“In With Flynn”: Why I Wrote the Book & How Political Levers Have Changed Since FDR

January 21, 2021 Malcolm MacKay, Author

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Party organizations — particularly the big city machines — used to own the field. They made a simple offer to voters, particularly unskilled immigrants and their offspring: Give us your votes and we will find you patronage jobs, other assistance, and even elective opportunities. The politically ambitious could work their way up the organization’s ladder — Al Smith, Robert Wagner Sr. and Harry Truman all did.

While the machines mastered vote gathering, they often failed at governance. Dishonesty and self-dealing were coins of the realm. Mention Tammany Hall or Boss Tweed and I’ll bet your first thought is corruption. As a British ambassador once put it: “There is no denying that the government of the cities is the one conspicuous failure of the United States.”

Times have changed. Today the levers of political power are money, celebrity, television, social media. Donald Trump was able to take over the Republican Party because it was so weak. So is the decline of party power progress? Maybe, but I have my doubts. It has gone too far. Listen to Professor Sean Wilentz of Princeton: “A lot of people just don’t like political parties, and I think that is a terrible thing. Political parties are how we get things done…in American politics. And the more we weaken them, the less gets done.”

I thought it would be interesting to search for an example of a good machine run by an honest, competent, public-spirited boss. The search was a short one, at least geographically, as it ended just across the Harlem River in the Bronx. The winning boss: Edward J. Flynn, chairman of the Bronx Democratic Party from 1922 until his death in 1953.

Initially, I assumed that Flynn’s story would take place entirely within the borders of the Bronx. I had no idea of his close personal relationship with FDR and his significant national role during the Roosevelt and Truman years. I also discovered several things that a potential biographer would appreciate. No one had written a biography of Flynn. His papers, including correspondence with Franklin and Eleanor Roosevelt, Harry Truman, Hubert Humphrey, and many others, are maintained at the Roosevelt Presidential Library at Hyde Park. There is an oral history at Columbia. A few of the most insightful reporters of the time, including Warren Moscow at the Times and Richard Rovere at The New Yorker, were on to Flynn’s importance. In recent decades, historians and memoirists have given Flynn significant attention. All this public exposure came despite Flynn’s conscious effort to stay backstage. He once advised Carmine DeSapio, the Tammany (or Manhattan) leader, to avoid the press because people don’t like what bosses do. His advice was ignored and DeSapio ended his career in prison.

The biggest and best surprise I had in uncovering the Flynn story was the discovery of his three children (one of whom has since died). They introduced me to their father’s warmth, humor, and personal values. He encouraged his children to be inclusive and to oppose all forms of racial or religious discrimination. He railed to the family against the Red scare promoters culminating in Joe McCarthy. He was well-read — particularly history and biography — and encouraged his children to be the same. The children had many stories including of weekends spent at the White House. They believe, incidentally, that trips to the White House had less to do with their father’s close friendship with FDR and more with the president’s desire to flirt with their mother.

The Flynn children were helpful in another way. We sat together at kitchen tables going through boxes of old photographs, letters, and articles. Several of these photographs are in the book including one of FDR and Flynn astride horses with the president’s leg brace appearing below his pants cuff. Of course, knowing and liking the Flynn children add to a biographer’s occupational hazard: getting to like one’s subject so much that you lose objectivity.

Flynn’s parents came directly from Ireland to Mott Haven in the South Bronx in 1870. The borough was largely farmland with a population of 37,400. Mrs. Flynn, recognizing the area’s potential for residential development, saved every penny she could and bought small properties. When the Third Avenue El and the subway crossed the Harlem River from Manhattan in 1888 and 1904 respectively, land values soared. According to The New Yorker: “ Lots leaped from five hundred dollars to five thousand dollars literally overnight.” By 1930, the population had grown to 1.3 million, making the Bronx, standing alone, the eighth-largest city in the country.

Ed Flynn was the youngest of five children. The family, thanks to Mrs. Flynn, was relatively prosperous, certainly by Mott Haven standards. One brother became a beloved local doctor, a sister became a school principal, and another married George Meaney, who became head of the AFL-CIO. Ed, skipping college, graduated from Fordham law school at age 20 and was elected to the state assembly at age 25. Five years later he became party boss.

The Bronx Democratic Party was the most successful urban political machine in the country. Flynn exercised virtually complete control, with the party never losing an election. Personally honest and able, his handpicked candidates and patronage appointees — particularly at the higher-level positions such as borough president and district attorney — were known for being the same. It was said that, when members of the Mafia wanted to go from Westchester to Manhattan, they traveled via New Jersey to avoid arrest. According to historian Allen Nevins: “Flynn gave the Bronx a reputation for political independence, intelligence, and integrity. It was “the good borough,” even “a capital of civilized thought.”

For 30 years, while always the boss of the Bronx, Flynn played an important role on the national stage: He convinced a reluctant FDR to run for governor in 1928; he was crucial in Roosevelt’s winning the Democratic presidential nomination over Al Smith on the third ballot in 1932; as New York secretary of state for twelve years under governors Roosevelt and Lehman, and as regional administrator of the National Recovery Administration, he was the state’s chief patronage dispenser and responsible for directing huge amounts of New Deal spending to the New York region; he ran FDR’s 1940 campaign and served as chairman of the national Democratic party for several years following; his advice caused Roosevelt to drop Vice President Henry Wallace from the ticket in 1944, and he then literally chose Harry Truman to replace Wallace. His family has a photograph Truman sent to Flynn after becoming President with the inscription: “My very best to my friend Ed Flynn who helped me run into a lot of trouble.” Flynn knew by the spring of 1944 that FDR was very ill, and was the one person close to him that tried — and tried hard — to convince him not to run for a fourth term; nevertheless, all the correspondence involving Truman’s selection focuses on electability and not presidential qualifications.

My book focuses on several personal relationships Flynn had, although as he himself noted, it could be hard to separate the personal from the political. The first was with Charles Francis Murphy, the bar owner and Tammany leader from 1902 until his death in 1924. Murphy and Flynn had a father-son relationship that led to Flynn becoming boss and initially maintaining his position as a result of the Bronx receiving attractive patronage. Murphy was a fascinating character with an upright reputation: no profanity or women in his bars, no bribes to police or other government officials from gambling and prostitution interests. And yet he died a rich man with hidden ownership in companies that benefited from his political influence. Some might call it “honest graft.”

Another Flynn relationship — already mentioned — was with Al Smith, in 1928 the first Catholic major-party presidential candidate. Flynn, eighteen years younger, adored — and identified with — Smith and worked closely with him in the 1920s. Their relationship ended abruptly in a shouting match in a Chicago hotel room at the 1932 Democratic convention when Flynn refused to abandon Roosevelt in favor of Smith. Flynn described his break with Smith as “one of the saddest experiences I have ever had.”

Flynn and FDR, nine years senior, began both a social and political friendship after working together for Smith at the 1924 Democratic convention. After Roosevelt went on to the White House, he made several attempts to recruit Flynn to join the administration. One was to get Governor Lehman to appoint Flynn to fill a US Senate vacancy, an idea that failed when Al Smith refused to give his approval. Roosevelt also offered Flynn the ambassadorship to Germany in 1933, the year Hitler consolidated his power, but Flynn turned it down. During the 1930’s Flynn was often at the White House, and — as already mentioned — ran the 1940 campaign and the entire party for two years after. In 1943 Roosevelt nominated Flynn to be ambassador to Australia, but Flynn, for a complicated set of reasons discussed in the book, withdrew from consideration after being approved by the Senate foreign relations committee. Late in the war, Roosevelt asked Flynn to undertake a month-long fact finding mission to the Soviet Union. When FDR, shortly before his death, attended the Yalta conference on the post-war world with Stalin and Churchill, he insisted Flynn accompany him.

Flynn had no foreign policy credentials. Nevertheless, Roosevelt thought he would be a good diplomat. Maybe the second secretary in the U.S. embassy in Moscow, who accompanied Flynn on his Soviet mission, caught why: “For me, the association with Edward Flynn was pure delight. The public image of a Tammany type of political boss had nothing to do with Ed Flynn. Urbane, worldly, beautifully and comprehensively educated, humorous, a world traveler, he had all the charm and magnetism in the world.”

Roosevelt also knew that he got the truth from Flynn, who was known around the White House for his directness and honesty. To mention two examples, Flynn argued strenuously but vainly against FDR’s court-packing effort and his attempt to purge “yes but” Democrats in primaries in 1938. Despite Flynn’s advice not always being followed, Bernard Baruch, the financier, and New Deal insider could write in his memoir: “While everyone professed a willingness to do what the boss — Roosevelt — wanted, the boss did what Ed Flynn wanted.”

Did Roosevelt and Flynn have a genuine friendship? It is true that they came from different worlds. Al Smith, Jim Farley, and Joe Kennedy, all Irish Catholics, complained about how Roosevelt never accepted them as social friends. Eleanor Roosevelt once said: “Franklin finds it hard to relax with people who are not his social equals.” There are some who questioned whether Roosevelt had personal friends. Arthur Schlesinger Jr. described the president as “…glittering, impersonal…superficially warm, basically cold.” His longtime secretary and companion, Missy LeHand, believed he “…was really incapable of personal friendship with anyone.”

Flynn, although he could be critical of Roosevelt, clearly considered the president to be a close friend. He wrote of his feelings upon learning of FDR’s death: “For our friendship through the years had come to be very deep and affectionate. Incidents, small in themselves, but magnified by their multitude, stood out one by one in high relief.” Although Flynn might occasionally joke about Roosevelt’s old school friends who cruised with him aboard Vincent Astor’s yacht on the Potomac, he seems never to have sensed or experienced any condescension or snobbery toward him by the president.

A final Flynn friendship — with Eleanor Roosevelt — deserves mention. Both Helen and Ed Flynn adored Eleanor, and Flynn’s daughter remembers that, after FDR’s death, Mrs. Roosevelt was often a guest in both the Bronx and at Flynn’s country place. Eleanor and Flynn were allied in promoting civil rights, various federal programs, and recognition of Israel. Interestingly, however, Flynn saw Eleanor during her marriage as a less powerful influence on her husband than did many others. He wrote: “I believe from my intimate observations covering a long period of years that Mrs. Roosevelt was credited with more influence than she actually had.”

In 1949, Cardinal Spellman of New York attacked Eleanor Roosevelt repeatedly for being, among other things, a bad mother and soft on communism. Eleanor, a strong supporter of federal funding of public schools, had refused to advocate extending such support to parochial schools. Flynn publically defended Mrs. Roosevelt, and secretly flew to Rome, met with Pope Pius XII , and got the Pope to call Spellman off. When Flynn died four years later, his large funeral in the old Mott Haven neighborhood involved a crowded church and two thousand attendees outside on the streets. Many notable Washington and New York figures were there, and it was an upper left front page end story in the Times. There was one notable and noticed absentee: Cardinal Spellman.

Let me close with a quote from a memoir by Eleanor Roosevelt: “Ed Flynn was more of an intellectual than the usual run-of-the-mill city boss. Perhaps that is why he understood the aims and objectives of the New Deal so well and why he made it his business to really understand and study my husband as a human being and as a politician and a statesman. He forgave that as a politician my husband really let him down. Actually, he was much more forgiving and understanding than I often was because I was a less good politician, and Ed Flynn could see beyond the actions of the moment to the ultimate ends…”

Ed Flynn was a moral man in a practical world. Noted theologian Reinhold Niebuhr caught the connection between politics and purpose when he wrote: “The moral achievement of statesmen must be judged in terms which take account of the limitations of human society which the statesman must, and the prophet need not, consider.”