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The ’90s, Not the ’20s, Were Chicago’s Golden Age

It wasn’t just the Bulls that usurped the city’s gangster image, but Wilco, Liz Phair, Charlie Trotter, and a state senator named Barack Obama.

Michael Jordan and Scottie Pippen during Game Two of the 1998 NBA Finals against the Utah Jazz   Photo: Phil Velasquez/Chicago Tribune

The Last Dance, the ESPN docuseries about the 1997-98 Chicago Bulls season, captures a golden moment in the history of Chicago sports. But that Bulls team was just one aspect of what was a golden decade in the history of Chicago — maybe the greatest decade the city ever had, outshining even the Roaring Twenties.

In the 1990s, Chicago transformed itself from a would-be Rust Belt casualty to the global metropolis it is today. If you weren’t living in Chicago in the ’90s, you didn’t just miss out on some great basketball — you missed out on life.

The decade didn’t start out so promisingly. In 1992, U.S. Steel South Works, which had once employed 20,000 workers in Chicago, produced its last bar of product. But that, as it turned out, was emblematic of Chicago’s economic past giving way to its future. 

As I wrote in 2013, in Nothin’ but Blue Skies, professional services became Chicago’s new product. In 1986, the city’s ad agencies, investment banks, law firms, benefits consultantts, accountants, and management consultants employed 17,000 people; by 1998, they employed 60,000. Chicago was better equipped than any other Midwestern city for the day when trading something became more profitable than making something. It had a more diversified economy than its Midwestern rivals: Besides forging steel and slaughtering cattle, Chicago published books, wrote insurance, traded grain futures, and issued bank loans. As the headquarters of the Mercantile Exchange and the Board of Trade, it was the Midwest’s financial hub. Due to its central geographic position, O’Hare was the world’s busiest airport, making it a plum spot for consulting businesses that flew employees all over the country.

As Chicago became a destination for those new employees — and a whole lot of Big Ten graduates — it gained population in the 1990s, the only time since the 1950s a Midwestern metropolis has done so. (I moved to Chicago in 1995, from Decatur, a town still reeling from deindustrialization.)

In 1996, the Democratic National Convention was held in Chicago — its first time back since Mayor Richard J. Daley’s cops beat up anti-war protestors in 1968. A few police officers wore t-shirts reading “We Kicked Your Father’s Ass in ’68…Wait ’til You See What We Do To You.” 

But Daley’s son, Mayor Richard M. Daley, wanted to show the delegates how much Chicago had changed since his father’s day. More from Blue Skies:

[Daley’s] patronage workers scrubbed graffiti off walls, tore down empty buildings, and towed abandoned cars. He planted pots of flowers on sidewalks and pedestrian overpasses, and surrounded parks with black wrought-iron fences. Nelson Algren would not have recognized the city he compared to a woman with a broken nose, but Chicago had to stop looking like an industrial city before it could become an international city. The Loop was changing, too, from a combat zone of taverns and adult bookstores to a place where executives paid $5 million for a condominium.

As Gery Chico, Daley’s chief of staff in the 1990s, told me in 2011: “When I was a kid working here in the late ’70s, this town closed up at five. There was nothing down here. Maybe a few movie theaters. But the streets were cleared and the place was empty. Today, I live downtown, along with 56,000 other people and a lot of executives who find it very convenient to be in the central area.”

Charlie Trotter poses with his Outstanding Chef medal at the 1998 Beard Awards. Photo: Chicago Tribune

In the 1990s, Chicago was home to two of the most famous people in the world — Jordan and talk show host Oprah Winfrey — and a person who would become more famous than both of them: Barack Obama, who won his first election, to the Illinois State Senate, in 1996, beginning a career that would help erase the city’s image for provincialism and corruption.

Meanwhile, we were winning recognition as a world-class food city: during the 1990s, Charlie Trotter wrote two best-selling cookbooks, hosted a PBS cooking show, and was named the nation’s Outstanding Chef by the James Beard Foundation. Rick Bayless received that same award in 1995, for his work at Topolobampo and Frontera Grill.

Of course, the Bulls played a big role in the city’s 1990s renaissance. The United Center was built to hold the crowds who wanted to see Michael Jordan play. Slowly, Jordan himself replaced Al Capone as the international face of the city, successfully usurping the gangster image Chicago had been trying to shake for decades. In 1997, I met a French exchange student in Chicago, whose father had told him the city was famous for bootlegging during Prohibition. But the student just wanted to meet Michael Jordan.

Musically, Chicago’s ’90s rock scene was second only to Seattle’s. Liz Phair’s Exile in Guyville was No. 20 on Rolling Stone’s 100 Best Albums of the ’90s. We had an answer for Seattle in Smashing Pumpkins, and it was here that Courtney Love purportedly broke it off with frontman Billy Corgan and met Kurt Cobain, after a Nirvana show at Metro.

Jay Bennett and Jeff Tweedy of Wilco perform at Lounge Ax on January 9, 2000, the week before it closed. Photo: Kevin Tanaka/Chicago Tribune

The 2000 movie High Fidelity captured the Wicker Park scene of that decade, mostly from a record store at Milwaukee and Honore. One of its final scenes, though, was filmed at Lounge Ax, the Lincoln Park nightclub owned by Sue Miller, who married Wilco founder Jeff Tweedy in 1995. When the ’90s ended, so did Lounge Ax. But its website is still alive, with a list of the acts who performed there during its own last dance in January 2000. Among them: Wilco, Tortoise, Robbie Fulks, Andrew Bird, Eleventh Dream Day, and Shellac.

The next year, MTV’s Real World moved its cast into a building on North Avenue that had once been occupied by the coffee shop Urbus Orbis, which the Reader wrote had fallen “prey to the gentrification it helped attract.”

That sums up the ’90s in Chicago pretty well: It was an exciting time here because the city was in the process of becoming something new. It was the midpoint of its transformation from the Chicago of The Blues Brothers to the Chicago of The Time Traveler’s Wife, a book written, set, and later adapted for screen here. Once Chicago became that new city, it wasn’t quite as exciting anymore. As I’m sure even the Bulls would agree, the journey was more fun than the destination.

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