Prohibition made “Lucky” Luciano the richest and most powerful organized crime boss in the country—but his chokehold over New York City’s prostitution industry would ultimately bring him down.

He had managed to escape prosecution for mob-related murders that had made him the reigning boss in the late 1920s and 1930s, but in 1936, Thomas Dewey, then a federally-appointed special prosecutor for Manhattan, and his team of investigators and lawyers developed what would become a sensational prostitution case that riveted the city.

Investigators conducted simultaneous raids on some 40 brothels and eventually built a case against him using about three-dozen witnesses, including a slew of prostitutes and madams. The key witness was a prostitute named Florence “Cokey Flo” Brown, a hard-bitten heroin addict who testified that Luciano told her he wanted to run his string of bordellos like a chain-store operation.

Amazingly, Luciano took the witness stand, confident he could charm the jury. It didn’t work; he was convicted on 60 counts of compulsory prostitution and sentenced to 30 to 50 years in prison. 

He likely would have died in prison, but he cooperated with the war effort in 1942 after the sinking of the SS Normandie on the Brooklyn waterfront raised fears of sabotage and longshoremen threatened to strike. After becoming Governor of New York, Dewey commuted Luciano’s sentence on the proviso that he be deported to Italy, where he died in 1962. While in Italy, he continued to coordinate with fellow mobsters on international drug trafficking.

Prostitution burst back into the headlines in 1967, with a dramatic two-part series in the New York Times, contained in the Municipal Library files. The first story quoted Alfred Scotti, the head of the Rackets Bureau in the Manhattan district attorney’s office, as saying the mob pulled back on prostitution after Luciano’s conviction. 

 “It’s too difficult to organize and the mobsters find gambling, narcotics—and for that matter many legal operations—much more profitable.”

The two-month Times investigation found that some East Side bars allowed hookers to “operate surprisingly openly,” although the woman often had to convince her customer to buy three drinks before leaving.

The Times series prompted the State Assembly to toughen prostitution laws over the objections of some, like then-Assembly member Charles Rangel, who wanted to decriminalize it. “Prostitution is a problem that will be with us as long as we are a legislative body,” he said.

As the city began its slide toward an ugly, wide-open Times Square—as later depicted in movies like Taxi Driver and the television series The Deuce—an NYPD press release in the archives dated February 1970 said prostitution arrests had increased 13 percent from 1968 to 1969.  

Public pressure pushed the Lindsay administration to crack down on prostitution. On July 2, 1971, Mayor Lindsay’s criminal justice coordinator reported on a meeting with representatives of District Attorney Frank Hogan and said prosecutors vowed to “push harder” and seek jail terms for repeat offenders and bail jumpers. A week later, a memo from Lindsay’s counsel’s office suggested a broad crackdown on pimps.

A January 1973 report on the “Status of Enforcement Programs to Control Prostitution and Pornography in the Midtown Area" warned of the deterioration of Times Square.

“For a considerable period of time, the Midtown area, and particularly Times Square, has witnessed a thriving business in prostitution and pornography,” the report said. “These vices do not exist in a vacuum. On the contrary, they prosper in a milieu of thieves, degenerates and undesirables.”

It noted that the NYPD’s Manhattan South Morals District made 1,031 prostitution arrests between April and November of 1972, but that just 92 resulted in jail time, while 396 cases generated fines. There was also some violence when three cops were injured in a melee with hookers resisting arrest; one pimp was arrested for trying to stab a cop.

The report listed 30 hotels that “catered to” prostitution, including The Sun, at 606 Eighth Avenue listed then as owned by the “Trump Realty Corp.” The city secured restraining orders against six of the hotels. Three of them, The Raymona, The Radio Center and the Lark, soon closed. The report noted that The Sun was “cooperating” with authorities to clean up the hotel.

It also listed 41 massage parlors involved in prostitution and six midtown bars as “havens for pimps,” and noted that the random arrest and conviction approach “has not achieved the hoped-for success." The city then tried another tactic: It subpoenaed the tax records of 13 pimps to determine if tax evasion charges were an option and also formed a multi-agency task force to inspect and possibly shut down massage parlors.

That brought mixed results, at best. In 1976 Mayor Abe Beame created the federally-funded Midtown Enforcement Project (MEP) to clean up Times Square. One tactic was to put together a team of investigators from the city’s Health, Buildings and Fire departments to shut the parlors down for various violations.

In one of its first reports for the period of April to June of 1977, officials reported about 200 arrests for prostitution and obscenity, including live sex shows. From January 1 to March 31 of 1977, the NYPD’s Public Morals Squad made a total of 850 prostitution arrests, most of which resulted in some jail time. And a zoning change in the late 1970s “effectively banned most massage parlors.”

The most disturbing part in this period was a spike in juvenile prostitution, primarily in the Times Square area, as noted in a MEP report on juvenile prostitution from the Criminal Justice Center of John Jay College.

The report, which drew on 3½ months of data and interviews with 32 teenage girls, found it was hard to dissuade girls from that life.

“It is quite daunting to consider methods to persuade a 15-year-year-old who is earning $150 a night, seven days a week, that she should return to her vocational high school,” the report said, adding that the girls they interviewed came from every part of the country and that most said girls that they knew brought them into the life.

It told of Debbie, 15, from upstate New York who came to the City to visit a friend and found the friend was living with a “friendly charming man who bought and gave her clothes” and persuaded her to become a prostitute. Debbie told the interviewer the pimp thwarted her attempts to go back home.

The report also cited Kathy, 17, from Westchester County, who struck up a friendship with a girl on a visit to New York City. They stayed in touch, and after a while, the girl convinced Kathy to become a prostitute.

“None of the girls claimed they were kidnapped or raped and then ‘turned out’ as prostitutes.”

The problem continued to worsen, though. In July, 1978, it was estimated that Times Square had 52 adult movie houses with live sex and peep shows, 63 massage parlors and 34 “prostitution-prone” hotels.

In August, 1978, the first of two Times Square “Action Plans” declared that: “Over the past four decades, successive city administrations have made repeated attempts to ‘clean up’ Times Square.”

Part of the plan was the creation of bi-weekly Midtown Task Force meetings at City Hall. The report noted that the city launched Operation Crossroads earlier in the year, which included increased police visibility and foot patrols in the area from 40th to 50th Streets between Sixth and Ninth Avenues. The NYPD also began a crackdown on “johns” carried out by undercover female police officers.

But news reports of the increasing problem angered Mayor Koch, who sent a stern memo to Deputy Mayor Nat Leventhal on May 20, 1982, in which he called for a “campaign to deal with child prostitution” in Midtown.

“Enclosed is a copy of a report that I received from (Police Commissioner) Bob McGuire,” Koch wrote. “From my point of view, it is unsatisfactory. They believe they are doing all that can be done and that they are limited by laws in making inquiries when they see a suspicious adult with a child. We know that many of these situations involved adult pickups of children who may want to be picked up for prostitution purposes; nevertheless, they must be protected.”

Koch ordered Leventhal to convene a meeting “with the appropriate people to figure out a strategy to deal with this problem.” Attached to the letter was report from the U.S. General Accounting Office, which said child prostitution had increased in the last five years and that as many as 400 to 500 minors were working as prostitutes on any given day.

The various strategies made a dent in teen prostitution, at least in Midtown.  A second Times Square Action Plan, issued in October 1984, noted an increase in “quality hotels” in the area. It also said there had been a decrease in “sex-related” business in Times Square from 96 in December 1977, to 51 in September 1984.

By the early 1990s and beyond, Times Square was largely transformed from a hotbed of prostitution to a tourist-friendly area, with rejuvenated hotels, Disney Stores and Mickey Mouse largely replacing streetwalkers.

But of course, prostitution didn’t go away. A Daily News story in the files from March 1981 was headlined: “Thy Neighbor’s Vice, a Tour of the Thriving Brothels of Manhattan.” It reported that brothels were alive and well between East 14th St. to Times Square and in parts of the Upper East Side and Upper West Side.

In 1986, a State Bar Association committee suggested creating “commercial districts” where prostitutes could work. That didn’t go anywhere, nor did a bill introduced in the State Senate this summer which called for the decriminalization of prostitution.

As Charlie Rangel said many years ago, prostitution will always be with us.