Though Dorothy Kilgallen isn't a familiar name to many people today, there was a time — from the 1940s to the mid-1960s — when she was one of the biggest stars in the media world, a trailblazing woman journalist and TV personality who paved the way for generations to follow.
As a syndicated columnist in more than 200 newspapers across the nation, Kilgallen covered everything from entertainment and politics to crime. When she wasn't covering big stories such as the 1954 murder trial of Dr. Sam Sheppard (the inspiration for the TV series and movie "The Fugitive") or Soviet leader Nikita Khrushchev's visit to the U.S. in 1959, she was arousing the ire of Frank Sinatra by reporting on his personal life. (According to Sinatra biographer James Kaplan, the singer and actor was so irked by what Kilgallen wrote about him that he once sent her a tombstone with her name carved on it.) She also appeared on Americans' TV screens each week as a panelist in the popular quiz program "What's My Line?"
But Kilgallen never got a chance to finish what might have been her biggest story — her investigation into the assassination of President John F. Kennedy, and the suspicion that alleged assassin Lee Harvey Oswald's subsequent murder by Dallas nightclub owner Jack Ruby while in police custody might have been part of a coverup of a bigger plot. Instead, on Nov. 8, 1965, Kilgallen was found dead in her New York City townhouse, in what the medical examiner decided was possibly an accidental overdose of alcohol and barbiturates, according to this 1965 United Press International story.
More than a half-century later, that explanation is challenged by Mark Shaw, a former criminal defense attorney and legal analyst for CNN and other media outlets, and the author of more than 20 books. He's spent years investigating the circumstances of her death, and believes that Kilgallen actually was murdered, in order to prevent her from uncovering the truth about what had happened in Dallas.
"She knew it wasn't Oswald alone," Shaw explains.
Shaw has written extensively about Kilgallen, including a 2016 biography, "The Reporter Who Knew Too Much: The Mysterious Death of 'What's My Line' TV Star and Media Icon Dorothy Kilgallen," and a 2021 follow-up, "Collateral Damage: The Mysterious Deaths of Marilyn Monroe, Dorothy Kilgallen and the Ties That Bind Them to Robert Kennedy and the JFK Assassination." The movie rights to "Collateral Damage" recently were optioned by a production company connected to actor Mark Wahlberg, according to Deadline.)
Who Was Dorothy Kilgallen?
Born in Chicago in 1913, Kilgallen was the daughter of Jim Kilgallen, a newspaper and wire service reporter. At a young age, she decided to follow in her father's footsteps. After she briefly attended the College of New Rochelle, her father managed to get her a two-week tryout at the New York Evening Journal, according to Shaw's 2016 biography. She quickly became a star reporter in her own right, so adept at covering court cases that in 1935, she was assigned to cover the trial of Bruno Hauptmann, accused of kidnapping and killing the son of aviator Charles Lindbergh.
After her bosses promoted her from reporter to columnist, Kilgallen made a name for herself as one of three New York journalists competing in a race around the world. She finished second, making the journey in 24 days, 13 hours and 51 minutes, and published a book about her adventure, "Girl Around the World," which was made into a 1937 Hollywood film, "Fly Away Baby."
After the Evening Journal merged with the New York American in 1938, the new Journal-American appointed Kilgallen as its Broadway columnist, making her "the first woman in a hitherto masculine field," as her Associated Press obituary eventually would note.
Like today's media superstars, Kilgallen worked in multiple platforms. She soon began doing a radio program as well. She married actor turned theatrical producer Dick Kollmar, and found time to raise three children.
By the 1950s, she also was a regular panelist on the TV program "What's My Line?," where she guessed the occupations of guests and the identity of mystery celebrities. (In this YouTube video of a 1965 episode, a blindfolded Kilgallen tries to guess the identity of Sean Connery.) Kilgallen was such a celebrity in her own right that Edward R. Murrow interviewed the columnist from her home in New York.
Kilgallen was Barbara Walters and Oprah Winfrey rolled into one, Shaw says. "Nobody's ever had a journalistic career like Dorothy had, as well as her television career," he notes.
Kilgallen and the Kennedy Assassination
But fame didn't stop Kilgallen from continuing to be a hard-driven reporter. After the assassination of President Kennedy, with whom she had become friends, the columnist wasn't satisfied with the official version of his assassination and the aftermath. In particular, she was suspicious about the killing of accused assassin Oswald by Ruby in the basement of Dallas police headquarters, two days after JFK's murder.
"Well, I'd like to know how, in a big, smart town like Dallas, a man like Jack Ruby — owner of a strip tease honky tonk — can stroll in and out of police headquarters as if it was at a health club at a time when a small army of law enforcers is keeping a 'tight security guard' on Oswald," Kilgallen wrote in a column published a week after JFK's death.
According to Shaw's 2016 biography, Kilgallen began probing the Dallas police and FBI investigations, and built a growing file of information about Oswald and Ruby from her contacts in Dallas, in an effort to make sure Americans got the whole story of what had happened. She grew even more suspicious when she learned that San Francisco attorney Melvin Belli, primarily a civil litigator — his 1996 obituary called him "the King of Torts" – would be representing Ruby. Belli hadn't tried a murder case in years, which made him seem like an unusual choice. And as Shaw notes, the flamboyant lawyer's clients included prominent mobster Mickey Cohen, a connection that would later seem troubling to those who suspected organized crime involvement in JFK's murder.
Shaw, who also has written a 2011 biography of Belli, notes that Belli chose to put on an unorthodox insanity defense for Ruby, claiming that a rare form of epilepsy had rendered the nightclub owner incapable of knowing right from wrong when he shot Oswald. It was a theory "which I didn't understand, and neither did the jury," Shaw notes.
When Ruby went on trial in Dallas in February 1964, Kilgallen was in attendance. She had dinner with Belli and asked for an interview with his client. The lawyer told her it wasn't possible. But Kilgallen persisted, and eventually circumvented Belli by going through his co-counsel, Joe Tonahill, according to Shaw's biography.
"She landed the interview," Shaw says. "She was the only reporter out of 400 there who interviewed Jack Ruby."
As Kilgallen recounted in an exclusive for the Journal-American, the defendant had a trembling handshake, "like the heartbeat of a bird," and seemed unnerved. "I feel I'm on the verge of something I don't understand — the breaking point maybe," she quoted him as saying. Later in the trial, Kilgallen spoke to Ruby a second time, but didn't write a column about it, instead keeping the substance secret, according to Shaw's biography.
After Ruby's conviction, Kilgallen continued to dig into the case, convinced that the whole truth hadn't been told. She obtained from a source a copy of Ruby's secret testimony to the Warren Commission. In her August 1964 exclusive, she revealed that Ruby told Chief Justice Earl Warren that he believed JFK's assassination had been the result of a plot, but insisted that he hadn't been involved. He also told Warren that the official investigation was "a lost cause," Kilgallen reported. (In 1966, Ruby's conviction was overturned by an appeals court, which found that the trial judge had allowed inadmissible testimony and should have granted a change of venue, but Ruby died of cancer before he could be retried.
But Kilgallen wasn't through investigating. In a September 1965 column, she wrote that the story of Oswald and the assassination "isn't going to die as long as there's a real reporter alive — and there are a lot of them alive."
The following month, according to Shaw's biography, Kilgallen traveled to New Orleans — a hint that she may have been investigating organized crime involvement in the JFK assassination.
"She didn't go to Washington, D.C., to look into the military-industrial complex, or stay in Dallas and look at Lyndon Johnson, or go to Miami looking at these Cuban exiles," Shaw says. He believes that Ruby had told Kilgallen that he was connected to Louisiana mob boss Carlos Marcello, and that at his behest, Ruby had killed Oswald — "to build the wall, to silence him," Shaw explains.
Marcello had reasons to be angry at the Kennedy administration, after he was deported to Guatemala in 1961 and subsequently prosecuted in federal court on immigration-related charges (though he was acquitted on the same day that JFK was killed). A U.S. House committee reinvestigating the JFK assassination in 1979 concluded that Marcello "had the motive, means and opportunity to have President John F. Kennedy assassinated, though it was unable to establish direct evidence of Marcello's complicity."
Kilgallen Is Found Dead
But if Kilgallen was onto something, she didn't have the time to pursue it further. On Nov. 8, 1965, her body was found — newspaper accounts differ about whether it was by a maid or her hairdresser, Marc Sinclaire – in her New York City home. But Shaw says there were plenty of details that should have been a tipoff that something was amiss.
"She was found in her townhouse in a bedroom she never slept in," Shaw says. "The columnist also was wearing makeup, false eyelashes and a hairpiece, and a robe instead of the pajamas that she normally wore to bed. There was a book upside down in her lap that she'd already read, and her reading glasses weren't around."
"Obviously, to anybody with a brain, that's a staged death scene," Shaw continues. "But the police came, they found an empty bottle of Seconal sleeping pills and right away, okay, this is another celebrity who overdosed on drugs."
As detailed in "The Reporter Who Knew Too Much," other troubling details are evident in the medical examiner's report on Kilgallen's death, including the presence of Tuinal, a powerful sedative-hypnotic medication that she hadn't been prescribed by her doctor.
And then there were the missing files and notes from her investigation into Jack Ruby, the mob and the Kennedy assassination. Hairdresser Marc Sinclaire later recalled that he saw Kilgallen carrying around "a big packet of papers with her that she said pertained to the assassination." The file mysteriously went missing after Kilgallen's death and has never been found, according to Shaw's biography.
In addition to halting her investigation, the assumption that Kilgallen had died of a drug-and-alcohol overdose "destroyed Dorothy Kilgallen's reputation," Shaw laments. As a result, he says, "She basically disappeared from the face of the earth."
Shaw's biography of Kilgallen and subsequent work about her has helped to revive interest in the pioneering woman journalist, and he's determined to keep alive the memory of "one of the greatest reporters who ever lived." He corresponds with new admirers of her work, including students inspired to study journalism by her example. "Two guys that email me all the time — they go to Dorothy's burial site and lay flowers there," he says.
More than a half-century after Kilgallen's death, "she's getting that respect back," Shaw says.
Dorothy Kilgallen was 52 years old when she died. Here, her fellow panelists on "What's My Line?" say goodbye: