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Jack Ruby: The Many Faces of Oswald’s Assassin

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Many factors at work in the genesis of today’s post. 1) The recent release of what are the purported last remaining “JFK files” by the Trump administration; 2) Today is the most commonly given date for the birth of Jack Ruby (Jacob Rubenstein, 1911-1967), although birth records were not kept in Chicago at the time, and as many as 6 different dates have been given. If Ruby was born today, then he was born on the same day as the Triangle Shirtwaist Factory Fire, a day on which many Jews died; and 3) My new friend Danny Fingeroth just wrote a book about this topic, called Jack Ruby: The Many Faces of Oswald’s Assassin. Fingeroth is best known as a biographer of Stan Lee, and a comic book writer himself. Ya wanna know something strange? Stan Lee’s cousin Mel Stuart directed the TV movies Ruby and Oswald (1978) AND The Triangle factory Fire Scandal (1979), thus proving what I have always known — the Kennedy assassination was a conspiracy spearheaded by Marvel Comics, and it goes back to 1911!

I honestly can’t say how long it might have taken me to get around to the topic of Jack Ruby if not for Danny’s book, but it’s probable I would have eventually. Not because of the true crime element, although I do write about true crime from time to time, but because of the show biz factor (and indeed most of the true crime I write about does have show business as a factor). Prior to his eternal infamy earned by the confusion he caused in murdering Lee Harvey Oswald two days after Kennedy’s assassination, Ruby was widely known around Dallas as a local character. Even if neither Oswald nor Ruby had played any direct role in the events of November 1963, and someone else had done the job, it’s likely that those two men would be mentioned as footnotes in any thorough book about the topic. Ruby was best known prior to this as the owner and manager of many strip joints, nights clubs and bars. And that’s the angle that could conceivably rate him at least a mention no matter WHAT happened in this cock-eyed clown car crack-up. Like, he employed performers that I have written about previously, such as burlesque dancer Candy Barr, ventriloquist Bill DeMar, and then-aspiring comic Gabe Kaplan. (That is how I came to meet Danny; it was through his auspices that Kaplan made an appearance at Marx Fest last year. Fingeroth met Kaplan at a book event (for this book), and of course Kaplan, best known from his sit-com Welcome Back, Kotter, also played Groucho Marx on many occasions over the years).

I should hasten to point out that Fingeroth is not a conspiracy theorist. He hits the sweet spot, in my opinion. He mentions the questions some people have, but is non-committal about following anyone down that road. While not putting anyone down, he presents a lot of information that allows us to come to our own conclusion — that Ruby acted alone. I understand the temptation to think otherwise, especially if you lived through the event. I was born two years later — in fact, I was born on the very day that columnist Dorothy Kilgallen, who claimed many times to have the goods on Ruby and Oswald, was found dead in her hotel room of an O.D. of booze and barbiturates, just like Marilyn Monroe. (Quite true! You can look it up — and not just on Travalanche). Kilgallen was a panelist on What’s My Line? which was hosted by John Daly, who happened to be Chief Justice Earl Warren’s son-in-law, and some think this was her line to the truth. Then she had the deceptive acumen to die on the very day I was born. Thus it is I, the reincarnated spirit of Dorothy Kilgallen, who arrives to tell you the TRUE story of Jack Ruby today, through the magic of Danny Fingeroth and The Mystic Eye of Agamotto!

Back to the plane of reality — somewhat. You may wonder, why on earth would anyone be interested in the life of Jack Ruby, apart from those who are obsessed with Ruby, Oswald, Kennedy and a thousand other players in this never-ending role-play game of Dungeons and Dallas? Well, I absolutely was, and the book rewards such curiosity, because Ruby was not only a fascinating character but he lived a colorful, and, dare I say, entertaining, life.

Here’s another fascinating coincidence, and I’m sure it’s just a coincidence. The other book I’m reading at the moment is Robert Bader’s Zeppo: The Reluctant Marx Brother, and believe it or not there is a STRONG correspondence between the lives of the two men. Both were Jewish guys who ran with youth gangs on the streets of Chicago, committing also sorts of low level criminal shenanigans: thefts, burglaries, hustles, cons, street fights. Both could best be described as “criminal associates”. And frankly, I’m not sure I’ve ever heard of ANYONE in the night club business who couldn’t be described as a “criminal associate”. That one’s not prejudice, that’s just being alive on planet earth. You traffic in booze, gambling, women, and muscle, and you’re a straight arrow? The more I become immersed in show business back in the day, the more I realize that it’s like that, a large proportion of your favorite entertainers have hobnobbed with crooks, that’s just how it is. I can’t see how they could avoid it. Including, haha, Zeppo Marx! So I think we can add Big Joe Helton and Alkie Briggs to our list of conspirators!

Ruby had his redeeming qualities. In fact, one of them might be called his tragic flaw, that literary device wherein a hero’s virtue overtips the balance and finds his own doom. The virtue? He wouldn’t sit still for Anti-Semitism. He literally was part of a gang that would go and physically break up Nazi gatherings in Chicago. (If you don’t know there were American Nazis before the present resurgence of American Nazism, you would do well to read this and this and this.) Anybody who kicks a Nazi’s ass is oke with me. How could it spell Ruby’s doom? Fingeroth has the key. We’ll return to that.

First some fun facts I had to jot down. Ruby was from the Maxwell Street area of Chicago, which was used as a location in the 1979 movie The Blues Brothers. He was a boyhood friend of the boxer Barney Ross. One of his childhood nicknames was Sparky, after Barney Google’s horse Spark Plug (not a flattering nickname. Spark Plug was a nag who never came in). At one point Ruby was in a serious relationship with David Belasco’s granddaughter!

Ruby moved to Dallas in 1947 at around the same time that the mob was sending guys down there, and to Las Vegas too for that matter. His first club was the Silver Spur, a country joint where guys like Hank Williams, Hank Snow, and Tennessee Ernie Ford played. The Carousel Club was the strip joint he ran (and Danny’s book has many anecdotes concerning the girls who worked there). The most notorious was a lady named Jada (Janet Mole Adams Bonney Cuffari Smallwood Conforto Washington) who was known for pushing her act beyond the limits, and whose sudden departure from Dallas in November 1963 set certain tongues wagging. There was also the Vegas Lounge, which was strictly a bar, as well as The Sovereign Club, and many others. Ruby’s places were considered second rate, a little seedy, they were not the swankiest places in town. Other acts he presented included a tap dancing black kid named Little Daddy Nelson, and, believe it or not, The Band, back when they were still known as the Hawks.

Ruby was a hands-on manager. He was his own bouncer, and would toss trouble makers down the stairs, beat them with his fists, pistol whip them. There’s even an account in the book, unless I’m mistaken, that he ran the lights at one of his strip joints on at least one occasion. You do what you have to do to keep going. Like most guys who own nightclubs Ruby was always in deep financial trouble, in debt way over his head. And he had a jacket full of low-level beefs, from code violations to assaults, and thefts and the like. At the same time, he liked and cultivated the police, and would even go around and gladhand them, visit with them, bring them coffee. Pay it forward!

Ruby was a garrulous guy, he liked to court celebrities and other big shots. But he also seems to have been a kook, a nut, and a loose cannon. It is this aspect more than any other that makes the idea that he was anybody’s button man ridiculous. He had a big mouth, and a hair trigger temper. No one would ever trust him with a secret, let alone an assignment.

So, these are the factors that make a very strong case that Ruby acted alone:

1) Not only did he have no impulse control, he was a speed freak. Anything could set him off. He was always coming around, hanging around the action. Naturally he did just that when Oswald was in police custody, and naturally the police, who saw him every day, let him do so, and didn’t think a thing about it. He happened to be there, saw an opportunity, and took it.

2) He was attention-seeking, wanted to be accepted by everybody. The act of killing Oswald would make him a big shot. He wasn’t a long term thinker. He didn’t even think of arrest and prison as a consequence. He thought he’d get in the papers, and it would make his nightclubs more popular.

3) The most insightful thing to emerge from Fingeroth’s book, and something that has been ignored or downplayed by most commentators: his extreme sensitivity to Anti-Semitism, in a time and a place that was rife with Anti-Semitism. The John Birchers and other right wing fringe groups were all about linking Jews and Communists. The Kennedy administration had plenty of Jewish people in important roles in the cabinet, advisory positions, and so forth. This prejudice reached a fever pitch in Dallas just prior to Kennedy’s visit when someone (many think it was Oswald) took a pot shot at the psychotic army general and right wing provocateur Edwin Walker, making the atmosphere in the city very tense. Walker’s supporters blamed “the Jews” for the shooting. Ruby wanted to prove that “Jews have guts” and it seems to have been a major part of his motivation for killing Oswald. He wanted to be a Jewish hero. And…

4) He was in dire financial straights, and thus had nothing to lose. Maybe he even thought that as a hero, he’d be financially rewarded. You’ll have gleaned by now he wasn’t the sharpest knife in the drawer.

Ironically Ruby’s criminal associations prove to be one of the least convincing arguments as to his motivations for killing Oswald – somewhere in the vicinity of prejudice. Yes, crooks tend to be armed and lawless. But this was no well planned hit by the Organization in an attempt to cover up involvement in an assassination. I’ve always wondered, “How would that work, anyway?” The official verdict is that he “acted alone”. In the end, as Samuel Beckett would tell you, we all act alone. But I guess what people mean by a conspiracy is that someone hired Oswald, or coerced him into doing it or something. (Full disclosure, I was recently in a play by Jason Trachtenburg that proffered an even more radical theory – that Oswald didn’t even pull the trigger). But say Oswald did shoot Kennedy as most believe, and he was manipulated or assisted or something. I’m more inclined to look at the US military, US intelligence, and Cuban exiles than the Mafia. Organized crime is not THAT organized. And when you start looking at ALL those players, as the conspiracy theorists usually do, it gets especially preposterous, it starts to like look an Exquisite Corpse, you have to jump through a Rube Goldberg obstacle course of contortions to make your theory work, and when you have to do that you come full circle back to chaos anyway.

Was it chaos? Ruby seems to have had clearer motivation than Oswald did. Oswald has always been the real head scratcher. It’s not like John Wilkes Booth, who clearly hated Lincoln. Oswald by contrast was like a cipher who had a foot in all camps. But then Ruby upped the ante on the suspicions by killing Oswald so quickly, by having mob associations, and then dying so quickly himself. Ruby perished in early 1967 of cancer, pneumonia, and other factors. That too has struck many as suspicious, especially because he was on the eve of another trial (the sentence from his first trial was overturned on appeal, thanks to the intervention of William Kunstler). One of Ruby’s original lawyers was Melvin Belli, who went to to have many celebrity clients, and even appeared in episode of Star Trek. Jack Ruby was not the only guy in the story who compulsively sought attention! Somehow even Vincent Bugliosi found a way to get in on the action decades after it was over!

At any rate, Fingeroth’s portrait does a lot to forestall any idea of Jack Ruby as anything but an impulsive and paranoid character. Rabbi Hillel Silverman, who Fingeroth interviewed, spent a lot of time with Ruby during his last days, and his account leaves little room for doubt. By the way, Rabbi Silverman played himself in Stuart’s movie Ruby and Oswald. Michael Lerner played Ruby. (Danny Aiello played Ruby in Ruby, Brian Doyle-Murray played him in JFK).

Lastly I am delighted to learn that there is a neo‑Burlesque troupe in Dallas called The Ruby Revue. Tammi True, who had performed at the Carousel Club performed with the group until nearly the end of her life in 2019 at the age of 81. Way to milk it, honey!


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