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July 27, 2026 13 mins

In the mid-1900s, Dorothy Kilgallen was a famous journalist and popular media personality -- but her investigation into the deaths of President Kennedy and his assassin, Lee Harvey Oswald, may have gotten her killed, too. Learn about the alledged organized crime coverup Kilgallen was looking into in today's episode of BrainStuff, based on this article: https://history.howstuffworks.com/historical-figures/dorothy-kilgallen.htm

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Speaker 1 (00:01):
Welcome to Brainstuff, a production of iHeartRadio. Hey Brainstuff, Lauren
Bogelbaum here. Though Dorothy Kilgallen is not a name familiar
to many people today, there was a time from the
nineteen forties to the mid sixties when she was one
of the biggest stars in the media world, a trailblazing

(00:23):
journalist and TV personality who paved the way for generations
to follow. As a syndicated columnist in more than two
hundred newspapers across the United States, Kilgallen covered everything from
entertainment to politics to crime. When she wasn't following big
stories like the nineteen fifty four murder trial of doctor

(00:44):
Sam Shepherd, which was the inspiration for the movie The Fugitive,
or Soviet leader Nikita Khrushchev's visit to the US in
nineteen fifty nine, she was arousing the ire of Frank
Sinatra by reporting on his personal life. According to Sinatra
biographer Sames Kaplan, the singer and actor was so irked
by what kill Gallen wrote about him that he once

(01:05):
sent her a tombstone with her name carved on it.
She also appeared on American's TV screens every week as
a panelist on 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 in Dallas, including her suspicion

(01:28):
that alleged assassin Lee Harvey Oswald's subsequent murder while in
police custody might have been part of a cover up
of a bigger plot. Instead, on November eighth of nineteen
sixty five, Kilgallen was found dead in her New York
City townhouse in what the medical examiner decided was possibly
an accidental overdose of alcohol and barbituates. Over sixty years later,

(01:52):
that explanation is being challenged by one Mark Shaw, a
former criminal defense attorney and legal analyst for CNN and
media outlets. He's spent years investigating the circumstances of her
death and believes that kill Gallen was actually murdered to
prevent her from uncovering the truth about what had happened
in Dallas. When how Stuff Works spoke with Shaw for

(02:15):
the article this episode is based on, he said she
knew it wasn't Oswald alone. Shaw has written extensively about
kill Gallen, including four books, starting with the best selling
twenty sixteen biography The Reporter Who Knew Too Much. This
Cold Case is clearly still sparking interest. His books have
been optioned for potential documentary films. Today, let's talk about

(02:39):
who kill Gallen was and what we can make of
her death today. Born in Chicago in nineteen thirteen, Kill
Gallen was the daughter of 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

(03:01):
at the New York Evening Journal. She quickly became a
star reporter in her own right, so adept at covering
court cases that in nineteen thirty five, she was assigned
to cover the Lindberg baby kidnapping trial. After her bosses
promoted her from reporter to columnist. Kilgallen made a name
for herself as one of three New York journalists competing

(03:21):
in a race around the world. She finished second, making
the journey in twenty four days, thirteen hours, and fifty
one minutes, and published a book about her adventure, Girl
Around the World, which was made into the nineteen thirty
seven Hollywood film Flyaway Baby. After The Evening Journal merged
with The New York American in nineteen thirty eight, the

(03:41):
New Journal American appointed Kilgallen as its Broadway columnist, making
her the first woman in a hitherto masculine field, as
her associated pres obituary would eventually note. She married actor
turned theatrical producer Dick Calmar, and they found time to
raise three children Togetherlike today's media superstars, kill Gallen worked

(04:03):
in multiple platforms. She began doing a radio program during
World War Two, and by the nineteen fifties she was
a regular panelist on the TV show What's My Line,
where she guessed the occupations of guests and the identity
of mystery celebrities. Shaw describes kill Gallen as Barbara Walters
and Oprah Winfrey rolled into one, a quote nobody's ever

(04:26):
had a journalistic career like Dorothy had, as well as
her television career. But fame didn't stop kill Gallen from
continuing to be a hard driven reporter. After the nineteen
sixty three assassination of President Kennedy, with whom she had
become friends, the columnist wasn't satisfied with the official version

(04:47):
of his assassination and the aftermath. In particular, she was
suspicious about the killing of accused assassin Oswald by local
nightclub owner Jack Ruby in the basement of the Dallas
Police headquarters two days after JFK's murder. Kilgallen wrote in
a column published a week after JFK's death, Well, I'd

(05:07):
like to know how in a big, smart town like Dallas,
a man like Jack Ruby, owner of a strip teas
honky tonk, can stroll in an 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 began probing the

(05:27):
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 that the public
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, would be representing Ruby.

(05:50):
Bell I hadn't tried a murder case in years, which
made him seem an unusual choice, and Belli's clients included
prominent mobster Mickey Cohen, a connection that would later seem
troubling to those who suspected the involvement of organized crime.
In JFK's MURTYR Shaw, who also published a biography of
Belly in twenty eleven, notes that Belly chose to use

(06:13):
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 Osbald. It was
a theory, Shaw notes which I didn't understand, and neither
did the jury. When Ruby went on trial in Dallas
in February of nineteen sixty four, kill Gallen was in attendance.

(06:36):
She had dinner with Belly and asked for an interview
with his client. The lawyer told her it wasn't possible,
but kill Gallen persisted and eventually circumvented Belly by going
through his co counsul Shaw said she landed the interview.
She was the only reporter out of four hundred there
who interviewed Jack Ruby. As kill Gallen recounted an exclusive

(07:00):
for the journal American the defendant had a trembling handshake
quote like the heartbeat of a bird, and he seemed unnerved,
like he was at his breaking point. Later in the trial,
kill Gallen spoke to Ruby a second time, but didn't
write a column about it, instead keeping the substance secret.
After Ruby's conviction, kill Gallen continued to dig into the case.

(07:23):
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 nineteen sixty four exclusive,
she revealed that Ruby told Chief Justice Earl Warren that
he believed JFK's assassination had been the result of a plot,
and insisted that he hadn't been involved. He also told

(07:46):
Warren that the official investigation was quote a lost cause.
Kill Gallen reported. In nineteen sixty six, 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. Still, Kilgallen was not through investigating. In

(08:10):
a column in September of nineteen sixty five, she wrote
that the story of Oswald and the assassination quote 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,
Kilgallen traveled to New Orleans, a hint that she may
have been investigating the potential organized crime involvement in the

(08:32):
JFK assassination. Shaw explained 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 believes that Ruby told
Kilgallen he was connected to a Louisiana mob boss by

(08:52):
the name of Carlos Marcello, and that at his behest,
Ruby had killed Oswald to silence him. Marcello had reasons
to be angry at the Kennedy administration after he was
deported to Guatemala in nineteen sixty one and subsequently prosecuted
in federal court on immigration related charges, though he was
acquitted on the same day that JFK was killed. A

(09:15):
US House committee reinvestigating the JFK assassination in nineteen seventy
nine concluded that Marcello quote 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, but
if Kilgallen was on to something, she didn't have the

(09:36):
time to pursue it further. On November eighth of nineteen
sixty five, when Kilgallen was only fifty two years old,
her body was found in her New York City home.
Newspaper accounts differ about whether it was by a maid
or her hair dresser, but Shaw says there were plenty
of details that should have been a tip off that

(09:56):
something was a miss. Shaw said she was found in
her townhouse, in a bedroom she never slept in. The
columnist was also wearing makeup, false eyelashes, and a hair
piece and a robe instead of the pajamas that she
normally wore to bed. There was a book upside down
in her lap that she had already read, and her
reading glasses weren't around. Obviously, to anybody with a brain,

(10:19):
that's a staged death scene. But the police came. They
found an empty bottle of second all sleeping pills, and
right away, okay, this is another celebrity who overdosed on drugs,
and other troubling details were evident in the medical examiner's
report on Kilgallan's death, including the presidence of too and All,

(10:40):
a powerful sleeping pill 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. Her hairdresser, Mark Sainclair later recalled that
he saw kill Gallen carrying around quote a big packet
of papers with her that she said pertained to the assassination.

(11:03):
The file mysteriously went missing after kill Gallan's death and
has never been found. In addition to halting her investigation,
the assumption that kill Gallen had died of a drug
and alcohol overdose destroyed her reputation in some circles and
made the public more or less forget her. Shaw's biography
and other work about kill Gallen has helped revive interest

(11:26):
in this pioneering woman journalist. He wrote three follow ups
in twenty eighteen, twenty twenty one, and twenty twenty five,
a titled Denial of Justice, Collateral Damage, and Abuse of Power,
each connecting more points in kill Gallen's story in JFK's
assassination to the mysterious deaths of other figures like Robert F.
Kennedy and Marilyn Monroe, and as more evidence has come

(11:50):
to life connecting the credible involvement of Marcello. Under J.
Edgar Hoover's protection, A, Shaw is determined to keep alive
the memory of quote one of the greatest reporters who
ever lived. He corresponds with the new admirers of her work,
including students inspired to study journalism by her example. Shaw's

(12:13):
books also inspired the New York City Council to co
name a Manhattan street after her. On November eighth of
twenty twenty five, on the sixtieth anniversary of her death,
the corner of Park Avenue and East sixty eighth became
Dorothy Kilgallen Way, six decades after Killgallan's death, Shaw said
she's getting that respect back. If you're interested in learning more,

(12:37):
you can check out Shaw's website, the Dorothy Kilgallenstory dot org.
Kilgallen is spelled kilga l l e n. It contains
samples of Killgallen's work, including her columns on the Jack
Ruby trial. Not a sponsor just a fun resource if
you're into true crime. Today's episode is based on the

(13:01):
article did journalist Dorothy Kilgallen's probe of JFK's assassination lead
to her death? On how stuffworks dot Com? Written by
Patrick J. Kider. Brain Stuff is production of iHeartRadio in
partnership with HowStuffWorks dot Com and is produced by Tyler Klang.
Four more podcasts from iHeartRadio, visit the iHeartRadio app Apple
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