Franklin Roosevelt Takes on Tammany Hall

Editor's Note: Michael Wolraich is a journalist and author based in New York City. The following was adapted and condensed from his recent book, The Bishop and the Butterfly: Murder, Politics, and the End of the Jazz Age.

In the summer of 1932, Franklin Delano Roosevelt, then governor of New York, faced a dilemma. His presidential ambitions depended on a precarious alliance with Tammany Hall, the political machine that ruled New York City. Though eager to separate himself from the corrupt Tammany bosses, he needed their support to win his home state, the largest in the nation.

Two years earlier, he’d made a show of independence by initiating a limited state investigation into allegations of bribery by city officials. But the man he chose to lead the investigation, an imperious former judge named Samuel Seabury, uncovered something more sinister—a conspiracy to frame innocent women for prostitution. After one of Seabury’s witnesses, Vivian Gordon, was murdered, outraged New Yorkers demanded a full investigation of Tammany Hall.

Bowing to the political pressure, FDR reluctantly expanded Samuel Seabury’s authority. With his new powers, the tenacious investigator pursued the trail of graft up the political hierarchy, ultimately uncovering a million-dollar slush fund controlled by New York City’s flamboyant, wise-cracking mayor, Jimmy Walker.

Seabury’s stunning allegations magnified Roosevelt’s predicament. As governor, he had the authority to remove Walker for corruption, but deposing the popular mayor would infuriate Tammany’s bosses. He deferred his decision until after the Democratic national convention in Chicago, which allowed him to secure enough Tammany delegates to win the presidential nomination. But, when he returned to Albany, he could no longer avoid the predicament.

Over the next few weeks, Roosevelt received a flood of entreaties and unsolicited advice about the Walker problem. Some warned that, if he removed the mayor, he would certainly lose New York and likely Massachusetts, New Jersey, Illinois, and Connecticut. Others insisted that, if he didn’t remove Walker, he’d lose independents and progressive Republicans, which could jeopardize the western states. Roosevelt’s campaign manager, Jim Farley, who counted Walker as a personal friend, also urged FDR to spare the mayor.

In response to these conflicting appeals, Roosevelt vacillated. “On one occasion while talking over the subject,” his adviser, Raymond Moley, recalled, “Roosevelt said, half to me and half to himself, ‘How would it be if I let the little mayor off with a hell of a reprimand?’ Then suddenly, as if answering himself, Roosevelt said sharply, ‘No. That would be weak.’”

A month after the convention, he summoned Mayor Walker and Judge Seabury to appear before him at a special hearing in the capitol in Albany. Reporters noted that the first hearing would overshadow Herbert Hoover’s acceptance speech as the Republican nominee, which was scheduled for the same day. 

“By George! That is the day, isn’t it?” Roosevelt innocently replied. “I want you all to know that there is absolutely no connection with the Walker case and my campaign for the presidency.”

Both parties assembled in the Executive Chamber of the capitol on August 11, 1932, Seabury and his assistants sat at a long table to the right of the governor’s great mahogany desk. Walker sat with two attorneys at a table on the left. A waist-high brass rail, borrowed from the Assembly Chamber, separated 60 reporters and roughly the same number of spectators at the back of the room. Portraits of governors past gazed down upon the proceedings as sunlight filtered through stained-glass windows. 

At 1:40 p.m., the door to the governor’s private office opened, and the room hushed. Roosevelt stood in the doorway, looking about the chamber with his chin in the air. Then, with his secretary gripping one arm, he began to stagger across the red carpet. Only the thump of his feet and the creak of his braces broke the silence as he labored over to the desk and dropped wearily into the high-backed leather chair.

The governor’s hearings focused on the same topics that Seabury had addressed during Walker’s previous appearance at the County Courthouse, but the setting was completely different. Gone were the mayor’s crowd-pleasing witticisms, the rowdy spectators, and the disruptive committee members. Walker’s lead attorney, John Curtin, was a truculent Tammany loyalist, but Roosevelt rebuffed his attempts to call witnesses who hadn’t previously testified. 

The governor made clear that he would be the judge and jury, and he brooked no attempt to obstruct or derail the proceedings, repeatedly reminding Walker and Curtin to stick to the evidence. When Walker compared the hearings to Soviet tribunals and medieval trials, Roosevelt patiently assured him that he would be given a “square deal.” When Curtin presumed to lecture him about the law, Roosevelt retorted, “Mr. Curtin, I happen to be a lawyer, and remarks of that kind are wholly unnecessary to the governor of this state.” 

For the next two weeks, Roosevelt methodically led Mayor Walker through Judge Seabury’s accusations, interjecting incisive questions when the mayor gave evasive answers. After Walker declared that he hadn’t even looked at the $26,500 in bonds that he’d received from investment banker J. A. Sisto, Roosevelt asked, “How many shares did you think you were getting?” 

“I beg your pardon?” Walker replied.

“How many shares?”

“I don’t know that . . . ,” Walker stammered, “if I did know . . . but I...my understanding was...In view...there were no questions about it . . . In fact, if I never heard of it again, it would been all right with me. . .  I wouldn’t have probably complained about it. I mean, there was no definite agreement about it.”

Roosevelt also grilled the various businessmen who had been so generous to the mayor. As Samuel Ungerleider tried to explain the complex arrangement whereby Russell Sherwood, as Walker’s agent, was permitted to earn profits from a stock-market investment without risking any capital or even paying taxes, Roosevelt shook his head in disbelief. “Most extraordinary business proposition I ever heard of!” he scoffed. “How was it you conferred this valuable privilege on Mr. Sherwood when thousands of other people in every state in the Union didn’t get it?”

Later, when questioning the mayor about Sherwood’s disappearing act, Roosevelt expressed incredulity that Walker hadn’t tried to contact him. “Isn’t it a curious thing for you,” he asked, “when a man with whom you had a safe-deposit box, and who looked after your personal affairs, disappears, and the whole town is looking for him, and he turns up, not to communicate with him?”

Walker responded with a series of evasions, denying that he knew Russell Sherwood well, that the “whole town” was looking for him, or that he had a way to reach him—even though Sherwood’s hotel had been reported by every newspaper in the city. 

As the mayor continued to hedge, Roosevelt crossly exclaimed, “So, you just let it ride?” 

“Well, now, your Excellency may characterize it as you will,” Walker answered, taken aback. “I would so much rather he were here today.” 

“I wish he were here,” the governor rejoined.

The hearings weren’t going well, and Walker knew it. Any hope that he harbored of leniency from the governor was dashed when Tammany district leader John Ahearn came to his hotel one evening to warn him that Roosevelt had already decided to remove him. 

“I don’t know why he’d make up his mind to do that,” Walker responded. “Who told you he would?” 

Ahearn said that he couldn’t reveal his source, but vouched for his dependability. He advised Walker to resign and run for governor himself to seek vindication from the voters.

When the hearings adjourned for the weekend on August 26, Walker returned to New York City. The next day, he received more unhappy news from another quarter: his younger brother, George, had died of tuberculosis. The hearings were delayed for a week, and the mayor kept to his bed until the funeral on September 1. At the cemetery, he had another conversation on the topic with his sister, Nan. “Sis, take a short stroll with me,” he said. “I’ve got something to tell you.” He led her over to the gravesite of former Tammany boss Charles Murphy and reflected silently for a few moments before the tombstone. “Mr. Murphy once told me that most of the troubles of the world could be avoided if men opened their minds instead of their mouths,” he said to Nan. “I’m going to resign.” 

“When, Jim?” she asked, shocked.

“Now,” he said, “Or as soon as I leave the meeting at the Plaza.” 

Eighteen Tammany leaders met him the Plaza Hotel that afternoon, including Boss Curry and Al Smith. “We sat at a round table, Smith at my left,” Walker later recalled in an interview. “One by one, the boys rose to say to me, ‘Jim—stick! Let that man toss you out. We’ll nominate you again, and the people will send you back to City Hall.’” Seventeen of the participants encouraged him to fight the charges. Only Smith remained silent. “What does my friend Al say?” Walker finally asked. 

“Smith rose and looked directly across the table, without even facing me,” he continued. “Speaking out of the corner of his mouth, he snarled, ‘You’re through. The public don’t want you. If you’re nominated, you’ll be licked. You’re through.’” 

That evening, several of Roosevelt’s advisers, including Jim Farley, came to see the governor at the Executive Mansion. At the stormy meeting, the visitors emphatically urged him to spare the mayor. Toward the end of the conference, Basil O’Connor, a member of the brain trust, lit a cigarette and hurled the spent match in Roosevelt’s direction. “So, you’d rather be right than president?” he snapped. 

“Well, there may be something in what you say,” Roosevelt calmly replied. 

At that moment, the telephone rang. There was news. Jimmy Walker had sent a message to the city clerk: “I hereby resign as mayor of the City of New York, the same to take effect immediately.”

The mayor’s resignation put an end to the inquiry led by Samuel Seabury. Only a few journalists and visitors were present the next day when Governor Roosevelt lowered himself into his high-backed chair in the Executive Chamber and addressed the room: “The Honorable James J. Walker has resigned his office as mayor of the City of New York,” he declared. “His action in doing so has terminated the proceedings before me, as governor of this state, and I, therefore, declare the hearing closed.”