Edward J. Flynn

Edward J. Flynn was a Democratic political boss whose influence reached the White House and whose intervention helped make Harry S. Truman Franklin D. Roosevelt’s 1944 running mate. His importance lay not simply in backing Truman, but in identifying the political risks Roosevelt’s party faced, pressing the President to consider an alternative to Henry Wallace, and then helping turn that preference into a convention victory. For a time, the decisive work happened in private meetings and phone calls; its consequences became visible in the delegates’ shifting votes in Chicago.

A Political Organizer Close to Roosevelt

Since the downfall of Tom Pendergast, Flynn was regarded as the country’s most powerful political boss. The book presents him as an unlikely-looking embodiment of that power: at fifty-two, he was tall and handsome, with thinning gray hair and gray eyes, dressed beautifully, well educated, devoted to gardening, and a student of history. His cultivation distinguished him from the familiar caricature of a successful Irish politician, but his access to Roosevelt was the more consequential fact. Flynn was a devoted friend of the President, and his influence on Roosevelt’s political decisions was described as greater than that of anyone else inside or outside the administration.

Flynn had already demonstrated his value in presidential politics by running Roosevelt’s successful 1940 bid for a third term. In 1944, he again approached the election as an organizer confronting a practical problem: the incumbent’s victory was not assured, and the choice of a running mate could affect the party’s prospects. After Roosevelt asked him to survey opinion across the country, Flynn reported that opposition to Wallace was stronger than expected. He warned that Wallace might cost Roosevelt New York, Pennsylvania, New Jersey, and California—a prediction the account identifies as exaggerated, but which conveyed the stakes Flynn believed the party faced.

Assessing the Alternatives

Flynn and Roosevelt reviewed possible candidates together, weighing their political liabilities as well as their strengths. James Byrnes appeared to be the strongest alternative, but Flynn considered his record a serious obstacle. Byrnes had left the Catholic Church after marrying and, in Flynn’s view, Catholics would not accept him. Organized labor was also cool toward Byrnes because he had opposed wartime sit-down strikes. Most damaging to Flynn’s calculations, Byrnes was a southerner with a record of opposing civil-rights measures, including a prominent fight against a proposed federal anti-lynching law. Flynn’s analysis therefore joined electoral arithmetic to the party’s divisions over race and labor.

Sam Rayburn was a good candidate in Flynn and Roosevelt’s assessment, but his Texas background made him another southern choice. As Flynn later described the review of the Senate, only Truman fitted the picture: his work as head of the Senate committee was excellent, his labor votes were good, he came from a border state, and he had made no racial remarks. Flynn summarized the apparent fit with the words, “He just dropped into the slot.” This was not an enthusiastic claim that Truman was the most inspiring candidate. It was an argument that he could hold together constituencies that might reject Wallace or Byrnes.

Flynn left the White House convinced Roosevelt had agreed that Truman was the safest alternative. The account cautions that Roosevelt’s manner could leave others with the impression they wanted, and that Flynn’s confidence was not the same as an unambiguous presidential endorsement. The distinction mattered: the choice remained unsettled, and Byrnes still had powerful support. But Flynn had secured what he needed to continue pressing the case in Chicago.

Turning Preference into Convention Votes

When Flynn arrived in Chicago on June 18, 1944, Bob Hannegan told him that the contest was over and Byrnes had been chosen. Flynn rejected that conclusion and demanded that the select committee meet again in its secret North Side apartment, this time with Sidney Hillman present and Byrnes absent. He insisted that Truman was the candidate they had agreed upon with Roosevelt. Flynn later recalled, “I browbeat the committee, I talked, I argued, I swore.” Hillman declared Byrnes unacceptable to organized labor; Flynn argued that Byrnes could cost 200,000 Black votes in New York alone. The group—including Hannegan, Ed Pauley, Frank Walker, George E. Allen, Hillman, and Edward J. Kelly—came around to the argument that Byrnes was a political liability and could endanger Roosevelt’s reelection.

Flynn then called Roosevelt in San Diego and passed the phone among the men in the room. Roosevelt ultimately agreed that Truman should be the choice. The account notes uncertainty about the subsequent details: Truman heard the decision from Hannegan, who showed him a handwritten note attributed to Roosevelt, but Truman doubted whether the note represented the President’s intent. Flynn’s success was consequently political rather than ceremonial; he helped produce agreement among party leaders without removing the ambiguity surrounding Roosevelt’s own wishes.

At the convention, Flynn and the other Truman supporters worked through the night, speaking with delegates and applying pressure. The strategy was to arrange as many favorite-son nominations as possible so Wallace could not win on the first ballot. Sixteen vice-presidential nominations resulted. The first ballot gave Wallace 429 votes and Truman 319, confirming that Wallace had substantial support despite the organized effort against him. When the convention unexpectedly proceeded to a second ballot during the afternoon session, Flynn delivered 74 New York votes to Truman. Alabama’s favorite-son candidate then withdrew and transferred 22 votes to Truman; other delegations followed, and the movement gathered force. Flynn’s delivery of New York’s votes was not the whole victory, but it was the pivotal shift that moved Truman into the lead.

Political Significance and Later Recognition

Wallace accepted the defeat without bitterness and gave the ticket his support. In retrospect, the book emphasizes how little the convention’s public account revealed about Flynn’s role. He had persuaded Roosevelt that Wallace threatened the ticket, resisted the assumption that Byrnes was already settled, and timed the transfer of New York’s delegation to the second ballot. Bernard Baruch later captured the reversal of influence by saying that although everyone professed willingness to do what Roosevelt wanted, “the Boss did what Ed Flynn wanted.”

Flynn’s intervention illustrates the force—and limits—of political organization in choosing a vice-presidential nominee. He could survey opinion, frame risks, persuade party leaders, and move a major delegation, but the outcome still depended on Roosevelt’s assent and the convention’s changing votes. Nor did Flynn’s argument rest on a single faction: it connected labor’s objections to Byrnes, concern about Black voters, and conservative Democrats’ greater comfort with Truman. The result was a choice built through negotiation and electoral calculation, with Flynn emerging as the central broker behind Truman’s nomination.