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Political Boss

June 2024
4min read

Most Overrated Political Boss:

William Magear Tweed, the man so connected with the American urban machine that he alone bears the title “Boss.” Overrated? Sure. After all, how shrewd and powerful could he have been? First of all, he couldn’t get himself elected as New York’s sheriff in 1861. Secondly, not long after he took control of New York’s political machine, he got caught, went to prison, and died in disgrace. Many bosses who were more corrupt managed to avoid such a harsh fate, perhaps because, unlike Tweed, they made sure they controlled the prosecutors and the newspaper editors.

Tweed’s name, of course, is intimately associated with that of Tammany Hall. But Tweed did not invent t the intimate social club that became America’s most famous political club-house, as so many peo- ^ pie seem to believe. Tarn- many was founded in 1789, and long before Tweed’s time the organization was a vehicle for the ambitions of Aaron Burr and Martin Van Buren. Tweed took over as grand sachem in 1863, but even with the Civil War at its height he couldn’t get New York’s Democrats to unite wholeheartedly around the Union. (Tweed surely would appreciate today’s quarrelsome and divided New York Democrats, who pride themselves on having purged the party of bosses.) So much for party discipline.

Sure, Tweed showed some shrewd political instincts when he reached out to the city’s growing Catholic—and mostly Irish—immigrants at a time when nativism was still in fashion. Not surprisingly, Tweed’s popularity among Irish Catholics was immense, so much so that a good many people assume, for reasons that suggest themselves, that he, too, was Irish Catholic. He was in fact a Scottish Presbyterian who knew how to count.

But his name is kept alive in history books because he became a poster boy for postCivil War corruption. The courthouse he and his men used as a vehicle for kickbacks became a symbol of Tweed’s rampage through the city treasury. The images are true enough, but some of Tweed’s successors—Richard Croker comes to mind —probably outdid the Boss in personal enrichment. And Tweed’s corruption, while appalling, in some ways pales in comparison with the Gilded Age scandals that have not earned so prominent a place in American history. Anyone who has read John Steele Gordon’s brilliant book about the Erie Railroad, The Scarlet Woman of Wall Street , might well conclude that compared with the ambitious financiers Jay Gould and Jim Fisk, Boss Tweed was a piker.

Ultimately, Tweed was not so much a political boss as a businessman whose trade was politics. It was Tweed’s successor, Honest John Kelly (he was called “honest” because he was not), who turned Tammany into a disciplined urban machine and established the model for machines from San Francisco to Kansas City to Chicago to Philadelphia.

Oh, and as for that famous courthouse that wound up costing New York thirteen million dollars in the 187Os, well, it’s still being used for municipal offices, and it seems solid enough. Meanwhile, city taxpayers recently were told that their School Construction Authority, which was created a dozen years ago in response to construction-related scandals—has spent seven billion dollars and gotten almost nothing done. One school, Erasmus High, was due for a twentytwo-million-dollar face-lift. The cost is now a hundred million and counting. Nobody, however, seems to know the names of the bosses involved.

Most Underrated Political Boss:

Ed Flynn, who was the leader of the Bronx Democratic party from 1922 until his death in Ireland in 1953. Flynn wins this contest by a nose over the better-known Charles Francis Murphy, who took over Tammany from the crooked Richard Croker and wound up fostaring the ca-1 reer of Al Smith and overseeing the implementation of the social reforms that became a blueprint for the New Deal.

By virtue of his close relationship with Franklin Roosevelt and Harry Truman, Flynn was the nation’s most powerful boss at the apogee of the American century. Truman’s biographer David McCullough describes Flynn as FDR’s favorite boss—this, of course, at a time when bosses were plentiful. He was an “urban,” “welleducated,” and “affable” pol, in McCullough’s words, who built on Murphy’s progressive record. He was part of Roosevelt’s inner circle, ran his campaign for a precedent-shattering third term, and was instrumental in easing Henry Wallace off the Roosevelt ticket in 1944. Flynn, McCullough observes, wasn’t put off by Wallace’s liberal politics, unlike most other members of Roosevelt’s Kitchen Cabinet. But Flynn didn’t get to be boss without knowing how to count, and Wallace didn’t add up. Flynn also was hardheaded enough to know that whoever ran as FDR’s Vice President in 1944 would wind up as President. He was for Harry Truman all along in 1944, and he used his considerable political clout to secure Truman’s nomination at that year’s Democratic National Convention.

As good an operator as he was, Flynn’s most important contribution came in the field of race relations. At a time when Southern Democrats were an important constituency, he pushed the party leftward on civil rights. Did he do it simply because blacks were an important voting bloc in New York? Perhaps. But that shouldn’t matter, at least not very much. Flynn supported Truman’s moves to desegregate the armed services and to make lynching a federal crime. And at the fractious Democratic National Convention in 1948, Flynn sided firmly with those, like the young mayor of Minneapolis, Hubert Humphrey, who believed that the party needed to make a firm stand on civil rights for blacks. The stand, of course, produced a boss’s nightmare—it split the party on the eve of a national election—but to Ed Flynn the party had no choice, for it was the right thing to do.

Some would describe Edward Joseph Flynn as the antithesis of a midcentury American boss, but that would be hasty and incorrect. Yes, he was better educated than many others, and more sophisticated, and certainly closer to national power. Nevertheless he ruled the Bronx just as surely and as firmly as the Pendergasts ran Kansas City and as Frank Hague ruled Jersey City. Flynn was a hard-boiled political professional with a great store of contempt for those he dismissed as “amateurs.” He represented, however, an often ignored side of the machine. In his hands the machine was not a vehicle for personal enrichment but a means of bringing democracy to the old urban neighborhoods (and of instilling a little discipline in the party ranks).

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