Thrilling City: Ian Fleming in Chicago

Chicago is the kind of city that James Bond would have loved. He might well have needed to go there more often on assignments but there always seemed to be enough trouble off the coast of Miami to pull him away. Ian Fleming however made it there and used it for inspiration for some his characters and plots as well as a key stop in his tour of the world’s Thrilling Cities.

Ian started off on the right foot, flying over while consuming Old Forrester on the rocks and reading Nabokov‘s ‘Invitation to a Beheading’ just to get in the mood, also remarking that:

“I never saw a single other passenger reading a book. Everyone read magazines or studied business correspndence, or just sat ad looked out of the window t nothing.”

Well, he’d be equally disappointed by today’s digitally minded travellers.

When Ian landed in Chicago, he was determined to see the crime hotspots but had mixed success. He noted the dangerous and congested airport but was enchanted by the 25 miles of lakefront by the Great Lake Michigan.

His visit there was fancifully written up by the writer William F. Nolan, whose article ‘Ian Fleming in Chicago – A Sinfull Day with the 007 Man‘ provides some intriguing insights. In the article, Nolan remembers a day spent in Ian’s company along with his friend Charles Beaumont. They also met up at the offices of Playboy, also in the company of Ray Brennan of the Chicago Sun Times. Fleming, dressed in his idiosyncratic blue raincoat and polka-dot bow tie.

Alledgedly, Beaumont called Nolan and said:

“Fleming’s in town. He’s going to tour all the gangland spots. Get here!”

All three then set out in a Cadillac to tour the Capone-era sites.

None of it can be verified very well and as can be the case, chance meetings with the great Ian Fleming were often spun with hyperbole. It is a little suspicious fact that Nolan reports 40 year old conversations verbatim – perhaps there are one or two bits of actual remembered dialogue. Nevertheless, if there were kernels of truth, the Ian decidedly liked Chicago and might have considered using it as a location for one of his novels.

Over the years, Chicago has had a dubious reputation for crime – sometimes fair, other times unfair. During the 1920s, The Purple Gang of Detroit were involved in the St. Valentine’s Day Massacre – essentially the result of a turf war with Al Capone’s gang. The Purple Gang were referenced four times in the James Bond novels. They supply two goons to the Spangled Mob in Diamonds Are Forever; in The Man with the Golden Gun, Francisco Scaramanga is said to have killed one of their hitmen; and in Thunderball, Blofeld tells of an operation where SPECTRE kidnapped a Purple Gang member’s daughter.

They are also one of the gangs employed by Auric Goldfinger in his raid on Fort Knox, which gave us one of the most famous lines in all the books:

Mr Bond, they have a saying in Chicago: ‘Once is happenstance. Twice is coincidence. The third time it’s enemy action’. Miami, Sandwich and now Geneva. I propose to wring the truth out of you.

One can’t help but picture Ian jotting down notes in this notebooks they raced along to each stop along the way; from Dion O’Bannion’s flower shop to The Biograph Theater, where gangster John Dillinger was shot. Chicago was certainly a fertile place for villainous inspiration. Fleming remarked that it was “dingy” but delighted in finding the original bullet holes, perhaps stirring up some ideas for his creation.

The Biograph Today

After hopping around the crime spots, Fleming remarked in Thrilling Cities that “that afternoon, to wash the smut of ancient crime out of my mind, I repaired to the Chicago Art Institute” for which he gave a rave review of it, calling it “my favourite picture gallery in the world,” with the “finest French Impressionists outside Russia”.

But if we are to believe William Nolan, Fleming also remarked that “Those pictures have no goddamned right to be in Chicago”–this perhaps summed up Fleming’s paradoxical attitude, not only to Chicago but America in general.

Fleming parted ways with his companions with Bond-esque aloofness on the steps of the Institute:

“I’m frightfully sorry gentlemen, but I’m afraid we must part company. I can’t very well continue to interview Chicago while you are interviewing me.”

The Art Institute of Chicago Today

Chicago made an impression on Fleming and it would have been deliciously fun to have put Bond there to see how he would fare. Even Fleming thought so…

“Bloody shame to waste all this on a travel book. Have to send Bond along to the Biograph. Maybe get him involved with the Mafia. There’s still plenty of crime in Chicago.”