Tom Dewey in the 
Second Circuit

Legal History

Tom Dewey in the 
Second Circuit

By C. Evan Stewart

2-25-15 C  Evan Stewart For most lawyers active today in the Second Circuit, Thomas E. Dewey is a faint memory.  He was, of course, almost President of the United States (twice nominated by the Republicans, first in 1944 and then in 1948), a three-term Governor of New York State (1943-54), instrumental in making Dwight D. Eisenhower President in 1952 (and Richard M. Nixon his Vice President), mentor of many of the 20th Century’s most famous lawyers (e.g., John A. Wells, Frank Hogan, J. Edward Lumbard, Charles Breitel, Lawrence Walsh, William Rogers), recipient of the Federal Bar Council’s Emory Buckner Medal (in 1968), and senior partner of the prominent law firm Dewey, Ballentine, Bushby, Palmer & Wood.  The focus of this article, however, is on his pre-political career in the law, which, because of his success and prominence, catapulted him into the public spotlight, where he remained for decades.

Dewey’s Legal Education

Born in 1902 in Owosso, Michigan, Dewey began his higher education at the University of Michigan.  Besides his studies, his main focus was on his promising singing career, in which his voice was praised for its “velvety texture.”  After winning a statewide competition in his senior year (and, thereafter, finishing third in the national finals), Dewey decided to enroll in Michigan Law School, while continuing his vocal training.

Whether it was because of his divided focus or not, Dewey found his first year studies little more than “scrivener’s work.”  Upon completion of his One L, Dewey shipped off to Chicago that summer for more singing training.  This, in turn, led him to bigger and better things in New York City; with that came Dewey’s transfer to Columbia Law School.  While at Columbia, Dewey augmented his income by singing in churches and synagogues.  A bad performance at a public recital (caused by laryngitis), however, caused him to rethink his future plans.

Focusing more on his legal studies, Dewey’s grades, class rank, and standing among his classmates and peers (e.g., William O. Douglas) began to soar.  When it came time to apply to Wall Street law firms, Dewey visited many of the usual suspects, but found the experience less than dazzling (at White and Case, for example, he was told, “Of course, you … realize that we regard a young man as nothing but a pair of legs the first two years.”)  Ultimately, he received three offers (the going rate: $35 per week); he decided to accept the one proffered by Larkin, Rathbone and Perry, a 36 lawyer firm that focused mainly on corporate leasing work.

Law Practice

For Dewey, who wanted to try cases, the work was tedious and unstimulating.  To make matters worse, he soon found himself at odds with one of the firm’s senior partners.  After one year, his services were terminated.

Fortunately, Dewey was able to find a job at the small firm of McNamara & Seymour, even though Mr. McNamara worried that Dewey might be “a little too bumptious.”  Dewey’s prickly temperament did cause some problems for him in such a small office, but his undeniable talent and thoroughness also were recognized – so much so that McNamara assigned Dewey to handle an important customer lawsuit against one of the firm’s largest clients, Empire Trust Company.  As the case got closer to picking a jury, Dewey was prevailed on to “second chair” the matter in deference to a very experienced trial lawyer, George Z. Medalie.

This “in the trenches” experience proved to be a career altering event for the young attorney.  Not only did Dewey impress his mentor (who soon was calling Dewey a “legal prodigy”), but when Medalie was nominated to become the U.S. Attorney in January 1931, he made a point of telling Dewey he wanted him to join his staff.  Dewey went a step further:  He convinced his boss to appoint him as the U.S. Attorney’s chief assistant.

The U.S. Attorney’s Office

Dewey’s track record in that job was a bit mixed at the beginning.  Everyone was aware of and appreciated his intelligence, attention to detail, and quest for perfection.  At the same time, however, many considered him arrogant and difficult to deal with, especially given that the chief assistant was exercising authority over a number of vastly more experienced lawyers.  Fortunately for Dewey, he was able to shift his focus to actual trial work.  In the first case in which he acted as “first chair,” Dewey prevailed in a criminal prosecution against James Quinliven, a corrupt member of New York City’s Vice Squad.

A particular focus of the U.S. Attorney was the pervasive grip of organized crime over the city. He tasked Dewey to head up a squad to go after those gangsters who might have exposure to income tax evasion charges.  One such target was Joseph Castaldo, who, because of his efforts to illegally corner the market on artichokes in New York City, became known as the Artichoke King.  After one day’s evidence at trial, the King threw in the towel and pled guilty.

In the midst of Dewey’s attempt to systematically assemble evidence and begin to prosecute numerous bad guys in New York City, Medalie took a leave of absence from his post to run for the U.S. Senate in 1932.  That left Dewey in de-facto charge of the office.  Besides his political efforts to help Medalie in a decidedly un-Republican year, Dewey chose to go after Waxey Gordon.  Gordon was a street urchin turned major league bootlegger.  He had earned multiple millions with barely a nod to the Internal Revenue Service (in 1930, for example, Gordon paid the IRS $10.76).  Because Gordon had hidden his wealth in more than 200 bank accounts, none of which bore his moniker, it took a Herculean effort to put all the paper pieces together. While Dewey and his staff were engaged in that effort, various members of Gordon’s gang were found dead on the eve of their grand jury appearances.

Two days into Gordon’s trial in November 1933, Medalie resigned his post.  President Roosevelt, who had been inaugurated in March, had yet to name a new U.S. Attorney; as such, the judges of the Southern District (invoking an 1894 precedent) acted quickly and unanimously named Dewey the interim U.S. Attorney.  Dewey left the courtroom to be sworn in and then returned to continue the prosecution.

A critical witness for the prosecution was Helen Denbeck, a short order waitress at a restaurant near a garage owned by Gordon.  She described in great detail the comings and goings of Gordon’s beer trucks.  How did she know they carried beer?  “I smelled the beer.”  How did she know what beer smelled like? “I drink lots of beer.  I know how it smells, too.”  Denbeck then identified a number of Gordon’s key henchmen when shown pictures:  “Frankie the Chauffeur,” “Joe the Fleabag,” etc.

Exasperated by the level of detail she provided, Gordon’s lawyer blew himself up on cross:  “You know everybody….  Next you’ll be telling us you know an Oscar!”  Denbeck’s answer?  “Sure, Oscar Brockert.  He was Waxey’s brewmaster.”

The jury deliberated for under an hour.  Gordon was sentenced to 10 years and received an $80,000 fine.   The trial judge was effusive in his praise of Dewey and his trial team.  Dewey, in turn, issued a public warning to Gordon and his colleagues not to harm any witnesses who had testified at the trial.

The case made newspaper headlines across the country and Dewey not only made a national radio address broadcast thereafter, he also was prominently featured in news segments in movie theaters.  Five weeks later, President Roosevelt named a Democrat to succeed Dewey.  Dewey exited public life determined one day to head up a leading Wall Street law firm and “make a hell of a lot of money.”

Next Steps: The Special 

Dewey went back to private practice, opening up his own law offices at 120 Broadway.  Not only did his practice flourish, but his ability to remain in the public eye continued.  For example, he was retained by the New York Bar Association to bring proceedings against Municipal Judge Harold L. Kuntsler, who somehow had deposited $166,000 into his bank account over a fairly short period of time.  On Dewey’s cross, Kuntsler’s explanations for the 107 separate deposit slips consisted of “I don’t know” and “I can’t remember.”  Before the trial concluded, Kuntsler resigned on the grounds that “his usefulness had been impaired” by all the brouhaha.  A week later, Kuntsler skipped town with an ex-prostitute, who later accused him of stealing her jewels.

In 1935, a newly appointed grand jury, constituted to investigate the “numbers racket” (a/k/a the “policy racket” – the pervasive corruption that permeated all of New York City), would change Dewey’s trajectory.  The duly elected District Attorney for Manhattan, William C. Dodge, was a Tammany Hall creature (the Democratic Boss, Jimmy Hines, called him “stupid, respectable, and my man”). The grand jury not only excluded Dodge from its deliberations, but went even further:  It demanded a new prosecutor.  After much politicking (including, it would appear, William O. Douglas, then the head of the Securities and Exchange Commission, who vouched for his old law school classmate to President Roosevelt), Governor Herbert Lehman announced that because all of his other choices had turned him down he was amenable to “Thomas A. Dewey” being appointed Special Prosecutor to address New York’s rackets (costing the taxpayers upwards of $100 million per year).  On July 1, 1935, Dewey, after demanding (and getting) complete independence from Dodge, agreed to the appointment.

Initially, he was a general without an army.  Dewey, however, quickly and skillfully moved to consolidate political heft behind his new office, enlisting the support of Mayor Fiorello La Guardia, Secretary of the Treasury Henry Morgenthau, U.S. Attorney General Homer Cummings, FBI Director J. Edgar Hoover, U.S. Attorney for the Southern District Frank Adams, Arthur Sulzberger of The New York Times, and Governor Lehman.  With that support, he was able to get the city’s Board of Estimate to give his office a five month budget of $121,000.  But, he still needed troops.
To that end, Dewey was besieged by thousands of lawyers, hundreds of accountants, investigators, and secretaries, as well as scores of others (e.g., dentists, bricklayers, ex-baseball players) who just wanted to make a difference.  Eventually, Dewey hired a staff of more than 60 individuals, a group that included a number of old hands from the U.S. Attorney’s office (e.g., Murray Gurfein), as well as a number of young, unknown attorneys (e.g., Charles Breitel, Stanley Fuld, Frank Hogan).

Dewey was very stern with his chosen group, advising them not to fall prey to any kind of inducements that might be waved in their direction:  “If you want to have a good time, go to New Jersey!”  To the people of New York, he promised to “prosecute every crime which is part of an organized racket … every crime in the book, from conspiracies and malicious mischief to assault in the first degree, from extortion to perjury, from income tax violation all the way to murder.”

The first order of business was to figure out who was who and what was what in New York City’s rackets.  With incredible diligence, Dewey’s staff assembled a comprehensive chart, listing 25,000 names and covering every conceivable racket.  The Dewey team then proceeded to track down each lead and every tip, following up on each wiretap and every surveillance.  Soon, the office had a mountain of evidence, and its first target was Dutch Schultz (a/k/a Arthur Flegenheimer), New York’s most flamboyant gangster.

Dutch’s reaction to Dewey’s focus was to the point: He decided to assassinate the Special Prosecutor.  Unfortunately for Dutch, he offered the hit to Albert Anastasia, who promptly told Lucky Luciano (a/k/a Salvatore Lucania), the de facto head of the Mafia in New York.  Luciano hated publicity and had not been happy with the negative media hullabaloo that Schultz’s violent tactics had engendered.  When he conferred with his fellow Mafia chieftains, to a man they agreed that Schultz’s assassination plot against Dewey could not be countenanced; with one demurrer, they also agreed that it would be best for Schultz to be hit instead (Meyer Lansky dissented, offering prescient advice to Luciano:  “Right now, Schultz is your cover.  If Dutch is eliminated, you’re gonna stand out like a naked guy who just lost his clothes.”) With the contract thus assigned, Schultz and a number of his gang met their end on October 23, 1935 at the Palace Chop House and Tavern in Newark, New Jersey.  That eliminated one problem, but Lansky proved correct:  with Schultz gone, Dewey turned his focus on Luciano.

Dewey’s means of getting to Luciano? A full-court press against the extensive prostitution operation that was overseen (ultimately) by Luciano.  Luciano’s initial reaction was one of indignation:  “I may not be the most moral and upright man that lives, but I have not stooped so low as to become involved in aiding prostitution.”  After a Rube Goldberg-like extradition from Arkansas, Luciano was arraigned back in New York City, with $250,000 in bail imposed, and a trial set for May 1936.

To the jury, Dewey explained the difficult row he had to hoe:  “Frankly, my witnesses are prostitutes, madams, heels, pimps, and ex-convicts….  We can’t get bishops to testify in a case involving prostitution….  We have to use the testimony of bad men to convict other bad men.”  Dewey’s other challenge was to tie Luciano directly to the acts of others far below him in the underworld’s food chain.

Prostitute after prostitute testified to the degrading life style in which they worked.  Crucial to Dewey’s case, however, was Cokey Flo Brown, who not only knew Luciano but also was able to testify about his direct involvement (including putting madams on salaries).  Equally important, she held up under a withering cross-examination by defense counsel – an ordeal made more difficult by the fact that she was in the midst of withdrawal from addiction to heroin.  Luciano then testified in his own behalf, avowing on direct examination that he knew none of the prostitutes who had testified and had no involvement in such an unsavory racket.  On cross-examination, Dewey tried to skewer Luciano’s reputation for truthfulness by going through his litany of run-ins with the law and his track record for veracity.  As compelling as it was, there was no Perry Mason moment, and certainly no admission of guilt by Luciano.  Indeed, in his closing Dewey had to acknowledge that “he hadn’t proved that Luciano was himself putting women into houses of prostitution.”  But Dewey had proven Luciano to be “the greatest gangster in America,” and he pleaded with the jury to “[c]onvict him, in the name of the safety of the people of this city.” And convict him the jury did.

Having brought down Luciano, Dewey did not rest on his laurels; he continued to press on against the multiple rackets operating throughout the city.  But he was bone-weary, and his personal finances were down to $300.  As a result, when John Foster Dulles offered Dewey a partnership at Sullivan & Cromwell in 1937 worth $150,000 per year, Dewey quickly agreed.  Shortly thereafter, however, in response to Republican overtures and implorings, Dewey also agreed to take on the party’s nomination for Manhattan District Attorney.  (Dewey went back to Dulles, who quickly concurred with this change of plans:  Dewey “had to do it.”)

Politics and the Law

Dewey jumped into politics with both feet, addressing up to 10 audiences a night.  Extremely well-financed by the Republican establishment, his formidable campaign organization helped the new politician become familiar with the ethno-cultural, tribal nature of the city’s electorate.  Dewey soon found that he enjoyed the game and he proved effective at retail politics; ultimately, he outpolled the Tammany Hall candidate by over 100,000 votes.
Shifting his prosecutors and staff just a few blocks to the Manhattan District Attorney’s office, Dewey hit the ground running, first cleaning up the mess at the Tombs and instituting innovations to ensure effective defense counsel to those in need.  Then he turned for another big scalp; this time, however, it was one who wore a white collar.

Richard Whitney, one of Wall Street’s most prominent financiers (and former head of the New York Stock Exchange), was not only in dire straits financially, but he also had engaged in wrongdoing to try to stay one step ahead of his creditors.  On March 9, 1938, Dewey announced Whitney’s indictment for stealing over $100,000 from his wife’s trust fund.  When SEC Chairman William O. Douglas reported the news to President Roosevelt (an old friend of Whitney’s; both had gone to Groton and Harvard), his anguished response was, “No. Not Dickie Whitney! …  I can’t believe it.”  The trust fund turned out not to be Whitney’s only theft; ultimately, he spent several years in Sing Sing.

Dewey next took aim at James J. Hines, the legendary head of Tammany Hall.  Indicted on conspiracy charges involving an illegal lottery and corrupt judges, Hines retained prominent attorney Lloyd Paul Stryker.  Dewey versus Stryker promised to be what the tabloids called “The Battle of the Century.”  And Hines himself was no Luciano-style defendant (famed corruption fighter Samuel Seabury had said, “Jimmy Hines is the most likeable rogue I know.”).

Once the trial began, Dewey encountered another opponent:  Judge Ferdinand Pecora.  The judge hoped for the Democratic nomination for governor in 1938 (which would be open, if Governor Lehman opted to run for the Senate), and was led to believe by White House operatives that President Roosevelt would favor him if he ran roughshod over Dewey (thus, perhaps derailing Dewey’s ambitions for higher political office).  As such, the District Attorney often found himself on the losing end of many rulings during the trial.

But all the pyrotechnics among Dewey, Stryker, and Pecora could not obfuscate the mounting evidence of Hines’ financial arrangements with Dutch Schultz and other mobsters that came in before the jury.  Hines’ former lawyer Dixie Davis (“Kid Mouthpiece”) was a key witness against Hines.  Notwithstanding, Pecora declared a mistrial based on one fairly innocuous question Dewey asked a Stryker witness on cross. The judge’s ruling was on shaky ground (to say the least), but, as Dewey acknowledged, “unfortunately, … the People of the State of New York have no appeal from this or any other of the decisions in this case.”  To his troops, Dewey was not cowed, declaring, “Let’s get to work.  There’ll be another trial.  And we’ll win it.”

The setback did not seem to impact Dewey’s public profile; in September 1938, New York Republicans fell all over themselves to nominate him to run for governor.  Dewey embraced the new role, telling his mother, “I can do so much more for all of the things I believe in and have fought for if I am Governor than if I am merely the District Attorney of one of 62 counties of New York.”  Dewey ran a compelling race against the formidable incumbent, Herbert Lehman (who had been persuaded not to run for the Senate).  Perhaps if President Roosevelt had not interjected himself late into the campaign, contending that the Republicans were waging an anti-Semitic campaign against Lehman, Dewey might have won.  As it was, he lost by only 64,000 votes (carrying every county outside of New York City except one).  This was widely viewed as a victorious defeat; indeed, it set the stage for Dewey’s ambitions at the national level.

While balancing his growing national fame (and calls for him to run for President in 1940), Dewey realized he still had to produce in his day job.  Dewey next took on corruption in the subway system, as well as in the oversight of the city’s taxicabs.  Then, in January 1939, he was back in court to prosecute Hines.  One piece of good news was that Judge Pecora would not preside.  On the negative side:  A key prosecution witness had committed suicide. Dewey’s team solved that problem, however, by reading into the record at the second trial his testimony from the first trial.  All the other evidence from the first trial also was brought before the jury.

Putting his predecessor William C. Dodge through the wringer on the stand, Dewey asked him whether he had a mother-son relationship with Hines.  Dodge retorted, “I’ve never been a mother.  I can’t say.”  That bought guffaws from those in the courtroom, but Dodge had been set up because Dewey then produced prior Dodge testimony where he had in fact described his relationship with the Tammany leader in precisely those terms.  As things went south, Stryker took a gamble and decided not to put his client on the stand.  Presumably, that did not sit well with the jury, which quickly convicted Hines on February 24, 1939.

The national headlines for this latest victory now made Dewey a favorite in the 1940 presidential race (even out-polling President Roosevelt).  With a lot of Republican establishment support, he decided to make a run for the party’s nomination.  Dewey did well on the hustings (and in the primaries), but the growing war in Europe was probably too much of a hurdle for a “38 year old kid” with no foreign policy experience – and there also was the Wendell Wilkie phenomenon, which swept the Republican convention in Philadelphia.

Even though not nominated, Dewey was clearly a political comer.  He was active across the country in speaking against a third term for President Roosevelt.  Thereafter, he decided he would not run for re-election as district attorney, but instead would retire to private practice and then try for the New York governorship again in 1942.  To ensure a smooth transition, Dewey cut a deal with Tammany Hall whereby his able assistant Frank Hogan would be the Democratic candidate to succeed him.  Dewey’s last day in office was December 31, 1941, and he transitioned to private practice at 20 Exchange Place (Charles Breitel came with him).  His return to the law was a mere holding pattern, however, as Dewey focused like a laser on getting the gubernatorial nomination (which came to him at least as enthusiastically as had the 1938 nod).  Running against an uninspiring John J. Bennett (the state’s Democratic attorney general), Dewey won by an overwhelming 647,000 vote margin.

Dewey, Ballentine, Bushby, Palmer & Wood

It would be 12 years until Dewey would return to his original goals of running a prominent law firm and “mak[ing] a hell of a lot of money.”  After two unsuccessful tries for the Presidency in 1944 and 1948, he finished his third term as governor at the end of 1954.  Not interested in any formal role thereafter in public life, Dewey was recruited to be the savior of the Root Clark firm (see, Federal Bar Council Quarterly, August 2012), which, with the death of Emory Buckner and the departure of a number of key partners to start Cleary, Friendly, Gottlieb & Steen, was in serious decline.  Recast as Dewey, Ballentine, Bushby, Palmer & Wood, effective January 1, 1955, the firm took off like a rocket, with Dewey becoming a rainmaker of the first rank.  He never became President, but at least he did achieve his first two goals.


The best Dewey biography is by Richard Norton Smith, “Thomas E. Dewey and His Times” (Simon and Schuster 1982).  Other helpful materials on Dewey’s career include:  Stanley Walker’s “Dewey:  An American of This Century” (McGraw-Hill 1944); Mary Stulberg’s “Fighting Organized Crime:  Politics, Justice and the Legacy of Thomas E. Dewey” (Northeastern Univ. Press 1995); and Richard Hammer’s “Playboy’s Illustrated History of Organized Crime” (Playboy 1975).

Dewey’s showdown with Luciano quickly went Hollywood with Warner Brothers releasing Marked Woman in 1937.  Betty Davis starred as Mary Dwight (in the Cokey Flo Brown role); Mary’s “job” was sanitized a bit insofar as Davis portrayed a “hostess” in the nightclub of vice czar Johnny Vanning (Lucky Luciano), who was played by Eduardo Cianelli.  Humphrey Bogart co-starred in the Dewey role as crusading District Attorney David Graham.  One of the other “hostesses” was played by Mayo Methot, Bogart’s third wife, whom he would later divorce in order to marry Lauren Bacall.
Alice Roosevelt Longworth (Teddy’s daughter) was widely credited in 1944 with calling Dewey “the little man on the wedding cake.”  In fact, Democratic apparatchiks Isabel Kinnear Griffin and Helen Essary Murphy originated those damning words, and then attributed them to Longworth to help publicize them; Longworth never disabused people as to their actual source.  Regardless of origin, the image created was one that hurt Dewey with many voters, and he was never able to live it down.

Dewey appointed his mentor, George Medalie, to the N.Y. Court of Appeals on September 28, 1945, where he served until his death on March 6, 1946.  Gladys Heldman, the prominent tennis promoter (and founder of World Tennis magazine), was Medalie’s daughter.  Julie Heldman, who was once a highly ranked tennis professional (at one point No. 5 in the world), is Medalie’s granddaughter.

Upon joining his new firm in 1955, Dewey insisted not only that his name lead the masthead, but that at no time in the future, for whatever reason, could that status ever be changed.  Thus, when Dewey Ballentine merged with LeBoeuf Lamb, the firm was re-cast as Dewey & LeBoeuf.  With the merged firm’s messy collapse in 2012 and certain of its leadership under criminal indictment and imminent trial, those unfamiliar with Tom Dewey’s imposing career and legacy now only know his name in the media under the most unfortunate of circumstances.

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