teresa quickly became a favorite of Buchanan, a sixty-two year old bachelor, despite the fact that she was barely eighteen. Biographer Pinchon and his researcher were privately convinced that Teresa and Buchanan had an affair and that Sickles “understood it thoroughly, and worked the combination for all it was worth.” (Such a liaison would have been doubtful if Buchanan was a homosexual, as some historians believe.) Buchanan also became attached to his new aide, writing, “Sickles possesses qualifications … for a much higher place.” Although he admired Sickles’ abilities, Buchanan criticized Dan’s work habits, his handwriting (not a trivial complaint since this burdened Buchanan’s staff, who had to recopy Dan’s notes), and the fact that Sickles “spends a great deal of money.” In what would become one of Sickles’ lifelong habits whenever he was in a diplomatic assignment, he quickly grew tired of his role. “It would suit me better to stay away another year on account of the present condition of N.Y. politics,” Sickles wrote in June 1854, “but I am tired of London and of this mission.” Buchanan likewise was growing tired of Sickles’ preference for fast living over professional attentiveness, and they mutually agreed on Sickles’ resignation.10
Dan and Teresa returned to New York at the end of 1854, where it was evident that politics suited him better than diplomacy. He was elected to the New York State Senate in 1855, and was also named chairman of Tammany’s executive committee. Decades before he would help develop Gettysburg National Military Park, he organized a special committee that was instrumental in creating New York’s Central Park. Sickles did not create or champion New York City’s need for a great public park, but he helped consolidate advocates of the park, obtained consensus on a site, and assisted the governor in signing enabling legislation. His motives were not entirely pure, for he participated in a syndicate to purchase building lots near the park. Sickles freely admitted
as much: “I foresaw visions of fortune for myself and associates in the not far distant future, when the park should be established.” Ultimately nothing came of the syndicate, but to his credit he continued to pursue the park’s development. Sickles enlisted the help of New York friend Charles K. Graham, a surveyor and former navy midshipman who had helped construct the dry docks at the Brooklyn Navy Yard. Sickles had Graham make huge “before and after” drawings of the proposed park, which Sickles used to help steer the bill through the state legislature. Sickles’ influence was strictly political; writer Frederick Law Olmsted and architect Calvert Vaux won the park’s landscape design contest, and construction was not officially completed until 1873. So it was with perhaps some overstatement that Sickles would later watch thousands enjoy the park and proudly admit, “I have a fatherly feeling for Central Park.”11
In the spring of 1856, Sickles decided to run for Congress and help promote Buchanan’s bid for the presidency. In a speech on Buchanan’s behalf, Sickles espoused the Democrats as “the only party that professed and practiced justice to all men … [and] offered the only ground for the perpetuity and salvation of the Union.” Candidate Sickles was physically described as, “not stout but well knit together, complexion fair, eyes blue and expressive, mouth firm, and his general bearing … thoroughly indicative of … unflinching determination.” He wore a full drooping moustache. His contemporaries noted his “fondness” for women and, despite the fact that he was married and starting a family, was considered “somewhat of a lady-killer.” The ever-critical diarist George Templeton Strong thought Sickles belonged “to the filthy sediment of the [law] profession, and lying somewhere in its lower strata. Perhaps better to say that he’s one of the bigger bubbles of the scum of the profession, swollen and windy, and puffed out with fetid gas.” It is fair to conclude that Sickles did not receive Strong’s vote when he was elected to Congress in November by a wide margin, the same election that resulted in Buchanan’s elevation to the presidency.12
Sickles arrived in Washington for Buchanan’s inauguration in March 1857. That spring, before his first Congress even opened, Dan was lobbying to have Charles Graham appointed as civil engineer at the Brooklyn Navy Yard while simultaneously arranging to have the current holder of the position fired. Dan declined the incumbent’s challenge to a duel, but one morning the man burst into Sickles’ room at the Willard Hotel and began to whip the new Congressman with a cowhide. During the ensuing struggle, Sickles grabbed the whip and the man fled. The attacker published a note in a New York paper, claiming Sickles’ “whole career has been a series of unparalleled debaucheries. Graduating from the worst sinks of iniquity in this city, he has led the life of a professional vagabond. In debt to everybody … he stands before the public … a disgraced and vanquished man.” Graham got his job. Sickles’ New York enemies kept him in the papers even while he shifted his attention to Washington. In October 1857, he brought a libel action against James Gordon Bennett when the New York Herald accused him of stealing from the Post Office—a felony.13
Dan and Teresa set up their household on the prestigious Lafayette Square, across the street from the Executive Mansion, and President Buchanan was a frequent guest. The annual rent of the fine home was $3,000, or roughly equal to his congressional salary. In addition to Dan, Teresa, and daughter Laura, the large household included several servants. Washington wives played an important role in their husband’s careers, and Teresa had significant social obligations. She was expected to attend or host a party nearly every day and night. It was not uncommon for available bachelors to act as escorts for married women when their politician husbands were unavailable. Dan was frequently focused on his rising career. He would later admit that an active political career “forces a good husband to keep bad hours.” Good husband or not, Teresa suspected that his extramarital affairs had never really ceased.14
It was during this time that Sickles met Philip Barton Key. He was born in 1818, four years after his father Francis Scott Key penned “The Star Spangled Banner.” In 1853, Philip was appointed United States Attorney for the District of Columbia. He married in 1845 and had four children before his wife died in the 1850s. Although he was considered tall and athletic, he claimed that his wife’s death shattered his health. He was increasingly unable to attend to his professional duties and committed most of his work to assistant Robert Ould. Key’s inattentiveness was openly questioned following his inability to prosecute a California Congressman for murder in 1856. The New York Times later criticized Key as being “indolent and unread to a degree almost beyond belief in one filling such a position.” But his supposed poor health did not prevent his attendance at Washington parties. One hostess called him “the handsomest man in all Washington … he was a prominent figure at all the principal fashionable functions; a graceful dancer, he was a favorite with every hostess of the day.” It was also said that “no man in Washington was more popular with the ladies.” Key and Sickles were introduced through a mutual friend. The former was worried that Buchanan might replace him, and the latter agreed to intercede on his behalf; Key was reappointed to his position.15
Key and Sickles quickly became friends. When Sickles was traveling or attending Congressional sessions, which was often, Key accompanied Teresa to social functions. Gossip, quiet and limited at the outset, began to grow. When Sickles learned that a clerk was spreading rumors that Teresa and Key had spent time together at an inn, Dan confronted Key, who vehemently denied the charge. Key managed to have the terrified clerk retract his story. Calling it “ridiculous and disgusting slander,” Key convinced Sickles that, “Here’s an end to this nonsense.” In fact, Key was a liar, and he and Teresa were having an affair. Sickles would be labeled by future historians as “The Congressman who got away with murder,” but Sickles’ vantage point was somewhat different. He had given Key, a man who now owed his professional position to Sickles, an opportunity to personally own up to the affair. Key responded by lying and continuing to meet with Teresa. While Sickles was in New York, he asked a friend to “look in on” Teresa while he was away. When the friend and his wife stopped by the Sickles home unexpectedly one afternoon, they discovered Teresa and Key alone in a study with a half-empty bottle of champagne. Sickles’ household staff recalled another evening when Teresa and Key had remained locked in the drawing room until the early morning hours. Dan, meanwhile, won a bitter re-election fight that fall among accusations from his opponent of voter fraud and questions of how a Congressional salary supported such a lavish lifestyle.16
Key’s and Teresa’s romantic relationship heated up. The pair began meeting in a rented house on Washington’s Fifteenth Street, a poor neighborhood only two blocks north of Lafayette Square. Inquisitive neighbors began to notice an unusually distinguished-looking man and woman using the house. Key also took to signaling Teresa from Lafayette Square by waving a white handkerchief while standing across from the Sickles’ residence. He used a pair of opera glasses to detect her signals from inside the house.17
Unfortunately for Key, on February 24, 1859, Sickles received a letter signed by “Your Friend R.P.G.” The note told Sickles about the house on Fifteenth Street, which Key rented “for no other purpose than to meet your wife Mrs. Sickles. He hangs a string out of the window as a signal to her that he is in and leaves the door unfastened and she walks in and sir I do assure you with these few hints I leave the rest for you to imagine.” One can only imagine Sickles’ reaction. Unsuccessful in his previous effort at direct confrontation, the aggrieved husband undertook a more discreet course of action this time around. The next day, Sickles went to the House of Representatives, flung himself onto a sofa in a state of emotional pique, and asked clerk George Wooldridge to investigate. Wooldridge questioned Fifteenth Street residents as well as Sickles’ household staff. Convinced the rumors were true, he reported his findings to the congressman.18
On the evening of February 26, Dan extracted a full confession from Teresa. She admitted, in writing, to m
eeting with Key in the Fifteenth Street house. “How many times I don’t know … Usually stayed an hour or more. There was a bed in the second story. I did what is usual for a wicked woman to do.” Teresa also did “not deny that we have had connection in this house [the Sickles’ residence], last spring, a year ago, in the parlor, on the sofa.” To add insult to injury, “Mr. Key has ridden in Mr. Sickles’ carriage, and has called at his house without Mr. Sickles’ knowledge, and after my being told not to invite him to do so, and against Mr. Sickles’ repeated request.” Teresa admitted that the confession had been “written by myself, without any inducement held out by Mr. Sickles of forgiveness or reward, and without any menace from him.” Historians have speculated on why Dan had the written confession prepared. The most cynical interpretation is that he intended to use the confession as a defense in case of violence. A more reasonable assumption is that the shrewd attorney intended to use it in a divorce proceeding.19
The next day, February 27, was a warm Sunday afternoon. Unaware of Teresa’s confession, Philip Barton Key approached the Sickles house several times, slowly twirling his white handkerchief as an apparent signal for Teresa. Dan had summoned his friends George Wooldridge and Samuel Butterworth, an old Tammany Hall crony who happened to be in town. Butterworth arrived to find Dan “lying on his face on his pillow, overwhelmed with grief.” Suggesting that Dan’s first thoughts were for himself, he melodramatically told Butterworth, “I am a dishonored and ruined man. I cannot look you in the face!” Sickles eventually pried himself away from his couch long enough to spot Key. “That villain has just passed my house! My God, this is horrible!” Butterworth tried to calm Sickles down, but Dan was convinced everything was public knowledge and that “the whole town knew it!” As their story later developed, Sickles supposedly asked Butterworth to go with him to the clubhouse across the square, where Key held membership, and determine if Key had rented any rooms for illicit purposes. It was an odd request, given that Sickles already knew the couple used the house on Fifteenth Street. Butterworth supposedly agreed and walked out of the house, later insisting that he had no idea that Sickles intended to harm Key. Before following Butterworth, Sickles armed himself with a revolver and a pair of derringers.20
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