Hopefully, the new boss of Choose Chicago is up to the job
After a grueling, year-long nationwide search that surely required sifting through no fewer than three LinkedIn profiles and maybe a LinkedIn Learning certificate or two, Chicago has finally chosen a brave soul to take on what may be the worst job in America: CEO of Choose Chicago, the city’s beleaguered tourism agency.
The lucky winner? Kristen Reynolds of — wait for it — Long Island.
Yes, Long Island. That charming suburban sprawl where the biggest threats are Hampton’s parking enforcement and being overcharged for rosé. A place known not for its thrilling urban grit or vibrant gun violence statistics, but for seasonal beach traffic and wine tours. It’s like recruiting a surfing instructor from Des Moines to run a seiche evacuation plan.
Yet here Reynolds is, parachuting into a city where the “hospitality industry” now means boarding up your Magnificent Mile retail location with plywood and praying no one sets it on fire during the next public protest. Welcome, Kristen! You’ve got this!
The vacancy that spoke volumes
The job had been vacant for over a year — a full year. Let that sink in. In one of the largest cities in America, with a six-figure salary and a $35 million budget to promote itself, not a single local was deemed fit, or perhaps foolish enough, to take the helm. After the last CEO stepped down in a hurry (and after less than two years on the job), it seems everyone else politely declined to be the next captain of this listing ship.
So Chicago reached out to the East Coast — because when you’re struggling to sell a city plagued by smash-and-grabs, open-air fentanyl fiestas, and that charming aroma wafting out of the Red Line, you call someone who once promoted the Jones Beach air show.
From rosé to realpolitik
Reynolds, to her credit, brings a stellar resume. On Long Island, she “put the region on the map,” according to a press release that seems unaware the map already included Long Island. She doubled the tourism budget, hyped the Hamptons on TikTok, and even hosted a podcast called Long Island Tea — which we can only assume was an extended Yelp review for brunch spots in Nassau County.
Now she’s tasked with selling Chicago, where she may need a few Long Island Ice Teas herself after a hard day trying to get conventions and tourists to choose our toddling town where the streets run red with blood, violence maps are color-coded like a perverse game of Risk, and a retail corridor where luxury brands once thrived now resembles the aftermath of a Call of Duty mission.
The Magnificent Mile is no longer magnificent. It’s mostly “Vacant Retail Space: Call for Lease.” Friends, it’s not a shopping district — it’s a scavenger hunt for the last surviving Banana Republic. Nobody calls it “Boul Mich” these days.
Ethnic realities and political optics
It’s also worth noting — purely as an observational footnote, of course — that Ms. Reynolds is perhaps not the most demographically representative choice for a Brandon Johnson administration that talks a big game about equity and inclusion. Reynolds is not from Chicago. She’s not from the West Side, the South Side, or anywhere remotely resembling the city’s core demographics. She’s a Texas-born, Arizona State-educated suburban marketing executive who has likely never tried a mild sauce combo or waited forty minutes for a CTA bus that never came. She clearly doesn’t fit the profile of the senior executive under the Johnson administration.
But, hey, her husband is from Chicago. And her daughter goes to Loyola. So, by that logic, she’s practically 79th and DuSable LSD adjacent.
Let’s talk about the job itself
Think about the brief here: Promote Chicago as a “top-tier travel destination” to a global audience that increasingly knows it as the place where your luggage might get looted before you reach baggage claim. You’re not selling a tropical beach or a desert oasis — you’re selling a city where one of the biggest tourist attractions is still Navy Pier, a place only slightly less thrilling than a Midwestern airport food court.
You’re tasked with telling the world that Chicago is safe, vibrant, and worthy of their business dollars — while major conventions look longingly at Orlando and Las Vegas, and international tourists begin factoring body armor rental into their hotel budgets.
Your budget? $35 million: Just enough to produce a slick ad campaign and maybe, if you’re lucky, convince a few flyers who miss their connections to take the Blue Line downtown to kill a few hours.
Nothing says “welcome international guests” like being branded as the murder capital of America by the leading cable news network.
Godspeed, Kristen
Reynolds says she’s ready to “shout how wonderful Chicago is from the global stage.” That’s sweet. But around here, shouting usually just draws muggers. You might want to keep it to a whisper or borrow a few foot soldiers from the mayor’s legion of Praetorian guards.
To take this job in this city, at this moment in history, is either courageous or clinically diagnosable. Possibly both. But if anyone can convince the world that Chicago is worth visiting—despite the boarded-up stores, crumbling infrastructure, and shootouts on Lakeshore Drive—it’s someone who once sold Long Island as exotic.
Kristen, welcome to the job. It’s the worst in America. But it’s yours now.
Allow me to extend a Contrarian helping hand: As a lifelong Chicagoan, I am more than willing to (for a small fee much less than her rather large salary) provide some suggestions on creative idea ideas to use some of Chicago’s weaknesses and turn them into strengths in the form of innovative tourist attractions for example,
- For a long time, one of our big tourist attractions has been Chicago gangland tours, which basically put you in a bus or on a bike to see some of the old Al Capone roaring 20s-era gangland sites such as where John Dillinger got killed and all that, but I’ve always thought given that we have a very robust, vibrant gang crime culture here that we ought to offer tours of contemporary gang bangers rather than dead white males where you can see the actual shootings taking place, live as they happen. Instead of orange safety vests and bikes, we can hand out bulletproof vests and SWAT team body armor, and you can do some ride-alongs with the tactical units of our fine Chicago Police Department. Unfortunately, Shotspotter is gone, but you can still go right to the scene of 911 calls and maybe catch active shootings in progress, or at least watch the police do the after-action clean up and count the shell casings, chalk outline the dearly departed, put the yellow tape around the crime scene and all that good stuff — you know, real-life action, CSI style! Much more exciting and relevant than 100-year-old historic dead, white male gangsters.
- Another fun activity would be to monitor social media and offer excursions to some of our more robust, exuberant youth events where the flash mobs assemble at places like North Avenue Beach and Streeterville. These are very exciting opportunities to experience diversity and inclusion, Chicago style! As Brandon Johnson has said, these kids are just expressing themselves! It’s a great urban anthropology opportunity where you can not only enjoy yourself in our magnificent summer weather but can experience the vibe of the city.
Catch the excitement when gunshots ring out and stampede the crowd! Watch as police sweep and clear the area with their 4-wheelers! Fun stuff!
- Another enjoyable idea is to take a tour of our legacy industrial sites. Tour some of the toxic waste superfund sites on the southeast side. See the environmental racism that afflicts our community firsthand. Great stuff! Hazmat suit rental not included.
- Neighborhood tours. Here’s your chance to get out into the neighborhoods. See Woodlawn and South Shore. The real fun begins when the sun goes down! Don’t forget to duck! I mean these are thrills and excitement that you just can’t get at places like Great America, and they bring tourism into the community. I’m sure Mayor Johnson would be very amenable to this sort of thing — his neighborhood would be a great tour location. You know you haven’t really seen Chicago, which we used to refer to somewhat pejoratively as a Gilded garbage can where the Gold Coast, where most tourists spend their time, just doesn’t give you a real feel for the grit, humanity, and pathos of the city’s complicated matrix of neighborhoods. Here’s your chance to see it all — the bad, the worse, and the ugly!
- Real-life Chicago Police and Chicago Fire — Wondering if the TV shows with model-quality drop-dead hunks and gorgeous female cops and firefighters are authentic? Spend a day with real cops and firefighters, looking worse for wear of 20 years on the job. Watch cops get their windshields twerked and shot at with switches suitable for military use by fun-loving youth. Watch firefighters get shot at by merry pranksters who summon them with false alarms. Spend time at the Northwestern and Christ Hospital trauma center ERs on Saturday nights that make MASH look tame by comparison! Big fun in the nitty gritty city. Great stories to tell the folks back home!
- How about a walking tour of Lower Wacker Drive? Start on Grand Avenue and head south— along the way you’ll encounter some of the most colorful Chicago characters! The denizens of the deep levels of Lower Wacker will give you a warm welcome as you go where very few tourists ever go and live to tell the tale. Particularly educational for international visitors from orderly societies like Japan! Take all the photos your heart desires! See LOWER Lower Wacker, aka, the third level of Hell. Stop by and visit the friendly staff at the Auto Pound (a must-see for out-of-towners along with the Wiener Circle, to experience customer service CHICAGO style).
Ahh, Wacker Drive — so many levels, like multidimensional chess, and you’re the pawn!
- Another great idea is a thunder run down the always exciting I-90 corridor around midnight on Saturday night. Speed down the Eisenhower and the Dan Ryan, in heavy traffic careening down the multi-lane expressways from the West side to the south side while attempting to set a world land speed record! Feels like you’re Mel Gibson in the Road Warrior movies- positively post-apocalyptic! Plenty of lane changes-not many turn signals! Gotta take them by surprise to cut in line! See 8-lane lane changes! Drive by gang initiation shootings! Fiery crashes! Never a dull moment! Makes the Chicago NASCAR race pale by comparison! Big fun indeed! Can’t get that on Long Island!
- Cinco de Mayo Festiva — Hop in your low rider and be a part of the world’s largest traffic jam with zero traffic control! Things can get to be things, so keep your head low in your low rider! After taking 4 hours or so to move two blocks in gridlocked downtown, head back to your hotel and listen to the horns blare and music blast ALL NIGHT LONG! Great fun, LatinX style!
These are just a few ideas — plenty more novel urban adventures are available in the city of big shoulder holsters
Good luck. You’ll need it.
