Windy City Gambit

 

In a small conference room deep within Chicago’s historic City Hall, two fresh college graduates, the ink barely dry on their diplomas, wait to speak with an aide to Mayor Brandon Johnson. One is a very attractive young woman, her short auburn hair styled in a sassy wedge, reminiscent of Dorothy Hamill. The other is a tall, well-built young man with a chiseled jaw and bright blue eyes. Both are dressed for success, as though they stepped out of the pages of a fashion magazine.

The door opens and Jamal Hemmings, aide to Mayor Johnson, steps into the room. Jamal is Black, mid-thirties, his shaved head glistening under the fluorescent lights. His Brooks Brothers suit is slightly wrinkled, the jacket unbuttoned, his tie loosened. He looks like an overworked political operative with too much on his plate, which is exactly what he is.

“Hello, I’m Jamal Hemmings.” He extends his hand to the young man who stands at the conference table.

“I’m Carlton Smith, but you can call me Chip.” He turns to the girl, also standing now. “This is my associate, Karen Jones. You can call her Karen.” He laughs, expecting a laugh in return, a little disappointed when his quip doesn’t land.

“Okay, Chip, Karen, what can I do for you?” Jamal glances at his watch.

Chip takes the lead. “I know your time is limited, so I’ll get right to the point—”

“Thank you.” Jamal has yet to crack a smile.

“As I’m sure you are aware, the Trump administration is planning to declare some sort of public safety emergency and deploy National Guard troops to Chicago.”

“Yes, we’ve heard that rumor. And we are prepared to fight back.”

“With all due respect,” Chip continues, “we think that is the wrong approach. We propose that you welcome the National Guard with open arms, roll out the red carpet, just as the President did for Putin up in Alaska.”

“You’re joking.” Jamal’s jaw has dropped several inches.

“We kid you not!” Karen chimes in. “You should welcome the troops to the Windy City as your honored guests. Give them a parade down Michigan Avenue. Make it a full-blown celebration of our beloved men and women in uniform. Call it ‘Summer with the Guard.’ Or fall, or winter, whatever the season.”

Jamal is gobsmacked. He looks at Karen, then Chip, unable to process what he’s hearing.

“Think of this,” Chip picks up the pitch. “Arrange tours for all service members to see the many beautiful and historic sites of Chicago. The Field Museum. Shedd Aquarium. Lincoln Park Zoo. The Art Institute. Grant Park. The Wrigley Building. I could go on and on—”

“And make sure the Guard is welcomed at all the fine eateries around town.” Karen’s enthusiasm has ticked up a notch. “I, for one, love Walker Brothers. I’m sure our troops would love to have breakfast at Walker Brothers. And how about a tour of all the great hot dog stands in the city? There’s nothing better than an authentic Chicago hot dog."

“Think of the boost to tourism.” Chip adds. “People will flock to the city to have their picture taken next to a Humvee or an MRAP. I’m sure the Guard will be happy to let kids climb in and out and all over those vehicles, even pose for pictures with their young fans.”

“And, what if we can convince them to give rides?” Karen smiles. “Leaving Navy Pier, cruising the Outer Drive and circling back. What kid wouldn’t love to ride in an MRAP? For a reasonable fare, of course.”

Jamal raises his eyebrows. He starts to say, That sounds pretty cool, but he bites his tongue. “Hold the phone,” he says. “What’s your part of this deal? What’s in it for you?”

“We are travel specialists,” Chip says. “We’ll promote the event, book travel arrangements, and provide concierge services. It goes without saying, we’ll find ways to monetize everything.”

Jamal is skeptical. “I don’t know. It’s an interesting idea, but I’m not sure the mayor will go for it.”

“We understand,” Karen says. “It’s a fresh approach, which is why we came to Chicago first. We want you to take the lead, get in on the ground floor, so to speak. Show America you are still the ‘City of Broad Shoulders,’ and ‘Hog butcher to the world.’”

“Okay, you can stop now. I’ve read Carl Sandburg.” Jamal smiles for the first time.

“We should tell you that we have meetings scheduled with several other cities.” Chip has lowered his voice to a conspiratorial level. “We’ll be meeting with officials in Milwaukee, Detroit, Oakland, and other major cities in blue states.”

“I mean, let’s face it,” Karen says. “We all know this is about the mid-term elections. The administration wants the National Guard in every major city that did not vote for Trump in 2024. You can be the first to have ordinary citizens—registered voters—having their pictures taken with Guard troops in front of ballot drop boxes. Think of the optics!”

“Take a look at this,” Chip says. He taps his iPhone a few times, and photos begin to scroll across the screen—National Guard troops posing with smiling civilians, Wrigley Field or Buckingham Fountain in the background, then a video clip of a chorus in camouflage uniforms singing, Chicago, Chicago, that toddlin’ town…

Jamal is shocked. “How the hell did you get those pictures and that video?”

Karen smiles. “It’s amazing what you can do with AI these days.”

Jamal is quiet for a moment, tapping his fingers on the conference table, considering everything he’s seen and heard. “Okay…send me the photos and the video. I’ll take the idea to Mayor Johnson. I can’t make any promises…but I think this idea has legs. That’s all I can say for now.”

They chat a while longer and then Jamal escorts Chip and Karen to the lobby, shakes their hands and bids them goodbye. As they hit the street in front of City Hall, Karen breaks into song.

“My kind of town / Chicago is / My kind of town…”

_____