James Curley: Twice Convicted "Mayor of the Poor"

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In many political scandals, a representative accused of misconduct has been in office for decades, cultivating enough popularity that they can weather the blow to their image. James Michael Curley, by contrast, had his first stint in jail when his political career had barely started. Instead of ruining his future in the field, however, Curley's first scandal helped boost his popularity.

On December 2, 1902, Curley sat down to take a civil service exam. A member of the Massachusetts state house of representatives, Curley was not taking the exam on his own behalf; instead, he was impersonating a constituent who was trying to become a mail carrier. On February 25, 1903, he was arrested and charged with fraud. Along with an associate named Thomas Curley (no relation) he was convicted on April 3.

Curley was sentenced to serve 60 days in jail, and began his sentence on November 7, 1904, after a series of unsuccessful appeals. In response, hundreds of citizens demonstrated in the streets of Boston to show their support for him. The civil service examination system had been criticized as setting unnecessarily high educational requirements for jobs, a major concern for the Irish population in the city that considered the system to be unfairly weighted against them.

While still in jail, Curley won the Democratic primary by a margin of roughly 1,200 votes of more than 3,200 ballots cast. He won the subsequent general election as well, and would serve on the board of aldermen until 1910. "He Did It For a Friend" became a campaign rallying cry which handily disarmed any criticism about Curley's criminal record.

A towering figure in Boston politics, Curley was well-loved by a populace that saw him as their personal friend and advocate. However, he also had more than one run-in with the law and lived long enough to see his influence and appeal slowly wane away.

Early life

James Michael Curley was born in Boston on November 20, 1874 and attended the city's public schools. His father, who had immigrated to the United States in 1865 at the age of 15, died after lifting a heavy curbstone when Curley was just 10 years old. The incident helped stoke what would be Curley's enduring hatred for Boston's political power players, since the boss for his own ward did little to help the family after their breadwinner passed away.

Curley's mother helped the family stay afloat by working as a cleaning woman. Curley, already contributing to the family income by working as a newsboy, started jobs at a marketplace and drugstore as well. He then became a delivery driver, continuing his education by attending night classes twice a week.

Curley also worked as a salesman with the bakers' and confectioners' supply firm Logan, Johnston & Co., and held jobs in real estate and the insurance business. He entered politics in 1898, unsuccessfully running for Boston's city council, before winning a seat the next year.

Following his successful jailhouse campaign in 1904, Curley served on the board of aldermen until 1910 before returning to the city council. In the midst of these campaigns, he married his first wife, Mary E. Herlihy, in 1906.

In 1910, Curley entered his district's congressional race. In the Democratic primary, he competed against incumbent Representative Joseph O'Connell as well as a former congressman, William McNary. Curley made humility a staple of his campaign. When he found that his opponents had bought up all of the billboards in the district, he simply adorned them with streamers reading, "Elect a Humble Man: James Michael Curley." Although he came under fire for his personal honesty, especially given his criminal record, Curley vowed not to run a negative campaign against his opponents.

The strategy worked. After winning the primary, Curley was chosen in the general election for a House of Representatives term starting in March 1911.

Curley vs. Honey Fitz

While his election to Congress was a major milestone, Curley's primary objective was to become mayor of Boston. In November 1913, while still in the House, he announced that he would run for this position.

The incumbent mayor, John F. Fitzgerald (grandfather of President John F. Kennedy), had privately promised Curley that he would not seek re-election. But when he was pressured by the city's Democratic bosses to run for another term, Fitzgerald gave in. Rather than abandon his campaign, Curley decided that he would challenge Fitzgerald in the Democratic primary. He spurned the support of the party bosses, even vowing to end bossism if he was elected.

John F. Fitzgerald, aka "Honey Fitz," at left with son-in-law Joe Kennedy Sr. and grandson John F. Kennedy (Source)

Curley found a source of leverage in Fitzgerald's extramarital activities. The discovery that "Honey Fitz" had been canoodling with Elizabeth Ryan, an entertainer and cigarette girl nicknamed Toodles, at the Ferncroft Inn helped torpedo the mayor's chances of an electoral victory. Curley stoked the sensational coverage by delivering lectures with titles such as "Great Lovers in History: From Cleopatra to Toodles." On December 18, Fitzgerald withdrew his name from consideration.

The mayor's withdrawal did not solidify support behind Curley. He was annoyed when the Boston city council, dominated by Democrats, endorsed the man chosen to run in Fitzgerald's place (city councilor Thomas Kenny) instead of him. He became more confrontational during the campaign. When hecklers disrupted one appearance, he denounced them as "second story workers, milk bottle robbers, and doormat thieves." Jeered at another appearance, he asked the audience if anyone wanted to come onstage to "make anything of it." He had reportedly already laid one heckler flat with a punch before issuing this declaration.

Curley was also not above unscrupulous tactics during his campaign. Among other tactics, he mailed out notices to areas considered to be Kenny strongholds giving them incorrect information on where to find their polling place. Curley is credited with coining the phrase "Vote early and vote often."

In the final vote, Curley earned 43,262 votes to Kenny's 37,522. He had resigned from the House, effective February 4, to take on his new duties.

"Mayor of the poor"

Curley would sporadically serve as mayor, or throw his name into consideration for the position, for the next four decades. But under the city's reform charter, he found himself wielding immense power during his first term. He ousted hundreds of officeholders appointed by Fitzgerald, and personally met with any citizen who came in asking for a job or favor.

Targeted by political bosses and the business community, which quickly realized that Curley would favor Boston's poorer citizens over them, Curley lost the 1917 election to Andrew Peters, a figure in President Woodrow Wilson's administration. The state legislature, alarmed by the extent of Curley's mayoral power, responded in 1918 by barring Boston mayors from running for re-election; while they would be able to compete in future elections, they could only serve one term at a time. The legislation would stand for 20 years.

Following his defeat, Curley ran unsuccessfully for the House of Representatives in 1918 before becoming president of the Hibernia Savings Bank in Boston. But he soon turned his attention back to the mayor's office. The race again proved bitter; Curley ran a brutally negative campaign against his opponent, a Catholic lawyer named John R. Murphy. He sent canvassers posing as Baptist supporters of Murphy into Catholic districts to help raise suspicion of the candidate, or had them spread a rumor that Murphy intended to divorce his wife to marry a 16-year-old girl. On December 13, 1921, he was elected by a narrow margin of approximately 2,500 votes out of about 146,000 cast. His second term lasted from 1922 to 1926.

During his term, Curley won acclaim as a "man of the people" or "mayor of the poor" for his efforts to provide Boston's impoverished residents with jobs or other benefits. During the early 20th century, Boston was a city in decline. Shipping at the harbor was not as robust as it once was, the downtown was in a depressed state, and industries were departing.

One of the first actions Curley took in office was to order long handled mops for the cleaning women of City Hall so they wouldn't have to scrub the floors on their hands and knees. He sought to connect those looking to work with jobs that would benefit the city, including raking leaves, shoveling snow, reseeding the grass at cemeteries, and cataloging books at the library. During his second term, he oversaw a number of public improvements including the construction of schools, the L Street Bathhouse complex in South Boston, 12 new parks, health care relief stations, and hospital improvements.

Curley also sought to make residential properties in Boston more affordable by keeping their assessments low while raising assessments on downtown properties. Naturally, the tactic of taxing wealthier neighborhoods to help poorer ones put the mayor at odds with the business community. The disdain was mutual; one story, perhaps exaggerated or apocryphal, holds that Curley berated the president of the First National Bank after he refused to loan money to the city, even threatening to open the city's water mains to flood the bank's basement and vaults if they did not comply.

Later analyses suggested that this strategy may have helped accelerate the degradation of Boston's downtown. Looking to escape Curley's onerous tax assessments, businesses fled to the suburbs and left empty storefronts in their wake. This urban blight would not be remedied until the 1960s.

Despite his image as an advocate for the city's downtrodden residents, there were also indicators that Curley found unscrupulous ways to build his own wealth. Despite earning a salary of only $10,000 a year during his first term as mayor, he managed to have an ostentatious neo-Georgian mansion built for himself on Jamaicaway. He moved into the residence, which prominently featured shamrocks carved into the shutters, in 1915.

Curley's Jamaicaway mansion (Source)

During one mayoral stint, Curley was charged with stealing from the city through a scheme involving bond sales and a friend he had appointed as city treasurer. After the case dragged on through 34 continuances, he was finally ordered to pay $42,629 back into Boston's coffers in $500 weekly installments, with interest.

Remarkably, this instance of malfeasance also failed to shake the faith of Curley's most ardent supporters. Some years later, he made a radio address appealing for assistance with the repayment, saying he was having trouble making ends meet. In effect, he was asking Bostonians to contribute their own cash to help him repay public funds he had stolen. His adoring followers answered in droves, visiting the Jamaicaway mansion to drop off what cash they could spare.

The Roosevelt years

In 1924, in the midst of his second term in office, Curley entered the Massachusetts gubernatorial race. But his popularity in Boston did not extend to the rest of the state as a whole. He was soundly trounced by Republican candidate Alvan Fuller, earning 282,000 votes to Fuller's 641,000.

This campaign would result in another physical confrontation involving Curley two years later. Curley had helped a publisher named Frederick Enwright to launch a tabloid newspaper in 1921, and Enwright had returned the favor by having the paper endorse Curley in the 1924 election - the only one of Boston's six dailies to do so. But the relationship soured as each man accused the other of owing money, and the newspaper's coverage of Curley quickly turned negative.

On October 4, 1926, Curley spotted Enwright having lunch in the financial district and surprised him with an uppercut. While Curley would later claim that he had acted in self-defense, Enwright said he had been sucker punched. His Boston Telegraph soon ran an editorial cartoon portraying Curley as an inmate and a drunkard who had learned to hit from behind as a street fighter. Curley promptly filed a libel suit, and the jury ruled in his favor.

Prohibited from running for re-election under the 1918 state law, Curley had to wait until 1929 for his next chance at the office. He was again voted in, tallying up 117,084 ballots against Republican challenger Frederick Mansfield's 96,626. The election was held just one week after Black Tuesday, the catastrophic stock market crash that marked the start of the Great Depression.

Curley's latest four-year term began in January 1930. His abrasive personality resulted in a clash with Governor Joseph Ely over how relief programs would be administered. Boston would be allocated 12,500 jobs under the Public Works Administration, a little more than half of what the city was actually entitled to.

In the lead-up to the 1932 presidential election, Curley opted to support Franklin D. Roosevelt over Al Smith for the Democratic nomination. This marked a strong departure from his constituency, since Smith, a former New York governor and the Democratic candidate in 1928, was the preferred choice of most of the city's sizable Catholic population. At the party convention, Curley somehow managed to attend as a delegate representing Puerto Rico and threw his support behind FDR.

Curley and FDR (Source)

Following FDR's nomination and subsequent victory in the general election, Curley expected that he would be rewarded with a plum political position. In particular, he was hoping to be named ambassador to Italy. Instead, the newly elected President offered him the less appealing role of ambassador to Poland. A disappointed Curley rejected the offer with a quote from Shakespeare's Henry VIII, pointedly charging that FDR "left me naked to mine enemies."

The tiff with FDR was short-lived. With enthusiasm for Democratic candidates running high, Curley was able to decisively win the 1934 gubernatorial election. About 736,000 Massachusetts residents voted for him, while 627,000 opted for Republican candidate Caspar Griswold Bacon and 94,000 went for third party candidate Frank Goodwin.

As governor of Massachusetts, Curley oversaw FDR's New Deal programs and bolstered them with his own state relief programs. He focused on infrastructure, spending large sums to improve roads and bridges. However, a later analysis suggested that he may have unnecessarily delayed New Deal programs in the state by squabbling with federal authorities over who would control the funding.

In the late 1930s, Curley's influence began to falter for a time. In 1936, while still governor, he ran for a Senate seat but lost to Republican candidate Henry Cabot Lodge Jr. He was also defeated in his attempts to return to the Boston mayoral office in 1937 and 1941, and in 1938 won the Democratic nomination for governor but lost the general election. However, he was successful in the 1942 race for the House of Representatives and won re-election two years later.

Fraud conviction

In the 1945 election, Curley was returned to the Boston mayor's office on a landslide count of 111,824 votes. It was more than both of his opponents combined.

This victory was all the more remarkable because Curley was under federal indictment at the time. His trial had even been postponed to allow him to run for office.

Curley had participated in Engineers Group Inc., a fraudulent organization that misrepresented its resources in order to win war contracts for clients. Curley's role in the scheme had been fairly minimal; he had simply let the organization use his name on their letterhead, and he would argue that he had been the "victim of a professional confidence man whose professions of honesty deceived me and others." But he had still collected $60,000 in government funds by attaching his name to the group. The scheme was uncovered during then-Senator Harry S. Truman's investigation into the U.S. national defense program.

In February 1946, just a month into his fourth term as mayor, Curley was convicted of 10 counts of mail fraud. Also convicted were Donald Wakefield Smith, a former member of the National Relations Board, and James G. Fuller, who had acted as the vice president of Engineers Group Inc.

Curley continued to serve as mayor as his case went through the appeals process. He finally ran out of options when the Supreme Court opted not to consider his arguments. In June 1947, he was sentenced to serve six to 18 months behind bars. In poor health, Curley disregarded his doctor's orders and traveled to the nation's capital to personally request that the sentence be suspended; a federal judge refused, and Curley began serving his sentence in federal prison in Danbury, Connecticut.

While a criminal conviction is typically enough to get a politician to resign their office, Curley refused to step down. City Clerk John B. Hynes served as acting mayor during Curley's imprisonment; at Curley's direction, he collected the mayor's salary but donated it to charity. It is unclear just how much influence he continued to have from his out-of-state jail cell.

Similar to the public outcry in support of Curley after his previous fraud conviction, his latest plight inspired mass demonstrations among his supporters. Bostonians protested in the streets, and more than 172,000 people (about a quarter of the city's population) signed a petition demanding clemency "because of his health and other extenuating circumstances."

The entire Massachusetts congressional delegation also indicated their support for a pardon, with one notable exception: John Fitzgerald Kennedy, who had succeeded Curley as a congressman and would go on to be elected President in 1960. The action was widely scene as a rebuke to Curley for how he had treated Kennedy's grandfather. However, other accounts suggested that Kennedy was skeptical about Curley's claims of illness, or did not want to give the mayor special treatment when he had turned down appeals by the families of other prisoners.

The day before Thanksgiving, President Harry Truman commuted Curley's sentence. The mayor had served five months of his sentence, just shy of its minimum term. The action was ostensibly due to Curley's poor health, including fears that he would die in prison if he wasn't released. However, it is more likely that Truman acted under pressure from Curley's constituents and the Massachusetts delegation. After all, Curley was able to quickly return to work after his release.

Despite receiving a warm welcome upon his return to Boston, Curley also doomed his future in the office with an off-the-cuff remark. Soon after resuming his mayoral duties, he quipped that he had accomplished more in one day than Hynes had done in five months. Offended by the remark, Hynes decided to challenge Curley in the 1949 election.

John B. Hynes (Source)

The restriction on running for re-election had been lifted, so Curley was trying to hold on to the mayor's office for the first time since 1917. He denounced Hynes as a candidate who would favor Boston's businesses over its people. Hynes fired back that Curley was out of touch.

By this point, Curley's influence had also waned considerably; an increasing number of voters knew him more for his fraud conviction than for his earlier advocacy for the poor. Despite garnering just over 126,000 votes, he lost to Hynes by about 11,000 votes.

Later life

Soon after this defeat, a dual tragedy struck the Curley household. On February 11, 1950, his 41-year-old daughter Mary suddenly died of a cerebral hemorrhage while talking to her 34-year-old brother Leo on the phone. Later in the same day, Leo collapsed and died of the same ailment after learning of his sister's death.

Curley was no stranger to this kind of loss. His first wife had died on June 10, 1930, and in 1937 he re-married to a woman named Gertrude Marion Dennis. Curley had nine children altogether, but would outlive seven of them. Five died before the age of 40, including twin sons who died shortly after their birth in 1921.

On April 14, 1950, Truman issued Curley a pardon for both his 1903 fraud conviction and his more recent conviction. It was essentially a favor, a way of offering Curley a clear slate; the charges hadn't included any lasting sanctions, since he could still vote and hold office under Massachusetts law.

Curley launched two more mayoral bids in 1951 and 1955, both unsuccessful. In 1957, he was appointed to the State Labor Relations Commission. His memoir, I'd Do It Again!, was published in the same year; he'd earlier published another autobiographical work, The Purple Shamrock, with journalist Joseph Dinneen. In 1958, the movie The Last Hurrah was released, based on a book written about Curley by Edwin O'Connor. Spencer Tracy played the lead.

Curley died in Boston on November 12, 1958. Following his death, he lay in state at the State House Hall of Flags; he was only the fourth person in Massachusetts history to do so.


Sources: The Biographical Directory of the United States Congress, "Curley Gets Prison for Mail Fraud" in the Deseret News on Feb. 18 1946, "Truman to Free Curley Tonight" in the Lawrence Journal-World on Nov. 26 1947, "Truman Pardons Ex-Mayor Curley" in the Medera Tribune on Apr. 14 1950, "The Last of The Bosses" in American Heritage in June 1959, "Boston's Powerful Rogue" in the Christian Science Monitor on Dec. 29 1992, "How to Govern From Jail" on Slate on Dec. 2 2004, "The Mayor of the Poor" in CommonWealth on Sep. 22 2013, "The First Mayor of the New Boston" in CommonWealth on Sep. 25 2013, The Fitzgeralds and the Kennedys: An American Saga by Doris Kearns Goodwin, James Michael Curley: A Short Biography with Personal Reminiscences by William Bulger, John William McCormack: A Political Biography by Garrison Nelson, Rogues and Redeemers: When Politics Was King in Irish Boston by Gerard O'Neill