The Little Black Book that Ruined Thanksgiving

The Little Black Book that Ruined Thanksgiving

If you were a bootlegger in Chicago during November of 1925, your Thanksgiving may have been filled with dread instead of gratitude.  Imagine waking up with plans to spend a lazy day feasting with your closest family and friends.  You retrieve the Chicago Daily Tribune from your doorstep and read the headlines.  Perhaps it jumps out at you or maybe it takes a second look, but within minutes you see the headline declaring that the feds have seized a safe that contains a “little black book” filled with inside tips, figures, names, and routines of Chicago’s elite bootleggers.

Are you in the book?  You won’t know until after the holiday.  The feds decided that opening the safe and disclosing the contents of the black book could wait until after Chicagoans celebrated gratitude.  The Chicago Daily Tribune’s article from November 26, 1925—Thanksgiving Day—eloquently reported that bootleggers in Chicago would “get little relish from their turkey and cranberries, while the brandy sauce and punch are sure to be delicacies of unpleasant suggestion.”  The federal agents expressed dismay that news of the confiscated safe and little black book had leaked to the press, but it’s possible to imagine that the federal agents were grateful their nemeses were sweating a little more on Thanksgiving.

Across Chicago, notorious bootleggers prepared to carve the turkey, probably refraining from enjoying a cocktail while doing so, wondering when the federal agents would arrive.  Did they tell their spouses or children before or after the blessing?  The article relayed the news that the book, secured by armed guards, contained names, bills of sale, amounts, and routes determined safe from federal Prohibition agents.  Because if you’re going to commit a federal crime, you should absolutely sign a bill of sale.

We’ve all sat through difficult family holiday meals, but perhaps nothing as tense as Thanksgiving 1925.

The book indicated that as much as $1,000,000 each month had passed through the raided building.  Adjusted for inflation, that would be more than 14 million dollars per month in 2019.  The book also contained personal details about the bootleggers, and the Prohibition agents chasing the booze.

But because this is Chicago in the 1920’s, the story couldn’t possibly be as straightforward as it first seemed.  When the feds arrived at the building to be raided—just across from the Criminal Courts Building, ironically—they found one of their own men there, just hanging around.  The name of the federal agent wasn’t released but the feds did note that “his presence establishes connections considered of great importance.”  Do you think?

What role did the internal revenue collector have in the story?  Was this Chicago’s only black book of notorious Prohibition dealings?  Sorry, no spoilers on what becomes of the internal revenue collector or Chicago’s history of finding black books.  You have to take the tour to hear the rest of that story!

Enjoy your Thanksgiving, Chicago! May it be far less stressful than Thanksgiving 1925.

Written by Amy Williams

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