The Strange Death of Dorothy Kilgallen (Part Three)

Content warning! This episode mentions sudden death, multiple suicides… and may have turned out to be one great big shaggy dog tale in itself. Reader discretion advised.


Hi all welcome back, let’s do part three of the Dorothy Kilgallen Tale. Parts one and two can be found on the links.

To state categorically John F Kennedy was not assassinated by some cabal, or some bigger power than Oswald, is a bit of a stretch. While the Warren Commission found no evidence of a conspiracy, the 1979 US House Select Committee on Assassinations stated their view a second shooter was involved. This conclusion rested largely on acoustic evidence that has been disproved in recent years as better acoustic modelling came along. The Assassination Records Review Board, tasked in the 1990s to preserve evidence, found inconsistencies which leave the door open to a conspiracy, most notably they claimed the photos of Kennedy’s brain were not the correct photos. They also question an inconsistency between the accepted story of Kennedy having been struck from behind, with eyewitness accounts which suggested a far bigger hole in the back of his head – suggesting a second shooter, in front of the president.

Conspiracy theorists often point to the number of people connected to the Kennedy assassination in some way, who died young, is on the high side – some theorists claiming as many as 104 suspicious deaths. This list includes people like
Mafia Don Sam Giancana, often implicated as a conspirator -gunned down in his apartment in 1966.
Lee Bowers – a witness who died in a car crash in 1966.
CIA agent Gary Underhill – an agent Jim Garrison claimed had information on the killing, who committed suicide in 1964.
FBI bigwig William Sullivan, who was accidentally shot while out hunting in 1972.
David Ferrie – a friend of Oswald’s who claimed not to know him, who was considered a possible co-conspirator by Garrison, and who also committed suicide in 1967.
George de Mohenschildt – a Russian American heavily questioned by the Warren Commission as a friend of Oswald’s, whose testimony helped link him back to the attempted assassination of General Edwin Walker. He committed suicide in 1977, after contacting George H.W Bush (a friend of a friend) to ask he call the CIA investigation into him off.

Two unusual deaths were Rose Cheramie, brought into hospital with minor injuries after being hit by a car. Rose claimed, two days before the assassination to have been travelling with two Italians who told her they were travelling to Dallas to kill the president. She would die in 1965, again struck by a vehicle. Joseph Milteer, a high ranking member of the Georgia KKK was secretly tape recorded 13 days before the assassination, claiming a hit was being prepared for the president. He would die in a freak heater explosion in 1974.

The magic of statistics shows a lot of the people who died on this list died of natural causes, some (i.e. mobsters) lived lifestyles that upped the risks of being murdered. When you adjust for everything else, the number is about what one can expect for the sample size, at that time.

I did have screeds of notes on motives – who would want JFK dead, and why. Last week, with news of the worst American president ever catching COVID, I redacted that section – not wanting to be accused of having an agenda in choosing this topic. For the record, I’m quite open about my disdain for Mr. Trump. I am erring on the side of caution however, dear reader you know the lore around this – a lot of people, on paper at least had a motive to conspire to kill Kennedy. Some had the wherewithal to hatch such a plot.

All this is to say, while I am disparaging of Dorothy Kilgallen’s findings, I personally believe there are enough inconsistencies to allow for any number of possible cabals to have taken Kennedy out. I will say Jim Garrison’s 1967 attempted prosecution of the businessman Clay Shaw – the only person to be tried for the murder of President Kennedy, seems baseless and quixotic to me. Oliver Stone’s film on Garrison’s quest, which hinted at a cabal made up of…. Well, pretty much everyone except Garrison himself seemed to get together to kill the president one afternoon – well, common sense tells you the more people involved, the higher the probability someone would have spilled the beans by now. To date, no-one of any substance has spilled the beans.
But, back to those deaths. Some were very strange. One in particular seemed to spook Dorothy.

Bill Hunter was far from a conspiracy theorist. The journalist from California went to Dallas to cover the killing, and subsequent investigation. He wrote a sixteen page special report on the assassination, “Three Days in Dallas”, where he concluded Oswald killed Kennedy, Ruby then killed Oswald. Hunter gave no indication of conspiracy at work. He enters the conspiracy as one of the 104. On 23rd April 1964, Hunter was hanging around the press room of the Long Beach police department, when he was accidentally killed by a police officer Creighton Wiggins. Initially claiming he’d accidentally dropped his handgun, which then discharged into Hunter, he changed his story to claim he was playing quick draw with another officer, Erroll Greenleaf. Greenleaf testified this was nonsense as he had his back to Wiggins at the time. When Hunter’s partner on the Dallas story, Jim Koethe, was murdered in a home invasion – the invader karate chopping him in the throat. A further air of mystery surrounded Hunter when Tom Howard – one of Jack Ruby’s attorneys, who let Hunter and Koethe into Ruby’s apartment – died aged only 48, of a heart attack. This led to Dorothy giving her friend Florence Pritchett-Smith (who initially introduced Dorothy to Kennedy) a copy of her manuscript of the chapter on the assassination, as insurance should she be accidentally shot by a dueling policeman too.


Which brings us back to the scene on the morning of 8th November 1965, what was so odd about Dorothy Kilgallen’s death?

First, let’s sketch the scene out again. If you recall, her hairdresser Marc Sinclaire arrived at 9am to find Dorothy was not yet up. When he checked her bedroom on the 5th floor – she was not there. Her body was found in the 3rd floor master bedroom. She was sitting up in bed in a blue robe Sinclaire had never seen before. Her makeup was still on. A decorative hairpiece was still in, as were her false eyelashes. If you recall episode one, Robert Ruark’s novel The Honey Badger was open beside her.
All of this was strange for a number of reasons.

First to the room, as discussed in an earlier episode, Dorothy and husband Richard Kollmar had an open marriage. The couple had all but split because Richard was foolish with Dorothy’s money, and slept around – some say a lot. Whether due to the lucrative nature of Dorothy and Richard’s morning radio show, or a concern for their reputation, or out of a desire to give their three children a normal upbringing – or Dorothy’s Catholicism making divorce very difficult – at some point both began living more or less separate lives, only giving the appearance of a loving relationship to the general public. One particular incident seemed to really upset Dorothy – finding Richard in bed with another woman in their 3rd floor master bedroom. Dorothy swore she would never sleep in that room again. Since that day she slept in a fifth floor room, Richard on the 4th floor.

Her appearance was rather unlike her also. That she wore a robe Sinclaire didn’t recognize could mean something – or she could have just bought a new robe. She was, however, meticulous about removing her makeup, hairpiece, and false eyelashes every night. The book also seemed odd. Robert Ruark’s posthumous final novel had been a big hit that year – Dorothy, a voracious reader, had already finished The Honey Badger months ago. What was really odd, however, Dorothy had exceedingly poor eyesight and could not read without her glasses. Her glasses were nowhere to be found. A light had been left on.

After some time the police arrived to examine the scene. Strangely, an officer had been parked outside the residence when Sinclaire arrived, but disappeared soon after. They would find no sign of foul play – no signs of a struggle, no bruising, cuts, or other marks. Her body would be transported to the coroner, not in her own borough of Manhattan, but Brooklyn – where a number of writers claim the office was infiltrated by the Mafia. They would find Dorothy had suffocated from a deadly mixture of barbiturates and alcohol – the same fate as Marilyn Monroe. A Dr. James Luke actually carried out the autopsy, however a Dr. De Meo, to Dr. Luke’s consternation ended up with their signature on the document. Samples of Dorothy’s fluids from her brain and stomach were kept, and examined decades later. when examined by modern machinery, the tests showed three different kinds of sleeping pills – and a dosage in the blood equivalent to between 15 and 20 pills in her body.

Though determined an accidental overdose, Dorothy’s death would be re-examined in 1966. After an 8 month investigation, the case was closed, having found no evidence of foul play.

A few other strange elements need to be discussed, however. First, the manuscript Dorothy was so concerned over – and all her notes concerning the Kennedy assassination – all disappeared in the course of the investigation. You recall Bill Hunter’s death prompted her to give a copy to her friend, writer and socialite Florence Pritchett-Smith? She died the following day, of a cerebral hemorrhage. Dorothy’s backup manuscript was never found among her belongings.

On the night before Dorothy’s funeral Dorothy’s friend and producer Bob Bach – the man you recall had drinks with her on the night she passed; the same man who dropped her off to meet the ‘mystery man’ – he sat with estranged husband Richard Kollmar. Asking Richard just what he made of the whole hullabaloo over Kennedy’s assassination, and Dorothy’s death – what had Dorothy found exactly? Kollmar replied “Robert, I’m afraid that will have to go to the grave with me.”

If this Tale feels a little cyclical – we’ve gone all around the world to find hints of a conspiracy, but nothing of substance, let me add to that feeling. I started this tale with a quote from Dorothy herself, about Marilyn Monroe. If you recall, Marilyn died under similar circumstances. Both ladies were insomniacs, and used sleeping pills. Both would become linked to John F Kennedy – though for very different reasons. Both deaths have been speculated over, writers asking did these ladies die because they knew too much? I personally have to say, I don’t know. I believe it possible they were murdered to protect the guilty. I believe it possible Kennedy was assassinated by a wider conspiracy, though it is more probable Oswald acted alone. I’m a firm believer extraordinary claims need extraordinary evidence to move from possible to probable… but in Dorothy’s case one piece of evidence does speak to me a little louder than the others – the light.
She wrote of Marilyn “If she was just trying to get to sleep, and took the overdose of pills accidentally, why was the light on? Usually people sleep better in the dark” While this may have been the case for Marilyn, it certainly was for Dorothy – it represents her actively reflecting on her own needs when drifting off to sleep. Take your pills, turn off the light, wait for the pills to kick in. I’m unconvinced she found anything of note on her friend the president, but I feel it highly likely she was murdered for things others believed she knew.

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