Saturday, February 14, 2009

A Very Uptown Valentine

Today we remember "Machine Gun" Jack McGurn, a member of Al Capone's gang, forever associated with St. Valentine's Day. Why? Because our fellow Uptowner was responsible for the famous 1929 St. Valentine's Day Massacre, planning it with boss Al C.

Closer to home, McGurn was owner of the Green Mill Cocktail Lounge, which was in the heart of the territory controlled by Capone rival Bugs Moran. Because of McGurn's ownership stake in the club, the Green Mill served booze supplied by Capone, who was also a frequent patron.

The Green Mill was home to singer Joe E. Lewis in the mid-1920s. When Lewis refused to renew his contract (because another gang offered him more money to appear at a club located at Clark & Diversey), McGurn decided to persuade Lewis to stay on. His version of persuasion was to have Lewis's throat slit, cutting part of his tongue off, and leaving him for dead. Lewis survived, and actually opened 11 weeks later at the Rendezvous Café (where the Days Inn Lincoln Park is located now).

But what makes Valentine's Day particularly a day to remember Jack McGurn was his death. By 1936, he was out of favor with the Mob and destitute. On February 14, he was bowling alone when two men with machine guns assassinated him. They left his body in the bowling alley with a Valentine pinned to it, reading:

"You've lost your job,
You've lost your dough,
Your jewels and handsome houses,
But things could be worse, you know,
You haven't lost your trousers."


  1. Why can't our modern day gangsters be as poetic?

    Now and days, it's all tag, tag, tag, hand sign, hand sign, zoning permit, tag, TIF, tag - with no concern over prose.

    A sad sign of the times, indeed.

  2. The gangster dress has changed a lot over the years too. Back then it was three piece suits with fedoras, gold chain pocket watches and cufflinks.

    But today it's t-shirts, hoodies, basketball shorts, print dresses and blouses with an obscene amount of cleavage, baseball hats cocked to the side, jeans dragging below the underwear, birkenstocks below shapeless dresses and bandanas.

    What ever happened to class?

    Today's youngsters in poverty don't have the well dressed role model to look up to anymore. The best they can strive for is "the oxford shirt when looking for a TIF handout" look.

    Sad sign of the times, indeed yo. Sad times indeed.

  3. I wonder if the gangsters of old were living in tax payer funded housing?

    Chicago needs a modern day Elliot Ness. I suppose Patrick Fitzgerald will have to do for now.

    I sent Pirate a Sarah Palin Vanlentine, and he sent me back that "Sexy" picture of Barack coming out of the ocean. What gives?

  4. Eliot Ness, who never met Al Capone, was not as involved in the tax evasion case that Robert Stack and Brian DiPalma would have you believe.

    After leaving Chicago, Ness took his show to Cleveland, where he ended up as a rather unsuccessful mayor, and eventually found himself a divorced alcoholic.

    I would hope Fitz doesn't take that route.

    Though, in Ness' defense, back then he had Fed support to go after the gangsters.

    Now, the gangsters have become the Feds.

    And, gangsters of old held to an unwritten code of behavior to stave off the heat.

    They paid their rent. They donated to charities/operated soup kitchens(Capone); owned and operated flower shops (Dion O'Banion) Other than the rum-runnin', gamblin', hookin', extortin' and murderin', they were generally well behaved people - at least in the eyes of the general public.

    They certainly didn't target civilians, and most certainly did not suckle the public teet.

    For the most part, gangsters were tolerated as long as they (mainly) kept the violence amongst themselves.

    After all, they were serving a public not interested in prohibition.

    There was no money in killing your client base.

    That all changed after the St. Valentine's Day Massacre and most importantly, yet not as publicly known, was the murder of a Tribune reporter, Jake Lingle, in the Randolph train tunnel, downtown.

    Back then, the newspapermen were, for lack of a better term, untouchable.

    Anyway - not that I'm saying gangsters of old were better "people" than their ignorant, mouth-breathing monstrous product of horrible welfare/entitlement system, lazy-ass unmotivated brethren.

    I'm just saying they were a little better behaved and certainly better shots.

    They also would handle the extortion of local shop-keepers ... (complete that sentence for yourselves).

    But there is one similarity - back then, abhorrent, greedy, self-serving, unworthy politicians protected their favorite gangsters and showed them preferential treatment when it served them, too.

  5. I don't like this thread. What do most people know about the gangster life of old or the one today if they didn't live it or aren't living it?

    But carry on. I support your right to opine because I am Uptown Update too.

  6. Thanks for the knowledge Yo.

    Awe come on Sass, us boys like to talk about the blood and guts now and then. Makes us feel masculine on this the most feminine of holidays.

  7. What do most people know about the gangster life of old or the one today if they didn't live it or aren't living it?

    I didn't live in Egypt and have read much about the Pharaohs.

    Books, newspapers, magazines, etc are wonderful things.

    As is the experience of talking to people who actually lived back then.