When he was a young, prickly, state senator from the Hudson Valley, Franklin Delano Roosevelt made little secret about his distaste for his fellow Democrats from New York City. He was particularly disdainful of the city's most-powerful Democrat, Charles Francis Murphy, the boss of Tammany Hall.
"C.F. Murphy and his kind must, like the noxious weed, be plucked out," Roosevelt wrote.
"From the ruins of the political machines we will construct something more nearly conforming to a democratic conception of government."
A funny thing happened - to Murphy, to Tammany, and to Roosevelt - on the road to ruin.
Murphy gained enormous respect, even from traditional foes of machine politics, for putting Tammany on the side of social reform. Tammany went on to produce two of New York's greatest political figures, Alfred E. Smith and Robert F. Wagner.
And Roosevelt made his peace with Murphy and Tammany, realizing that they were on the right side of
And so it came to pass that on Franklin Roosevelt's final and most-controversial diplomatic mission - the Yalta Conference, in 1945 - a protégé of Charles Francis Murphy was by his side, an important player in one of the most-important conferences of the 20th Century.
The Murphy protégé was Edward J. Flynn, the son of Irish immigrants and Democratic boss of the Bronx.
Well-educated, sophisticated, and politically savvy, Flynn was FDR's most-important political advisor after Louis Howe, the onetime newspaper reporter who died in 1936 after engineering Roosevelt's rise to the top.
Flynn was with Roosevelt when FDR was Governor of New York, and while he declined job offers from the White House during the New Deal years, he was in constant touch with the president throughout his tenure.
Ed Flynn probably would qualify as the nation's most-underrated political boss, mainly because he preferred it that way. He was not outgoing like Al Smith, he was not a backslapper like James A. Farley, who ran the Democratic National Committee for FDR in the 1930s. And unlike bosses
like Frank Hague of Jersey City, James Michael Curley in Boston, and Jim Pendergast in Kansas City, Flynn did not aspire to elective office.
He preferred, instead, to operate behind the scenes, and became one of the 20th Century's most-effective political bosses.
He ruled the Bronx from 1922, when Charles Murphy asked him to take charge of the borough, until his death some three decades later. He was instrumental in winning Irish-American support for FDR at the 1932 Democratic National Convention, when Al Smith challenged Roosevelt for the party's presidential nomination. And he helped choose Roosevelt's successor at the 1944 convention when he and a handful of other Irish-American bosses insisted on nominating Harry Truman for vice president, rather than the incumbent VP, Henry Wallace.
Flynn's long career as a political operative, a patronage dispenser, a fixer, and a power broker was remarkably free of scandal, save for an incident which now seems quaint.
In the early 1940s, city workers were dispatched to Flynn's upstate vacation home to build a new driveway. Flynn was traveling at the time and apparently knew nothing of the city workers' involvement in the job. He repaid the city for the material (about $80) and for the labor (less than $800).
Nevertheless, when Roosevelt nominated Flynn to be a U.S. envoy to Australia in 1943, Republicans in Congress and anti-Roosevelt voters assailed the nomination as a dirty political deal.
One critic referred to Flynn as a "Tammany grafter." Other letters pouring into the White House charged that Flynn was not worthy to be a diplomat because he was a corrupt Tammany politician. Flynn, no doubt stunned by the outrage, withdrew his name.
The outpouring of vitriol against Flynn illustrated that even in 1943, years after Al Smith's failed presidential campaign of 1928, many in the American heartland retained their traditional bias against Catholics, the Irish, and cities.
The anti-Flynn letters, many of which are collected in Flynn's correspondence in the FDR Library in Hyde Park, equated Flynn with corruption simply because he was an Irish-Catholic from a city. It didn't matter to his critics that Flynn was not a member of Tammany Hall (as a resident of the Bronx, he was ineligible for membership) and had actually turned against the Hall in the 1930s.
Unfortunately, FDR did not put up a fight on Flynn's behalf, but the two men remained close.
Flynn and his wife, Helen, were frequent visitors to Hyde Park and the White House, and FDR felt obliged to write Helen Flynn a letter in 1940, apologizing for monopolizing her husband's time during that year's presidential campaign.
Eleanor Roosevelt occasionally dropped Flynn letters about friends of hers who were looking for jobs in the public or private sector. Flynn found himself in a quandary in 1941 when the First Lady wrote him on behalf of a friend who wanted a patronage job in Portland, Oregon.
When Flynn was unresponsive, Mrs. Roosevelt enlisted her husband, the president, to lobby Flynn. The boss decided to attack the issue head-on. Referring to Mrs. Roosevelt's friend, Flynn wrote: "She has been a constant source of irritation to the local Democratic Organization."
Mrs. Roosevelt's friend did not get the job.
Ed Flynn was one brave boss. Despite his adamant refusal to find a job for the First Lady's friend, Flynn and Eleanor Roosevelt enjoyed a remarkable relationship as well - remarkable, in part, because Eleanor Roosevelt was from an anti-machine reform tradition, even more so than her husband. And Flynn was an unapologetic boss, a creature of, and believer in, machine politics. They were an odd couple, but Mrs. Roosevelt gladly wrote an introduction to Flynn's entertaining memoir, "You're the Boss," published in the late 1940s.
These two very different people shared a belief in the New Deal policies and politics of the Roosevelt administration, and a shared world view that the second half of the 20th Century required justice for oppressed people around the world. Flynn enunciated that view in a letter to
Mrs. Roosevelt in 1943, as World War II was raging.
"On reading your column today," Flynn wrote to Mrs. Roosevelt, who wrote a syndicated newspaper column while serving as First Lady, "I noticed that you emphasize the lack of understanding that the Anglo-Saxon has for the membership of both the brown and colored races of people. It seems to me that we can never have a complete settlement of world conditions until the Anglo-Saxon begins to realize that he is not of a superior race but that all races are equal."
Flynn continued: "Certainly, we are today fighting against the ideology of Hitler in which he sets forth the Aryans as superior people to all others. We do not seem to be consistent when we fight against this doctrine and on the other hand do nothing to try to bring about a better understanding" between the races."
While Flynn's predecessor as chairman of the Democratic National Committee, James Farley, felt that FDR treated him like household help - Farley noted with some bitterness that he was never invited to dinner at the White House - Flynn clearly enjoyed a close personal rapport with the president and his wife.
Flynn received the invitations which were denied Farley. No doubt snobbery was part of the equation. Flynn, the son of a doctor and a graduate of Fordham Law School, was better-educated, better-read, and far more worldly than Farley and many other Irish-American politicians at the time. FDR, the squire from the Hudson Valley, likely felt more at home with Flynn than he did with Farley and other clubhouse pols.
That relationship led to FDR to send Flynn to the Soviet Union after the Yalta conference to report on the state of religious organizations in that communist nation.
Josef Stalin approved the secret mission, and Flynn flew to Moscow to gather intelligence. He met with Pope Pius XII afterwards to talk about church issues in the post-war world. Flynn was out of the country when his friend and boss, Franklin Roosevelt, died in Warm Springs in April, 1945.
Flynn continued to play an important role in national politics through the Truman administration. But it was his relationship with Roosevelt which defined Flynn's career.
The protégé of Charles Francis Murphy, the greatest boss in Tammany's history, rose to become one of the most important advisors to the most important American president of the 20th Century.
The story of Flynn and Roosevelt shows that would-be reformers like FDR came to appreciate the pragmatism of Irish-American bosses who produced tangible results, and who firmly believed in the power of government to effect change.