Credit: YouTube
Tech billionaire Peter Thiel recently told a Chicago audience: "If you are a very talented person, you have a choice: You either go to New York or you go to Silicon Valley."
Tech billionaire Peter Thiel recently told a Chicago audience: “If you are a very talented person, you have a choice: You either go to New York or you go to Silicon Valley.”Credit: Reuters

There’s been an unfortunate recent outbreak of Second City syndrome—the nagging inferiority complex that causes Chicagoans to reflexively overreact to every dig and perceived slight directed at the city, even if it’s much ado about nothing. 

Take, for instance, Peter Thiel’s recent remarks: “If you are a very talented person, you have a choice: You either go to New York or you go to Silicon Valley,” the tech billionaire told a group at Roosevelt University last week. The implication: Chicago is flyover territory for anyone who’s anyone. Thiel later claimed that he was speaking in “metaphor” and didn’t mean to insult Chicago.

But the damage was done. The Tribune relayed the original comment with prose so sarcastic, you can almost feel reporter Kim Janssen’s eyes roll out of his head: Thiel “deigned to make a flying visit to our cow town to share a few pearls of wisdom.” Plenty of other Chicagoans took the Trib‘s cue and began venting their spleens in anger on social media.

But let’s consider the source. A few years ago, the PayPal founder was just another oligarch aspiring to be a hero from an Ayn Rand novel, funding under-the-radar projects to cure aging and building city-states on platforms in international waters—a kind of floating Galt’s Gulch. Over the last year, Thiel’s gone public, and it hasn’t been pretty: he spoke at the Republican National Convention in support of Donald Trump, and also followed Trump’s example by turning a petty grievance into a lawsuit aimed at silencing the press (and ended up bankrupting Gawker Media in the process).

Coming from the mouth of Silicon Valley’s supervillain, that’s a comment Chicago should’ve just smirked at and let go. 

And it’s important to keep in mind that when Thiel says “very talented person,” he’s using double-talk to describe “entrepreneurs,” which itself is also code for rich, young, white-collar professionals who specialize in global capital and tech start-ups—the new techno-meritocracy. Maybe Pete isn’t aware we’ve got plenty of those assholes “disrupting” these parts ’round here.

A sign from the Brianna and Jaelin Walking Tour in Edgewater earlier this month.

Chicago’s grapes were similarly sour toward so-called “YouTube couple” Jaelin and Brianna Joy White. The newlyweds, who look like freshly scrubbed stars of a Disney Channel sitcom, moved from Arizona to Edgewater earlier this summer to start their new lives full of house-flipping, vlogging, and conspicuous consumption. But after a couple of colorful encounters with locals, they fled Chicago at a rate faster than a Jake Arrieta fastball.

It’s difficult to say exactly what happened, because the couple’s hysterical account, documented in a 16-minute YouTube video called “THE REASON WE’RE HOMELESS RIGHT NOW … (no clickbait) STORYTIME,” is nigh incomprehensible. Chock-full of meandering twists and turns, it culminates with Jaelin claiming he was punched by a “sketchy” guy outside a Subway on the north side. They were so shaken by the incident that they hightailed it back to the desert after just a single day in town.

It’s easy to see why the video went viral: it showcased the self-parodic excesses of privileged teens who have more YouTube subscribers than common sense. Meanwhile Chicagoans were offended that the couple, no matter how vapid, made the city seem like some kind of postapocalyptic hellscape. 

But the level of venom in tweets and YouTube comments directed at the couple was disproportionate, so much so that a New York magazine headline reads: “The Dramatic Saga of a YouTube Couple’s Escape From Chicago Has Turned the Entire City Against Them.” The Whites reportedly received a deluge of hateful criticism, from those calling them “privileged white trash” to those wishing that the couple be shot.

Then came the Brianna and Jaelin Walking Tour, a mocking re-creation of their ill-fated jaunt through Edgewater, organized earlier this month by a local improv performer. Only about 150 of the 3,500 who RSVP’d on Facebook attended, but that’s still a lot of Chicagoans strolling around a neighborhood’s fast-food joints in a show of superiority to a couple of clueless kids from Arizona.

It’s understandable why so many of us feel the need to take up the mantle of white knight and come to Chicago’s defense. We’re lacking in the PR department—especially as of late. It seems nearly every bit of news, every Google search result, every salvo from the national media is relentlessly negative. Justifiably so in many cases: Mayor 1 Percent, police cover-ups, population loss. Just yesterday came a report that Chicago is responsible for almost half the increase in U.S. homicides.

In light of all those real problems and the resultant perceptions that give us a bad name, we’ve got to be better about knowing when it’s best to go on the defensive and when the City of Big Shoulders should let something roll off its back.