William J. Flynn is one of the most fascinating US law enforcement and intelligence personalities of the early 20th century. Historian Jeffrey Simon has authored a long overdue biography of this illustrious and colorful man (Jeffrey D. Simon, Bulldog Detective: William J. Flynn and America’s First War Against the Mafia, Spies, and Terrorists, Prometheus Books, 2024). Born in 1867, Flynn grew up in New York City, where he remained his entire life and came to understand intricately. Flynn joined the US Secret Service (USSS) in 1897 and quickly rose through the ranks. Only four years into his career, he headed the Eastern Division.
William J. Flynn
Detective, Supersleuth, Director of both the US Secret Service and Bureau of Investigation (ca. 1918).
His exploits received excited news coverage, in part because Flynn freely gave interviews touting his achievements, in part because he wrote “first-person accounts of his adventures.” (ix) National papers reported on the “supersleuth,” who personally chased criminals up dark alleys and down fire escapes. In the public eye, Flynn was a real-life Gotham City superhero. After the successful prosecution of the Morello and Lupo crime families in 1910, Flynn was hired to reorganize the NYPD’s detective division, widely seen as corrupt and ineffective. After only six months Flynn left, succumbing to intense political infighting. He returned to the Secret Service. Despite his capitulation, Flynn instituted lasting changes in the NYPD and, for years to come, remained close to the detective force he had assembled.
In 1912, President William Howard Taft appointed Flynn to head the USSS. “Being a New Yorker through and through,” (87) Flynn refused to move to Washington, DC, and remained in New York. Simon noted, “As busy as Flynn was dealing with counterfeiters and protecting presidents, he still found time to write.” (89) Published in papers throughout the country, Flynn recounted his fights against the underworld in colorful prose. Albeit nominally neutral in the emerging World War, the US became the main supplier of war materials for Germany’s enemies. Germany responded by launching a sabotage campaign against US industry and shipping in 1915. New York became a key battleground.
Simon starts his monograph with the story of German Commercial Attaché Heinrich Albert, who lost his briefcase in an elevated train in New York in the summer of 1915, triggering a massive scandal. Simon uses the leading secondary literature dealing with German conspiracies in the neutrality years (1914–17) to recount one of the most unsettled periods in US history. The absence of primary sources, which reveal that Flynn radically exaggerated his role in fighting German spies during this period, leads to an uncritical view of the often historically inaccurate books Simon used to assemble the story. The Albert briefcase theft, for example, if even perpetrated by Flynn’s Secret Service, was a rogue operation in the best case. The USSS had the protection of the president and counterfeit investigations as its only authorized missions. The purported executive order of President Wilson expanding the Secret Service mission in May 1915 never existed, neither did the eleven-man counterintelligence force in New York Flynn supposedly organized and Simon describes. (See Studies in Intelligence 68, No 1 (March 2024): 21–34).
Heinrich Friedrich Albert
The German Commercial Attaché who lost his briefcase on the New York El in July 1915.
Chief Flynn made these claims in several books and movies about his wartime experiences after he left the Secret Service in 1917. In his 1931 autobiography, Flynn’s former boss, Secretary of the Treasury William Gibbs McAdoo seconded the claims, which formed the basis for the generally accepted story in subsequent historical accounts. One of the most controversial facets of Flynn’s career was his ambition to insert himself into Bureau of Investigation (BI, the forerunner of the FBI) turf. In his postwar writings, Flynn placed himself at the center of counterintelligence work in New York during the war. For example, he took credit for the Robert Fay case, a German sabotage agent, who was identified and arrested by the NYPD. Flynn never led the investigation. The same is true for counterintelligence successes of the BI he took credit for. His close connections to the NYPD offered him a venue to share or even usurp the limelight of the “German spy hunters.”
Flynn’s claims set up the thesis, that the USSS and the BI battled for control of counterintelligence in the US during the neutrality period. Yet, there was no battle between agencies. It was Chief Flynn’s battle alone as he craved public attention. While Simon leaves open the reasons for Flynn’s firing in 1917, it is documented and obvious: Flynn would not seize his interference in Bureau and Military Intelligence operations. As a result of his insubordination, Attorney General Gregory forced Treasury Secretary McAdoo to oust Flynn, which happened without warning via telegram (comparable to firing by tweet).
William Gibbs McAdoo
Secretary of Treasury, son-in-law of President Woodrow Wilson, with ambition to become president of the United States one day.
Flynn, soothing his hurt ego with widely publicized articles, books, and movies between 1918 and 1920, managed to briefly rekindle his career. President Wilson appointed the “Bulldog Detective” in 1919 to head the very organization he had loathed as Secret Service chief. Simon points out, that he, not J. Edgar Hoover, became the first Director of the Bureau of Investigation. (183) Arguably, William Allen was the first [acting] director of the agency. Promising to solve a string of terrorist attacks, including the 1920 Wall Street bombing, in which thirty people died, Flynn once again raised public expectations with exuberant proclamations. He did not solve these crimes and instead presided over the controversial Palmer Raids, mass arrests of suspected anarchists and communists.
The story of the red scare and the anarchist threat is the strongest part of Simon’s book. The author has written extensively about this topic. His thorough research and expertise shine brightly in this account. After only two years heading the BI, the Harding administration replaced Flynn with William Burns, a sleuth of similar public stature. Flynn’s career never recovered. He continued to write and publish accounts of his past accomplishments while operating a private detective agency. He died in 1928.
Simon celebrates Flynn as incorruptible, unmotivated by “financial rewards…, a straight shooter…,” lacking political ambitions (183-184) and blames “unrealistic expectations” for his failures. Yet it was Flynn who carefully curated his public image as the “supersleuth,” one of the underlaying causes of his enduring fame, which also set him up for failure. His blind ambition and thirst for public recognition placed him in political situations and power struggles which he predictably lost. Overall, Jeffrey Simon has put together a well-researched and comprehensive account of Flynn’s life, an account that has been overdue for 100 years.