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Isidor “Izzy” Einstein and Moe Smith were two middle-aged men from New York’s Lower East Side who managed to arrest 4,932 offenders, haul in roughly five million bottles of illegal liquor, and sport a conviction rate of 95 percent from 1920–25. Before becoming the premier booze detectives of their day, the Austrian immigrant Einstein had been a street peddler and a postal clerk, while Smith had owned a cigar store. When the duo first applied to work for the Prohibition Bureau for $40 a week, the G-men in charge weren’t overly impressed. Somehow, Einstein and Smith managed to convince their superiors by selling them on the idea that hoodlums would never suspect two portly, regular-looking guys of being undercover agents. Einstein and Smith, like Sherlock Holmes before them, gained a reputation for being excellent at concocting disguises that actually worked. Sometimes, the pair got away with hiding in plain sight, even though most speakeasies had their pictures hanging on the wall. Ultimately, it wasn’t the criminals who sank the careers of Izzy and Moe, but their own fellow agents, who grew increasingly jealous of the pair’s success. Unlike fictional detectives, Einstein and Smith weren’t neurotic geniuses who relied on their vast wealth of knowledge. For the most part, the pair became successful detectives because of their willingness to work long hours and their native knowledge of New York City life. Einstein was also gifted with languages—when need be, he could converse with suspects and witnesses in Yiddish, German, Polish, Hungarian, and even Chinese.

When your name gets mentioned as the possible inspiration behind both Inspector Harry Callahan of Dirty Harry fame and Steve McQueen’s turn as Lieutenant Frank Bullitt in 1968’s Bullitt, you know you’re cool. The man who can make that claim is Dave Toschi, who served as an inspector in the San Francisco Police Department from 1952–83. During Toschi’s time in San Francisco, he was known for dressing well, being meticulous, wearing his gun in a trademark quick-draw holster, and constantly munching on animal crackers. He was also known as one of the primary detectives involved in the still-unsolved Zodiac case.From December 1968 until October 1969, the Zodiac Killer terrorized San Francisco and the surrounding Bay Area with a string of grisly murders. Worse still, the killer taunted and tormented the police and public alike with bizarre letters or ciphers and several threats concerning acts of terrorism that would target schoolchildren. For his part, Toschi, along with other members of the San Francisco PD, relentlessly hunted the killer for years, although their efforts were never rewarded with a conviction. The closest Toschi came to catching Zodiac was the investigation of Arthur Leigh Allen, whom Toschi has called “the best suspect” in the entire case.While Toschi is mostly famous for his role in the Zodiac case , he was also involved in investigating the Zebra murders, a series of racially motivated murders and attacks committed by a black nationalist gang against random whites during the mid-1970s.

Often called the “Broadway Cop,” Johnny Broderick patrolled New York’s theater district as a member of the New York Police Department from 1923–47. In his time, Broderick was known throughout the city as a cop not to be messed with. His reputation was mostly built around his willingness to beat up gangsters and suspects alike, and many stories about “Broadway Johnny” portray him as a larger-than-life tough guy who could easily lick the hard-boiled detectives created by writers like Dashiell Hammett and Raymond Chandler.
Born into an Irish-American family in Manhattan’s Gashouse District, Broderick came home after serving in the Navy during World War I and became a “labor slugger.” He also served as the bodyguard for Samuel Gompers, the founder of the American Federation of Labor. Then, after a brief turn as a firefighter, Broderick became a patrolman in 1923. During his time on the force, Broderick beat up the legendary New York gangster Jack “Legs” Diamond and dumped him into a garbage can, and he also performed bodyguard work for the heavyweight boxing champion Jack Dempsey.
Besides his beating of “Legs” Diamond, Broderick was also famous for squaring off against armed prisoners in New York’s infamous Manhattan Detention Complex, better known as The Tombs. When the prisoners barricaded themselves behind a coal pile in a last-ditch effort to fend off a police counterattack, Broderick rushed them and began firing at the would-be escapees. Broderick’s brazen attack may have been the thing that finallydrove the criminals to commit suicide.
Although loved by a large portion of the New York public for his willingness to tackle crime head-on, Broderick was loathed by many politicians and was the frequent target of civil cases that accused him of misconduct and police brutality.