The army of repeaters sent to the polls on election day in 1868 was part of a desperate attempt to carry the state for both Tweed’s handpicked gubernatorial candidate, John T. Hoffman, and Democratic presidential candidate Horatio Seymour, who faced almost certain defeat at the hands of Republican war hero Ulysses S. Grant. Many came from outside Five Points to vote illegally in the neighborhood. Edward Cobb of Hester Street, for example, later admitted that for thirty dollars he voted the Democratic ticket fifteen or sixteen times, including at least once at Five Points’ Bayard Street polling place. Cobb reported that he saw Cuddy leading gangs of repeaters around the neighborhood that day. In many cases, Five Pointers invaded other districts to cast illicit ballots. Among them was James Clark of Mott Street, who testified later that for eight dollars he voted the Democratic ticket “eight or nine times in the 10th and 7th wards.”
But repeating was especially heavy in Five Points. One observer saw men at the polling place on Elizabeth Street just north of Bayard exchanging clothing with each other before going in to vote, either because they had already voted there or because they feared that a poll watcher might remember that they had cast ballots elsewhere earlier in the day. After depositing their ballots, the men went around the corner to the voting booths on Bayard, where a man furnished the repeaters with slips of paper listing the names and addresses they would use there. Others entering the polling place on Baxter Street also exchanged hats and coats with each other before casting their ballots.56
Why did Republican election inspectors acquiesce to such blatant fraud? Some were threatened with physical violence; others were drugged; still others had their registration books stolen. Some were probably bribed. And many who protested were simply ignored. In one Five Points election district, the Republican inspector tried many times to challenge voters he did not recognize as neighborhood residents. But his Democratic counterpart would snarl, “‘You be damned!’ and took the vote and put it in the box.” The Republican noted that as the day wore on and the crowds thinned, the Democratic inspectors would look at the registration book, copy down some names, and leave the room momentarily. A few minutes later, in would come a large group to vote upon those very names. Republicans who arrived late in the day to cast ballots often found their names had already been voted upon.57
All these facts came out in a congressional investigation in the winter of 1868–69. Yet the glare of public attention did nothing to curb the fraudulent voting. In fact, the number of votes cast in the Sixth Ward continued to escalate suspiciously, even though the subsequent elections were far less important than the 1868 presidential contest:
The number of ballots cast in the Sixth Ward increased 80 percent from 1867 to 1869, even though only one tenement was built in the district in that interval and others were torn down to make room for commercial buildings. The cities of Hartford and Providence, each with 50,000 inhabitants, did not cast as many votes in 1869 as did this single New York ward with only 21,000 residents. The 1870 census revealed that more ballots were regularly deposited in one Five Points precinct than there were men, women, boys, and girls living there. In other Five Points districts, there were more voters than adult male citizens eligible to cast ballots.58
Motivated in large measure by these revelations, Congress included provisions in two 1870 statutes that empowered federal officials to monitor and punish electoral fraud, though they could do so only in balloting for national office. The U.S. Attorney General consequently appointed lawyer John I. Davenport as a U.S. commissioner with wide-ranging powers to prevent and punish fraudulent voting in New York. Legislation enacted in 1871 and 1872 enhanced Davenport’s authority. The federal election inspectors who monitored balloting as a result of this legislation significantly diminished the illegal voting that had become so rampant in the Sixth Ward since the war:
The presence of federal inspectors scared away many repeaters, while others willing to vote repeatedly in the state contest would not do so in the national balloting for fear of arrest.59
Although federal legislation may have drastically reduced repeat voting, it did not deter Tammany entirely. Instead, the Democratic machine merely modified its tactics. If Democrats could not bring illicit voters to the polls, they would merely miscount those ballots that were cast. As usual, such practices were especially common in Five Points. Only 153 of the 283 registered voters visited the polls at 5 Mott Street on election day in November 1870. Nonetheless, Democratic inspectors announced that 280 votes had been cast—275 for Hoffman (in his bid for reelection as governor) and 5 for his Republican opponent—even though Republican poll watchers swore that at least thirty Republicans had cast ballots. In another Five Points precinct, inspectors reported that Hoffman had received 318 of 319 votes, prompting nine Republicans who had voted for his opponent there to write to the Sun asking what had become of their ballots. By focusing their fraud in Five Points, Tammany leaders further sullied the neighborhood’s reputation and established it in New Yorkers’ minds as the locus of Tammany’s electoral crimes.60
“MATT. BRENNAN IS NOT AN HONEST OFFICIAL”
Though Five Pointers continued to flourish in city politics, their ability to maintain their positions was increasingly dependent on the whims of “Boss” Tweed. Police Justice Joseph Dowling became an intimate Tweed ally—not a member of the Boss’s inner circle like Mayor A. Oakey Hall or Clancy’s mentor Peter Barr Sweeny, but an important supporter nonetheless. Dowling’s status was reflected in his selection (along with Hall and Sweeny) as a delegate to the Democratic National Convention in 1868. Jourdan, Dowling’s right-hand man, was appointed citywide superintendent of police in April 1870. Of the major Five Points politicians, only the Walsh brothers and Brennan remained aloof from Tweed. The Walshes actively opposed the Boss, refusing to cooperate with Tammany as long as Tweed controlled the organization. They were consequently frozen out of political office in the immediate postwar years. Brennan remained faithful to Tammany, though he kept his distance from Tweed. Yet in 1870, seeking a candidate with a reputation for honesty, Tweed acquiesced in Brennan’s nomination for county sheriff in return for his endorsement of the Boss’s candidates for mayor and comptroller. Brennan and the other Democrats easily carried the election.61
When Brennan took office as sheriff in January 1871, Tweed was at the pinnacle of his power. As a state senator representing the district that included Five Points, he had pushed through the legislature a new city charter that further entrenched his power. Tweed collected millions of dollars annually in kickbacks from contractors on city construction projects. He also collected obscene profits from businesses he owned that held city contracts. As president of the Board of Supervisors, Tweed and a fellow supervisor, Five Pointer Walter Roche (after whom the Roche Guard gang of the 1850s had been named), cooperated to demand payoffs from those who sought to have bills brought before that legislative body. Tweed was also assistant city street commissioner, and used that office to secure Roche the post of commissioner of street openings. Venal yet ingratiating, corpulent yet graceful, Tweed by 1871 ruled New York like Lorenzo de’ Medici. He dispensed jobs, bribes, and charitable donations—even food and shoes—to ensure a large and varied base of support while simultaneously using electoral fraud to maintain the sham that he and his regime were popularly elected. Few could resist his charms or defy his commands.62
Yet in selecting Brennan for the sheriff’s post, Tweed had sown the seeds of his own downfall. Brennan’s predecessor in the lucrative post, James O’Brien, apparently coveted another term in office. When Tweed spurned O’Brien’s efforts to secure the Democratic nomination (supposedly as punishment for O’Brien’s treachery in a factional dispute), O’Brien decided to seek revenge and began leaking evidence of Tweed’s crimes to the New York Times, which printed the revelations in July 1871. Tweed nonetheless stood for reelection to the state senate that fall, staying in the race even after authorities indicted him on civil fraud charges less than two weeks before the ele
ction.63
Fearing that a policeman arresting the Boss might bring him before Dowling or some other judge “in the Tweed interest,” prosecutors gave the warrants for his arrest to Brennan, who dutifully carried out the delicate task of arresting the most powerful man in New York. The forewarned press was on hand when, on October 27, Brennan entered Tweed’s office, tapped the apparently bemused Boss on the shoulder, and declared, “You’re my man!” Thomas Nast’s image of the scene for Harper’s Weekly contains the only known likeness of Brennan. Despite the apparently cool relations between the two men, Brennan did not make things too unpleasant for Tweed. The sheriff allowed the Tammany leader to begin his detention at a hotel owned by Tweed’s son, where the prisoner was given a spacious suite of rooms. Reporters arriving to interview Tweed found him “regaling himself in the apartments of his friend Judge Dowling,” who just happened to live in the adjoining suite. The Times later charged that Dowling kept several potential prosecution witnesses in jail on trumped-up charges in order to prevent them from testifying against the Tammany chieftain.64
Sensing Tweed’s vulnerability even before his arrest, Republicans had recruited as his opponent in the senate campaign Cork native Jeremiah O’Donovan Rossa, an Irish freedom fighter who had arrived in New York earlier in 1871 after the British released him and a half dozen other Fenian movement leaders from confinement in Tasmania. Tweed’s adversaries believed that the support Rossa might gain from the large Cork and Kerry populations in the Fourth and Sixth Wards could carry the revolutionary to victory, but on election night Tweed was declared the winner. In fact, Rossa apparently outpolled Tweed by 350 votes, but Tammany election officials “counted out” Rossa in order to perpetuate Tweed’s reign. The eccentric Rossa eventually became proprietor of a Five Points saloon “whose atmosphere,” according to one neighborhood historian, “seethed with hatred of Britain.”65
Meanwhile, Tweed’s empire began to collapse. In December, he was arraigned on criminal charges. Soon thereafter he was expelled from the Tammany Society and forced to resign his municipal offices. After two years of legal maneuvering, Tweed was finally convicted of fraud in November 1873 and sentenced to twelve years in prison.66
Sheriff Brennan, center, arresting Boss Tweed, October 27, 1871. Harper’s Weekly (November 18, 1871): 1084. Collection of the author.
Like all New Yorkers of modest means, Five Pointers viewed Boss Tweed’s demise with mixed emotions. One neighborhood saloonkeeper recalled a few years later that “the majority of people with whom I talked believe that the prosecutors of Tweed did wrong” in punishing him so severely. “Tweed has thousands among the poor today, who bless him. He kept the poor employed, and they would have done anything for him.” Jacob Riis found the same attitude toward the Boss still prevalent twenty years later. Tweed’s “name is even now one to conjure with in the Sixth Ward,” reported Riis. “He never ‘squealed,’ and he was ‘so good to the poor.’”67
Even though these statements probably exaggerated Tweed’s popularity in Five Points, neighborhood residents had benefited from the Boss’s reign in a variety of ways. Any Democratic leader would have supplied jobs to his most loyal political followers. Con Donoho had done so when Tweed was just a teenager. But under Tweed, such opportunities had expanded significantly. In addition, it was only when Tweed reached the height of his influence that the city’s Catholic churches, which for years had sought government subsidies for their parochial schools, finally received assistance. Five Points’ Transfiguration parish school received a grant of $11,500 in 1869 and slightly larger sums in each of the next two years before Tweed’s fall from grace, when such funding ceased.68
With Tweed’s indictment, his henchmen came under scrutiny, including his Five Points allies. In February 1872, Roche was arrested for absconding with funds from the bankrupt Bowling Green Savings Bank, of which he was vice president. The Times speculated that Roche might have been plundering the Bowling Green to save the Guardian Savings Bank, where the onetime saloonkeeper also served as vice president while Tweed acted as president. Roche had induced many Tammany politicos, including Brennan, to deposit large sums in the Guardian. By early 1874, however, Roche had still not been brought to trial, and he apparently never served any jail time.69
Despite his reputation for honesty and relative aloofness from Tweed, Brennan also came under suspicion as the Tweed Ring collapsed. Even before Tweed’s indictment, the Tribune published a series of reports charging that the sheriff’s Ludlow Street jail levied outrageous fees on prisoners, keeping the proceeds for himself and his cronies. Brennan also apparently inflated the bills he submitted to the city for making arrests and seizing goods. In one such case, he charged the city $419. After complaints by the defendant, a judge in November 1872 examined the sheriff’s actual expenses and reduced the fee to $19. Month after month, the Times published editorials condemning “Brennan’s blackmail” and excoriating the Five Pointer for his “career of plunder.” One case of “plunder” involved Monroe Hall, the building that housed Brennan’s saloon. In 1863, Brennan had signed a ten-year lease to rent part of the building to the Second District Civil Court for an outrageous $2,800 per year. When Tweed Ring plundering reached its height in 1870, charged the Times, Brennan had had the audacity to have the board of aldermen annul that agreement and increase the rent to an astounding $7,500. “MATT. BRENNAN,” the Times solemnly concluded, “is not an honest official.”70
Brennan tried desperately to maintain his position in city politics and the Democratic party. In theory, Tweed’s downfall might have helped Brennan advance, inasmuch as the Boss and his Ring leaders had all either been indicted or fled the country. Yet Brennan was never able to win acceptance from the “reform” wing of the party headed by “Honest John” Kelly either, especially as the press continued to condemn the extravagant fees levied by his sheriff’s office. In the fall of 1873, the Times reported gleefully that Brennan had failed to get his handpicked choices selected to represent the city at the Democratic state convention. A few weeks later, his candidate for state assembly also lost a primary battle. Brennan himself was denied renomination that fall, as Tammany chose a slate of reform candidates associated with Kelly that included William Walsh as the nominee for county clerk. Brennan would have to serve out his remaining days as sheriff as a political outsider.71
In the end, Brennan’s involvement with the Ring did land him in jail, though not for the reasons one would expect. Just before Christmas 1873, with only a few days remaining in Brennan’s term, Tweed associate Henry W. Genet was convicted of stealing city building supplies and funds by submitting fictitious work vouchers. Genet, whom the Times later called “one of the most vulgar, brutal, and defiant of the Ring conspirators,” was remanded to the custody of William H. Shields, Brennan’s chief deputy and husband of his favorite niece. Shields, as he often did with prominent convicts, allowed the prisoner to enjoy himself in the short interim until his sentencing. A month earlier, Shields had offered the same privilege to the convicted Tweed, who had spent each of the three days before his sentencing with the “Stable Gang” of politicos who congregated at a Five Points livery stable. Shields allowed Genet to attend a gala “going away” party in his honor at which virtually every important city Democrat made an appearance. Before escorting Genet to his sentencing on December 22, Shields allowed him to return home for a last visit with his wife. While the deputy sat unsuspectingly in the parlor, “Prince Hal” escaped out a back window. Within hours, he was on his way to Canada, and from there he set sail for Europe. For allowing Genet to escape, the incensed trial judge fined Shields and Brennan $250 each and sentenced them to thirty days in jail. On January 8, 1874, just a few days after stepping down as sheriff, the humiliated Brennan returned to the Ludlow Street jail he had presided over for three years, this time as a prisoner.72
Brennan’s ensuing decline was remarkably swift. Breen recalled that Brennan, “a very proud man, was then getting old, and was so deeply mortified b
y his imprisonment and the abuse he received from the public press that he never recovered his former self. After getting out of prison he kept to his house, and although up to this episode he was one of the most popular men in New York, he never again took any further interest in public affairs.”73
“AN ERA IN NEW-YORK POLITICS SO ENTIRELY
OF THE PAST THAT IT SEEMS LIKE ANCIENT HISTORY”
“Mr. Brennan was the product of an era in New-York politics so entirely of the past that it seems like ancient history,” asserted the Times when it announced that Brennan had died on January 19, 1879, at age fifty-six. The Times was right. Ward primaries were no longer decided by knockdown, drag-out brawls. Polling places were no longer dominated by gangs seeking to prevent certain voters from casting their ballots. Service in the police or fire departments was no longer a prerequisite to political advancement. And gone were the days when Irish Catholics were all but barred from citywide offices.74
The old era of New York politics also seemed a thing of the past because while Brennan died young by modern standards, he had outlived almost all of his Five Points political contemporaries. Yankee Sullivan committed suicide in a San Francisco jail cell in 1855 while in his late forties. Clancy died during the Civil War at thirty-five. Jourdan passed away suddenly in 1870 at thirty-nine, only a few months after becoming the city’s police superintendent. McCunn, whose naturalization frauds were just a few of his many crimes, was impeached and removed from office by a unanimous vote of the state senate on July 2, 1872. Literally mortified, McCunn died at age forty-seven just four days later. William Walsh passed away prematurely as well, in March 1878 at age forty-two, soon after completing his term as county clerk. Tweed died in jail a month later at fifty.75
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