Heir to the Empire City

AS TWENTY-THREE-YEAR-OLD Theodore Roosevelt boarded the train for Albany on January 2, 1882, he could not have imagined that he was embarking on a forty-year career in politics. For the next three years in the New York Assembly representing his New York City district, Roosevelt would receive an education in the intricacies of state and local politics. He would lock horns not only with Democrats, but also with his own Republican leaders. He would take on the Tammany boss of New York, and he would publicly interrogate the city’s mayor. Roosevelt chaired investigations, gave speeches, and wrote legislation. He also learned the power of the press, befriending the Albany correspondent of the New York Times and becoming the focus of headlines and favorable editorials. Through it all, Roosevelt would grapple with the challenges of how to make America’s largest city more livable.

As his train moved slowly along the Hudson River, Roosevelt also followed an uncertain path. William Waldorf Astor had lost his bid for Congress. Could the silk-stocking Roosevelt really make headway among the hacks and lobbyists in Albany? Could he really make a difference in the Republican Party, even as he claimed his independence? The next three years would prove crucial in shaping the savvy Republican politician Roosevelt would become.

FOR ANYONE PAYING attention, that second day of the year—and the coldest day of winter so far—held a lesson in city and state politics. Following cues from their boss, “Honest” John Kelly, and in a snub to their party’s choice for Senate president, Tammany Democrats in the legislature refused to caucus. In New York City, Kelly scored a victory by getting his man William Sauer elected president of the Board of Aldermen, a body that had great control over departmental appropriations and mayoral appointments. In his message to the board, Mayor William Grace lamented the fact that the city had over $135 million in debt, the largest municipal indebtedness in the United States. Grace blamed past “extravagance and misgovernment” by the “plunderers of our City.” Sauer’s election as president was a blow to the mayor, whom Sauer had repeatedly denounced as a liar. The president of the Board of Aldermen also served on the Board of Estimate and Apportionment, which would advise the mayor on all departmental appropriations for the coming year. Since the Board of Aldermen also had the power to confirm or reject the mayor’s appointments, Sauer and Tammany Hall would thus have control over much of New York City’s government. It was understood that candidates for city jobs regularly paid Tammany Hall for its support and then pocketed city money once they received their appointments. No wonder New York City had a debt equivalent to about 10 percent of the total evaluation of all Manhattan real estate.

While Democrats in Albany wrestled with Tammany obstructionism, Republicans continued to split along the lines of the factions that plagued the party nationwide. With Garfield’s assassination and Arthur’s ascension to the presidency in September of the previous year, Stalwarts seemed to have scored a victory. But the many-sided divisions within the party—Stalwarts, Half-Breeds, and independent reformers—meant that no single faction could gain the balance of power. These party divisions had played themselves out in city and state elections across the country as Republican factions battled each other. The results would be reflected in the midterm congressional elections of 1882—a Democratic rout of Republicans. Closer to home, New York had seen the drama of Republican factionalism played out in a battle between the state’s two US senators and President Garfield, when Roscoe Conkling and his lieutenant, Thomas Platt, had resigned their Senate seats to protest Garfield’s appointment of a Conkling foe, William Robertson, to the post of collector of the New York Custom House. Robertson had led the Blaine forces of New York during the 1880 convention, and Blaine had worked to prevent Conkling’s reelection, ending the flamboyant boss’s career and influence. Platt’s seat was taken by a new leader in New York politics, Warner Miller, a Blaine man who would soon cross swords with a young maverick assemblyman named Theodore Roosevelt.

These Republican factional divisions could be found even at the state party caucus. The divisions resulted from the 1880 Republican National Convention, when the Stalwarts had backed former President Grant for a third term, while the Half-Breeds had advocated the nomination of James Blaine. When gathering to choose a candidate for Speaker of the Assembly in January 1882, the Stalwarts preferred George H. Sharpe of Ulster County, while the Half-Breeds backed Thomas G. Alvord of Onondaga County. Alvord, known as “Old Salt,” was over seventy years old and had a political career reaching back before the Civil War. He had served as Speaker several times, the first being in 1858, and had even been lieutenant governor. Sharpe’s career seemed to have crossed paths with every prominent American since the Civil War. During the war he had served on the staffs of Union generals Joseph Hooker, George Meade, and Ulysses S. Grant. As assistant provost marshal at the end of the war, Sharpe was responsible for paroling 28,000 Confederate soldiers, including Robert E. Lee. In 1867, Sharpe traveled to Europe at the request of Secretary of State William Seward to track down and return to the United States John Surratt, son of Mary Surratt, who had been hanged as one of the conspirators in Lincoln’s assassination. By 1877, Sharpe was serving under Chester Arthur in the New York Custom House. As surveyor, Sharpe was one of the officials whom President Hayes had tried to remove as he took on Conkling and the Republican machine by appointing Theodore Roosevelt Sr. to replace Arthur. Hayes was unsuccessful, and Sharpe continued to serve under Collector Arthur, and alongside naval officer Alonzo Cornell, who was now governor. That episode, only a few years prior, had been an excellent primer on New York politics for Harvard undergraduate Theodore Roosevelt Jr.

In the contest between Alvord and Sharpe, one Stalwart and one Half-Breed, the recently elected Roosevelt found himself among those independent Republicans who didn’t like either one. This reflected exactly the position of many New York and New England Republicans in the years between 1880 and 1884. In his diary, Roosevelt called Sharpe “a man of ability and shrewd enough to recognize the advantage of being considered respectable, but unless I am mistaken decidedly tricky and unquestionably a machine man pure and simple.” Roosevelt was absolutely right, as Sharpe was a key lieutenant in the state Republican machine. But, just as many independents had rejected the candidacy of corrupt Half-Breed James Blaine in 1880, Roosevelt could hardly stomach Alvord: “a bad old fellow.” Roosevelt lamented the “choice of evils” he faced. In the end, he chose Sharpe. The party chose Alvord. This would be the first of many times Roosevelt bucked the trend of his party and defied the wishes of party leaders such as Warner Miller and Thomas Platt.

With Republicans in the minority in the Assembly that year, their choosing Alvord appeared to be little more than pro forma. Democrats held the majority and would name the Speaker. But as the Tammany snub of the Democratic caucus on the same day indicated, John Kelly was not happy. In 1880, Kelly had helped elect William Grace as the first Irish American, Catholic mayor of New York, only to have Grace turn against Tammany. Now Tammany and anti-Tammany Democrats fought their battle in Albany. Only seven Tammany men from the city had seats in the Assembly, but that was enough. With Democrats holding 67 of the 128 Assembly seats, and Republicans holding 61, those seven Tammany seats held the balance of power. It was the power to obstruct. Roosevelt’s first month in the Assembly was spent watching the Tammany men cast votes for their own candidate for Speaker—if they showed up at all—preventing a majority vote and stopping all work. This empty time allowed Roosevelt to observe his fellow members and draw conclusions he would hold for the rest of his career. He had few compliments for the Republican leaders, but he truly despised those Democrats whom he called “the City Irish.” Roosevelt labeled them “vicious, stupid looking scoundrels with apparently not a redeeming trait, beyond the capacity for making exceeding ludicrous bulls.” Roosevelt’s reference to “bulls,” papal decrees, reflected the typical anti-Catholic sentiment of his class.

Day after day, the absurd deadlock in the Assembly perpetrated by the Tammany Democrats continued. Roosevelt described one of the Tammany men, named Bogan, as “a little celtic liquor seller, about five feet high, with an enormous stomach, and a face like a bull frog.” Roosevelt then related an exchange between Bogan and the clerk. “I rise to a pint of ardther (order) under the rules!” Roosevelt recounted in his diary, mimicking the man’s Irish accent. “There are no rules,” the clerk replied. “Then I object to them!” “There are no rules to object to,” the clerk repeated. “Indade! That’s quare, now; (brightening up, as he sees a way out of the difficulty) Very will! Thin I move that they be amended till there ar-r-r!” Despite his anti-Irish overtones, Roosevelt certainly had a knack for description, whether it was a cow-bird in the Adirondacks or a Celt in the Assembly he was portraying. And Roosevelt’s mimicry of the Irish brogue foreshadowed the farcical writings of Chicago journalist Finley Peter Dunne and his character Mr. Dooley. Years later, when “Mr. Dooley” wrote a mocking review of Roosevelt’s The Rough Riders, he concluded, “If I was him I’d call th’ book, ‘Alone in Cubia.’” Roosevelt loved it, and Dunne became a frequent guest at the White House.

Roosevelt’s harangue against assemblymen of Irish descent confirmed not only his own class and ethnic prejudices, but also his political prejudices. “The average catholic Irishman of the first generation as represented in this Assembly, is a low, venal, corrupt and unintelligent brute,” Roosevelt wrote in his diary. He perceived a great contrast between the Republican and Democratic lawmakers. The Democrats were represented by the rougher urban classes and included liquor sellers and a pawnbroker. The Republicans, in contrast, were mostly lawyers or farmers.

Within a few weeks, Roosevelt was able to widen his understanding of his fellow legislators and see them in a broader context. Namely, he caught sight of the strings that manipulated the Tammany men, strings that stretched back all the way to Manhattan. “Of course such a hopelessly ignorant set of men as these Tammany members are can not do their own thinking,” he observed. “They are managed entirely by the commands of some of John Kelly’s lieutenants who are always in the Assembly chamber.” County Democrats were little better, and were whipped into line by a New Yorker whom Roosevelt would soon target in his Assembly investigating committee. Roosevelt observed that Commissioner of Public Works Hubert O. Thompson, although filling a key post in the New York City government, spent most of his time in Albany. “He is a gross, enormously fleshy man, with a full face and thick sensual lips,” Roosevelt wrote with characteristic descriptive flair. Thompson, he continued, “wears a diamond shirt pin and an enormous seal ring on his little finger.” Thompson also kept several hotel parlors stocked with champagne and free food for assemblymen, lobbyists, officeholders, and party bosses. The question must have come to Roosevelt’s mind: Where did Thompson get so much money for such a vulgar and ostentatious display of wealth? As the city department head responsible for building and maintaining New York’s entire infrastructure, Thompson managed an enormous budget of millions of dollars. It would become Roosevelt’s quest to root out corruption in Thompson’s department, targeting the “wire-puller,” or political operator, directly.

As the Tammany deadlock wore on, some Republicans became impatient and proposed throwing in their lot with the regular Democrats. In a crucial moment of insight, Roosevelt opposed such a move, understanding that a split Democratic Party could only aid Republicans. Perhaps he remembered the criticism of President Hayes for splitting the Republicans during the custom-house battle in 1877. Roosevelt wrote, “I consider it no part of ours to interfere in a family quarrel, it being a very pretty fight as it stands.” Just as Roosevelt early on delighted in seeing the Democrats hopelessly split, for the rest of his career he would despair watching Republicans split along factional lines and go down to defeat at the hands of the Democrats. Still, some Republicans wanted an end to the deadlock for the sake of getting on with the job of passing legislation. Roosevelt thought this absurd and rose to say so in his first speech to the legislature. As the Times recounted in an article on the Assembly’s fourth week of “unorganized existence,” Roosevelt said in his speech that while the stalemate among Democrats might be a hindrance to legislation, “he has talked with a number of representative manufacturers and business men, and he was satisfied that they could get along quite nicely on their present allowance of legislation. [Laughter.]” It was a clever and pithy first effort, which, as Roosevelt noted in his diary, “was very well received.”

Finally, on February 14, Valentine’s Day, and a date that would come to haunt Roosevelt, the Democrats reconciled and elected a Speaker. Significantly, Roosevelt was assigned to the Cities Committee—“just where I wished to be,” he wrote. As cities in New York State did not enjoy home rule, the Cities Committee was the most important organ for making laws affecting New York City. After Roosevelt’s appointment, he quickly introduced four bills. The topics of these bills ranged from the city’s finances to its drinking water, showing the range of challenges facing American cities in the late nineteenth century. The bills also included one to reform the organization of the Board of Aldermen, an unelected and shadowy body that sat in the pockets of the city bosses and was able to curb mayoral power. At that very moment in New York, Mayor Grace was battling with the board and its new president, Sauer, who took his orders from Tammany boss Honest John Kelly. Roosevelt hoped the bill would do away with such “dickering.” This was putting it mildly, as Roosevelt would soon find out. More than just dickering, aldermanic control over budgeting and mayoral appointments represented a critical nexus of corruption in New York City’s government. Until the day he stepped down from his Assembly seat three years later, Roosevelt would continue to view reforming or abolishing the Board of Aldermen as key to cleaning up New York’s corrupt city government.

DURING THAT SAME first, one-year term in the Assembly, Roosevelt championed the impeachment of New York Supreme Court Judge Theodore Westbrook. Westbrook had been publicly accused of helping depress the value of Manhattan Elevated Railway Company stock to allow its acquisition by the notorious financier Jay Gould. Roosevelt took keen note of the fact that three months after the accusations had been made in the press, Westbrook still had not professed his innocence. Roosevelt called for a bill empowering the Assembly’s Judiciary Committee to investigate Westbrook, thus taking on powerful interests while still only a freshman legislator. In the end, little came of the investigation, which did not involve Roosevelt’s Cities Committee, and the majority report largely absolved Westbrook. Yet in defeat Roosevelt had achieved much, and perhaps learned even more. Roosevelt had made a name for himself throughout the state as a bold reformer, thus earning the loyalty of many other young, reform-minded men at Albany. He had given rousing speeches in the Assembly, including chastising his fellow legislators for letting Westbrook off the hook. “You cannot cleanse the leper,” Roosevelt admonished. “Beware lest you taint yourselves with this leprosy.” Finally, he had learned the power of the legislative investigating committee to uncover lurid backroom deals, the details of which could fill the press and inflame the public.

Roosevelt won reelection in 1882 in the face of, as he noted, a “Democratic Deluge” that elected Democrat Grover Cleveland governor of New York and further reduced the Republican minority in the legislature. With Democrats firmly in power, Republicans had little hope of passing significant legislation. In a nice nod to Roosevelt, fellow Republicans nominated him for Speaker, the de facto minority leader. Not everyone approved. The Stalwarts bitterly fought Roosevelt’s selection, while independents backed him. Roosevelt noted that he got along well with the country Republicans, mostly farmers and storekeepers, “shrewd, kindly, honest men” who also happened to be “native Americans” rather than Irish. Roosevelt continued his differentiation between “native” Americans and those assemblymen who were immigrants or sons of immigrants. Moreover, from this point in his career onward, Roosevelt’s strength would often be found among upstate Republicans. As an independent reformer from the city, Roosevelt frequently battled with city Republicans who viewed his frequent crusades with skepticism if not downright hostility.

During his second year, Roosevelt continued his education as an urban reformer. He helped usher through the Assembly a bill forbidding the rolling of cigars by residents of New York tenements, a filthy job that exacerbated the already horrific conditions inside the tenements. When the bill came before Roosevelt’s Cities Committee, he was named one of three members tasked to investigate the problem. He was then approached by the local union representative, Samuel Gompers. When Gompers described the conditions in the tenements, the brown-stone-born Roosevelt did not believe the labor leader. Only after Roosevelt took three tours of the tenements did he come away shocked at what he saw. Writing in his Autobiography nearly three decades later, he could still vividly evoke the harsh conditions in which New York’s working poor lived. “The work of manufacturing the tobacco by men, women, and children went on day and night,” Roosevelt observed, “in the eating, living, and sleeping rooms—sometimes in one room.” In one tenement he visited, two families occupied one room. They had even taken in a male boarder, who slept on whatever patch of ground was available. Tobacco could be seen everywhere, stored alongside the stained bedding and in a corner where bits of food had fallen. Roosevelt was revolted. When the bill reached Governor Cleveland’s desk, Gompers asked Roosevelt to champion the bill to the skeptical governor. Roosevelt did so, acting not only as spokesperson for the labor leader and unions, but, as Roosevelt saw it, also for the exploited immigrants and tenement dwellers. Cleveland signed the bill.

A photo taken of Roosevelt in Albany that year shows the twenty-four-year-old surrounded by some of his closest colleagues in legislative work, including Walter Howe, Isaac Hunt, and William O’Neil. In his diary, Roosevelt noted that the four of them always sat together—“a pleasant quartette.” Significantly, seated at the center of the photo is the legislative correspondent for the New York Times, George Spinney. Roosevelt’s Albany experience began a long career in which he cultivated good relations with the press. As equally Republican and reform-minded as Roosevelt, the New York Times was usually a dependable ally and supporter of his efforts. In March 1883, the Times praised Roosevelt’s “rugged independence”: “Whatever boldness the minority has exhibited in the Assembly is due to his influence, and whatever weakness and cowardice it has displayed is attributable to its unwillingness to follow where he led.” Roosevelt was making important allies as a reformer. The question was: Could Roosevelt also champion causes that would win him friends among the party’s leadership? The year 1884 would provide key answers.

Before his successful bid for reelection in November 1883, Roosevelt made a life-changing trip west to hunt buffalo. He had already dipped his toe in the Dakota Territory on that pre-wedding trip west with Elliott in the fall of 1881. When he returned two years later, in autumn 1883, he traveled further west, to the Little Missouri River and the border of Montana. But for Roosevelt, with this first glimpse of the Badlands, more than just the geography had changed. By the early 1880s, books, articles, and even government reports were calling Montana and Dakota ready for a cattle boom, with beef barons claiming returns in excess of 50 percent. Roosevelt had even invested $10,000 in the Teschmaker and Debillier Cattle Company, which ran a herd north of Cheyenne. In 1883, Roosevelt indicated in his accounts an income of $500 from that investment, a return of 5 percent. At the same time, Roosevelt had made large investments back east. He put $20,000 in his publisher, G. P. Putnam’s Sons, and had bought ninety-five acres of land on Oyster Bay, where he would soon start constructing a home for himself, Alice, and their expected brood of children. He had even contemplated buying a farm in the Adirondacks, scene of his youthful birding trips. By the fall of 1883, Roosevelt was on the lookout for several things: an investment that would provide him with a healthy and regular annual return; a nice piece of working agricultural land that would also afford him the enjoyment of outdoor life and opportunities for hunting; and an active, healthy, part-time occupation that would balance his more sedentary pursuits of politics and writing. No wonder that on that first trip to western Dakota, Roosevelt was primed to make a snap decision, one that would have large personal and financial ramifications for him. With a handshake and a personal check, Roosevelt returned to New York and his seat in the Assembly having invested one-third of his net worth in two cattle ranches.

ROOSEVELT’S FINAL SESSION in the Assembly in 1884 promised to be his greatest. It began badly. Republicans had regained a majority in the Assembly, and Roosevelt was up for the position of Speaker. Beginning in the fall of 1883, Roosevelt had written to fellow Assembly members soliciting their support. When Jonas Duzer of Chemung County inquired as to which faction, Half-Breed or Stalwart, Roosevelt belonged, Roosevelt replied, “I am a Republican, pure and simple, neither a ‘half breed’ nor a ‘stalwart’; and certainly no man, nor yet any ring or clique, can do my thinking for me.” This was classic Roosevelt, but it was an attitude that would hardly endear him to party leaders. Moreover, 1884 was a presidential election year. There was simply no way the Republican bosses could have allowed the independent Roosevelt into such a prominent position. Roosevelt lost the race for Speaker when the Republican machine, led by Senator Warner Miller, engineered his defeat. Instead, Roosevelt had to be content with the chairmanship of his Cities Committee and of a special committee to investigate corruption in New York City, namely, in Hubert Thompson’s Department of Public Works.

At the opening of the new Assembly in January 1884, Roosevelt introduced three bills that indicated how reform of New York’s municipal administration might be achieved. The first bill—called the “Aldermanic” or “Roosevelt” bill—would give the mayor complete power, without reference to the unelected aldermen, to appoint department heads. The model for Roosevelt and the other reformers in framing the bill was Brooklyn, where a similar law had invested Mayor Seth Low with sole appointing power. The result seemed to be better department heads and more public interest in municipal politics, with a visible and more powerful mayor. Indeed, in Brooklyn, more people voted for mayor than voted for governor. Roosevelt’s second bill called for limiting municipal indebtedness. New York City’s debt had increased more than tenfold over the previous quarter century, fueled by massive public works projects that also made many politicians rich. His third bill, finally, sought to break the Tammany Hall–saloon axis by establishing a high license fee to sell liquor in the city. The first two bills would eventually be passed, with the bill concerning the mayor’s power of appointment labeled by the press the “Roosevelt Bill.” The license bill failed, but it presaged the time when Roosevelt, as president of New York’s Board of Police Commissioners, would again go after the corrupt alliance between politicians and saloon owners.

Roosevelt achieved more immediate success when the Assembly voted to establish a special committee to investigate New York City government. Roosevelt was named chairman of what came to be known as the “Roosevelt Committee.” His associates on the committee were two Republicans, including his good friend William O’Neil, and two Democrats who were largely sympathetic to Roosevelt. The resolution specifically targeted the Department of Public Works under Commissioner Hubert O. Thompson, under whose management its annual expenditure had risen 65 percent, or almost $5 million, from only the year before. Taxes in the city had meanwhile risen by only about $3.5 million. The resolution also noted that the Union League Club and the city press had charged Thompson with fraud and that, in general, the public demanded an investigation of a city government notorious for corruption. Here was Roosevelt championing the reform elements of New York’s press and Republican Party. And by targeting the Democratic city government, Roosevelt also pleased machine Republicans. When Roosevelt could figure out how to please both kinds of Republicans simultaneously, he achieved his greatest successes.

The committee met for the first time in the Metropolitan Hotel in New York City on January 19, only four days after the Assembly passed the resolution. Roosevelt and his fellow committee members would gather in the city three days a week, on Fridays, Saturdays, and Mondays, which allowed them to return to Albany for the rest of the week. This was a very busy time for Roosevelt. He was chairing his Cities Committee in Albany, writing and championing bills in the Assembly, and commuting to Manhattan for his committee hearings as well as attending to his very pregnant wife. The hearings themselves displayed Roosevelt’s growing political acumen at only age twenty-five. As chairman, Roosevelt had to deal with hostile witnesses and their counsel, obdurate members of his own party, the mayor of New York, and even the Tammany boss, John Kelly. All the while, Roosevelt ensured a constant stream of sensationalist testimony to the press and public.

Although Roosevelt had been successful in calling for an independent Assembly investigating committee, the New York Senate had convened its own investigating committee, which was holding hearings simultaneously in the mayor’s private office in City Hall. The Senate, too, was very interested in hearing from Commissioner Thompson, and had left a subpoena for him in his office at the Public Works Department. Perhaps foreseeing a conflict with the Senate, Roosevelt had personally gone to see Thompson and secured a promise from him to appear before the Assembly committee. Thompson fulfilled his promise to Roosevelt, ignoring the Senate subpoena. The questioning of Thompson had barely begun when a messenger interrupted the proceedings and handed Thompson a telegram from his counsel demanding his appearance before the Senate committee. Laughing, Thompson read the telegram to Roosevelt and his colleagues, and then he loudly told the messenger, seemingly for the benefit of his audience, “Tell them I will leave here in five minutes,” a dismissive comment that drew laughter from those assembled. Roosevelt must have been displeased to be outmaneuvered by the chief target of the investigating committees. It was an inauspicious beginning.

The comedy of errors and evasions continued. The register, John O’Reilly, whose office was responsible for recording all property transactions in the city, had only been in office for three weeks and could offer little information, and his predecessor had gone to Cuba “on the advice of his physician.” Cuba was a favorite of New York politicos fleeing investigations and prosecution, as witnessed by William Tweed’s flight there in 1875. Next, the committee called the county clerk, Patrick Keenan. Keenan was the exact sort of politician that Roosevelt and other reformers wanted to target: Keenan was a former alderman, a former liquor dealer, and, of course, a Tammany man. Keenan readily admitted to the committee that he had paid $7,500 to Tammany Hall for his nomination, and had kept about $14,000 in fees paid to his office. Yet, apparently, Keenan knew very little about what his office actually did. He spent little time there, instead leaving the office in the care of his deputy. As he explained to the committee, “a man in the city of New York who is considered a local politician—they have a great many things to attend to sometimes and they can’t attend to the business at all times.” This led Roosevelt to ask, “Do I understand you to mean that your duties as a local politician occasionally override your duties as clerk?” Keenan was typical of machine appointees: they paid for their posts and pocketed departmental fees and expenses, simply padding their income from their normal business, frequently a saloon. For municipal reformers such as Roosevelt, Keenan perfectly reflected the corruption that made Tammany men rich while beggaring the city.

The committee then turned its attention to the Ludlow Street City Jail and its boss, the sheriff. One of the first things that Sheriff Alexander Davidson disclosed about the running of the jail was that he personally owned the van and team of horses used to transport prisoners. The fact that he had bought the team from his predecessor indicated that this was a moneymaking scheme handed from one sheriff to the next. When asked about the cost of the van and horses, Davidson replied, “Is that not a matter of private affair?” Roosevelt replied, “It is not a matter of private affair; we want to find out if the fees of this office are or are not excessive; therefore, we want to find out what the cost of your plant is.” When the sheriff continued to claim it was a private affair, Roosevelt showed a flash of anger. “You say you consider that a private question,” Roosevelt began. “The committee radically disagrees with you; you are a public servant, you are not a private individual; we have a right to know what the expense of your plant is; we don’t ask for the expense of your private carriage that you use for your own conveyance; we ask you what you, a public servant, pay for a van employed in the service of the public; we have a right to know; it is a perfectly proper question.” Davidson noted that his office also hired private carriages, or “hacks,” to convey prisoners, including convicted murderers. When asked about the cost of hiring a carriage, the sheriff replied, “It depends entirely upon the generosity of the person who owns the hack. . . . When a deputy sheriff is handcuffed to a criminal, he is not apt to stand long for a dollar or two dollars.”

Even the execution of prisoners seemed to be a moneymaker for the sheriff and his deputies, twenty of whom were paid to oversee a single execution. When asked about the necessity of having twenty deputies attend an execution, the sheriff replied that he was authorized to keep the peace. But, it was pointed out, the executions took place inside the presumably secure prison: “Why is it necessary to have twenty persons inside of the prison, twenty deputies to attend an execution?” The records also indicated a large fee of over $390 paid to Michael McGloin and Pascal Majone. Asked about this expense, Sheriff Davidson replied, “It is a contract that I make between the party that cuts the rope [for the hanging] and myself.” The counsel for the committee, Charles Miller, began to ask the name of the person who cut the rope, but Roosevelt, seeing the real point of attack, cut him off. “You need not ask that,” he said, then turned back to Davidson: “You pay $396 to the party that cuts the rope?” When both the sheriff and his counsel defended the expense, Roosevelt lectured them: “Mr. Sheriff, it is perfectly true that there is no occasion for squeamishness in answering a question like this; the occasion for squeamishness would be in taking advantage of your position for charging too much for things like this about which you think no inquiry would be made.”

The investigation into the jail continued, with the sheriff’s clerk, Jacob Wertheimer, and the undersheriff, Joel Stevens, called to testify about topics that included the practice of overcharging the city for a prisoner’s stay in the jail and the cost of transporting prisoners. At the end of testimony on February 1, Wertheimer was arrested on the charge of collecting in the name of the sheriff, in 1883, at least $5,000 to which the sheriff was not entitled. The New York Times, which reported the committee hearings with great interest and sympathy for Roosevelt, noted almost in passing how Tammany had come to the rescue of one of its own. When Wertheimer appeared in Police Court, he was represented by a state senator; his $10,000 bail was posted by one Peter McGinnis, an East Side liquor dealer; and later that night a group of Tammany men went to the judge’s home to secure Wertheimer’s release. In New York City it paid to have friends in high places.

All the while that Roosevelt’s investigating committee met, his Aldermanic bill was making its way through the Assembly. The blatant example of corruption offered by the committee’s probe into the sheriff’s department, and the subsequent arrest of the undersheriff on February 1, provided an ideal backdrop for Roosevelt’s championing of the bill, which came up for a second reading in the Assembly on February 5. In what the Times referred to as an “excellent speech,” Roosevelt defended the bill by citing the low character of the aldermen and accusing them of being merely tools of the political machine. Moreover, aldermen were largely unknown and unelected, while any mayor, though perhaps equally as dishonest or corrupt, was at least a highly public figure and subject to being kicked out of office at the next election. Despite opposition from Democrats, the Roosevelt bill was ordered to a third reading and thus probable passage by the lower house. With a sense of triumph, Roosevelt wrote to his wife, Alice, of his victory in the Assembly, saying he had “made a nice strike in my speech on the aldermanic bill.”

The Roosevelt Committee hearings then took a dramatic turn when it was revealed that Mayor Franklin Edson and John Kelly had met before the election to discuss mayoral appointments. The city now enjoyed the spectacle of seeing both the mayor and the Tammany boss called before the Roosevelt Committee on February 9. In front of a packed parlor in the Metropolitan Hotel, Mayor Edson denied that any deals had been made—“No pledge or promise was made or suggested in regard to my appointments”—yet admitted to meeting at Kelly’s house with the men who would later receive appointments as fire commissioner and police commissioner. The committee then called John Kelly, who did a fair job of not answering the questions put to him. When asked if he had any objection to telling the committee about the meeting at his house, he replied, “I have an objection, and I don’t propose to tell it. The meeting was a private one, and this committee has no right to ask about it.” Yet he freely admitted meeting with the mayor and future department heads, as well as with aldermen, to discuss the mayor’s appointments. With no proof of any deals made other than the testimony of a disgruntled foe of the mayor, little came of Edson’s and Kelly’s testimony. For Roosevelt, though, the calling of Edson and Kelly had served its purpose: not to make their dealings the focus of his committee, but to expose them to the public as a way to garner support for his Aldermanic bill.

Despite Alice’s advanced pregnancy, Roosevelt returned to Albany on Tuesday, February 12, prepared to speak on behalf of his Aldermanic bill the following day. On Wednesday, he recorded out of the Cities Committee fourteen bills, and received a telegram reporting the birth of a baby girl. With the third reading of his bill imminent, Roosevelt requested a leave of absence from the Assembly as he received the congratulations of his fellow members. Before any debate on the bill could begin, Roosevelt received a second telegram from New York City. Both his wife and mother lay dying. The Aldermanic bill was laid aside and Roosevelt caught the next train for the city. The next day his mother, Mittie Bulloch Roosevelt, died of typhoid fever, and his wife, Alice, died of Bright’s disease, an inflammation of the kidneys that had been masked by the pregnancy. “On Feb. 12th 1884 her baby was born,” Roosevelt found the strength to write in his diary, “and on Feb. 14th she died in my arms, my mother had died in the same house, on the same day, but a few hours previously.” Their double funeral was held at the Fifth Avenue Presbyterian Church two days later. The next day, Roosevelt christened the baby Alice Lee. He took no joy in it, or in his newborn little girl—“her baby,” as he wrote. “For joy and for sorrow my life has now been lived out,” he lamented. He could not bear to call his daughter Alice, and instead referred to her as Baby Lee.

Four days after the funeral, Roosevelt was back in his seat in the Assembly, speaking on behalf of the Aldermanic bill. Roosevelt condemned “the aristocracy of the bad,” the men who fattened themselves in public office on money wrung from the workingman and the taxpayer. Despite vigorous politicking by Tammany representatives on the floor of the Assembly, the bill passed by a vote of 70 to 51, with 12 Democrats supporting the measure and 8 Republicans voting against it. Seven Assemblymen were absent that day, reported the Times, “afraid to vote against the bill because of the political pressure put upon them,” but also “afraid to take the opposite course because of the criticism which would follow them.” The bill now went to the Senate’s own Cities Committee.

Roosevelt’s investigating committee would reconvene only on February 23, and its record of hearings indicated nothing about Roosevelt’s tragedy. There was no call for a moment of silence or testimonials offered, as occurred in the Assembly in Albany. And while ink on a page does not easily reflect emotion, still, there appeared to be no change in Roosevelt’s tone or in the proceedings in general. One of Roosevelt’s favorite sayings was: “Black care rarely sits behind a rider whose pace is fast enough.” Roosevelt tried to turn his back on his grief, throwing himself into his work.

Returning its attention to the sheriff and the Ludlow Street Prison, the committee heard from James Bowe, the warden and brother of the previous sheriff. The committee noted that the warden charged the city 75 cents a day for each prisoner’s food, even though a large number of prisoners fed themselves. The warden was also asked about a bill for over $600 that the city paid, apparently to a furniture dealer for Brussels carpets ($175), a parlor suite ($150), a walnut table, and other items. The committee counsel asked, “Where did that furniture and bedding go?” “That is in my rooms,” the warden replied. New York’s taxpayers had outfitted Bowe’s rooms in a style befitting an Astor.

The testimony of a former deputy warden at the jail, Philip Kiernan, former keepers, and former prisoners attracted the attention of the committee and the press. Kiernan and others testified that a bar was operated out of one of the jail cells; the proceeds from the sale of beer and tobacco went to the sheriff. In fact, it was a common sight to see jail keepers drunk, and once on a Sunday the chaplain complained about the noise and profanity coming from the bar. The committee also heard testimony that rooms were rented to prisoners for the purpose of entertaining women. The prison was overcrowded, with three or even four prisoners in some cells, and the prisoners were covered with lice. There also seemed to be a custom of asking prisoners for a sort of exit tax of $1.50 when they were discharged. Kiernan testified about the bad food and putrid meat served to prisoners, and the bad language and violence directed at prisoners. Female visitors, it was noted, were not searched when they came into the jail, and thus could carry in contraband, and the tin buckets used to transport food to the prisoners were also used for cleaning the floors.

It was perhaps this testimony, and the attention it received in the press, that led to the committee taking the dramatic step of holding further hearings inside the jail itself. Legally this was required, as the committee had no authority to call prisoners before it to testify. The committee first heard from Augustine Ralph McDonald, the jail librarian, who had been a prisoner for five years. McDonald testified that there was a systematic effort to extort money from prisoners for better conditions. When McDonald was unable to pay this money, he had been sent to a cell with no warm water and next to a toilet, so that foul air would come through a hole in the wall. He had been told it was “all a question of money” whether he could get out of that cell, and the deputy warden had asked him for $250. McDonald explained the system of extortion and described the near-constant drunkenness of the keepers. He also testified about the bad food, with leftover meat trimmings bought from butchers to make soup. And he said that the warden had offered to carpet his cell if he did not testify—perhaps with a $175 Brussels carpet.

The prisoner’s litany of abuses continued. Some keepers continued to draw pay from the jail even after they had been discharged. The keepers supplied whiskey to, and borrowed money from, prisoners. Prisoners were allowed out of their cells as long as they had money to spend at the bar, and the revelry would continue late into the night. The sheriff, warden, and keepers would confiscate property and not return it. McDonald testified that when three keepers were discharged the previous May, they had three closets filled with furniture and other items taken from the prisoners’ cells. Prisoners were not given changes of clothing for months, and those responsible for serving food would be so filthy that the vermin on them would drop onto the food. When asked if he knew anything about women being brought in for the prisoners, McDonald replied, “Well, the place goes by the name of the sheriff’s whore-house.” Once when he heard there were “strumpets” in the cells alongside his, McDonald got very indignant and complained: “I was willing to be imprisoned anywhere, but not in a house of ill-fame, and that the State of New York had no authority to do that.” Nothing made headlines in New York like prostitutes serving prisoners.

Further testimony by other prisoners simply confirmed the stories the committee had already heard about drunkenness, extortion, theft, prostitution, bad language, filthy cells, and putrid food. Once again a city department had become the personal estate of a corrupt official, a situation allowed by Tammany’s control over the aldermen and by the aldermen’s power of confirmation of mayoral appointments. Once again the press covered the lurid tales of waste and corruption (“Abuses in Ludlow Street Jail Brought to Light,” one headline proclaimed). And once again the Roosevelt committee hearings paralleled the progress of the Roosevelt bill through the state legislature. The Senate passed the Aldermanic bill on March 5. It was “an important triumph for the cause of municipal reform in this city,” a Times editorial declared. All that was left now was for New York governor Grover Cleveland to sign the bill into law. The conclusion of the hearings of the investigating committee and its final report provided a perfect backdrop for the bill becoming law.

The committee adjourned only days before its final report was due on March 14. The report began with a sweeping statement that called the entire New York City government “absolutely appalling.” In the report, Roosevelt again took aim at the Board of Aldermen and the nefarious powers behind it: “Under the present system the men who nominally hold the offices are not the ones who really exercise the power, . . . [and such men] are generally outside the political parties, [and] cannot be held responsible to the people for their deeds and misdeeds.” The report then went through each department investigated and noted its findings. The clerk of the city of New York drew a salary of $3,000, but the current clerk had kept $13,700 in fees; his predecessor had kept $36,000. The register did not draw a salary and had only held his office since January 1, “but,” the report claimed, “it appears clearly from the evidence that if subsequent months pay him as well as the month of January did his net income for the year will amount to between $30,000 and $40,000.” The sheriff was being paid massive compensation for services that cost him very little, such as for transportation, food, and even hangings. But it was the committee’s investigation of the Ludlow Street Jail that uncovered, in the report’s words, “a most revolting and almost incredible state of affairs,” where drunken and brutal keepers operated a system of extortion and blackmail. The sheriff, one of the city’s top law enforcement officials, was in reality the ringleader of a massive scam involving the deputies and keepers at the jail.

Roosevelt followed submission of the report with the introduction of nine bills mainly having to do with reforming the system of fee collection in the various offices, which he claimed could save the city $200,000 a year. But the bills also included one to change the office of controller from an appointed to an elective office, and a bill to elect a president of the Board of Aldermen to preside over all aldermanic meetings. Most of these bills were eventually made into law, but none was as important as Roosevelt’s Aldermanic bill, which Governor Cleveland signed into law on March 17, only a few days after the investigating committee submitted its report. Through his bill, Roosevelt sought to make the office of mayor more powerful by creating a strong executive who was directly responsible to the people. Whether for city mayor, state governor, or president of the United States, enhancement of executive power would be a hallmark of Roosevelt’s political thought.

ROOSEVELT’S ALDERMANIC BILL and his investigative committee altered the way America’s largest city was governed. For years to come, Roosevelt would refer to his intimate knowledge of New York politics. In 1886, for Century magazine, Roosevelt wrote an article on “Machine Politics in New York City,” in which he recounted some of the committee’s findings, including the large amounts of money that found their way through the city department heads to the political organizations. “The enormous emoluments of such officers are, of course, most effective in debauching politics,” he wrote. “They bear no relation whatever to the trifling quantity of work done, and the chosen candidate readily recognizes what is the exact truth—namely, that the benefit of his service is expected to enure [hand over] to his party allies, and not to the citizens at large.” In his 1891 history of New York, Roosevelt referred to machine politicians as “a solid, well-disciplined army of evil.” And the value of the committee hearings to Roosevelt’s career cannot be underestimated. In facing Senate opposition, press skepticism, and Tammany obstructionism, Roosevelt had faced down dogged opponents. He had secured an education in the intricacies of city government, from the clerk’s office to the city prison. Roosevelt had also been exposed to a hierarchy of heelers and hacks, from men like Hubert Thompson, whom Roosevelt had first espied wearing his diamond stickpin in Albany, all the way to the mayor’s office. Roosevelt had learned the power of the press in pursuing his legislative agenda, and how to pursue reform within the framework of the party. He had even worked with Democrats, securing their votes in the Assembly and securing Governor Cleveland’s signature. Roosevelt had also affected real change in the way America’s largest city was governed by enhancing the executive power of the mayor.

Roosevelt had proven himself a skilled and tough politician at age twenty-five. But with his double tragedy, any future political career was left very much in doubt. He would soon flee the city for his Dakota ranch, which he had purchased only the year before. Yet family, friends, and politics would constantly work to draw Roosevelt back home.