39. The Blackhawks Win the Stanley Cup

Photo: Scott Strazzante/Chicago Tribune June 9, 2010 ESPN had named Chicago’s perennial hockey losers “the worst franchise in sports” in 2004. But when Rocky Wirtz became the team’s owner three years later after the death of his father, Bill, who was hated by fans as a penny pincher, he ushered in a new regime that … Read more

41. Jesús “Chuy” García Forces Rahm Emanuel into a Mayoral Runoff

Photo: Terrence Antonio James/Chicago Tribune February 24, 2015 Although he ultimately lost to Rahm, the Mexican American politician’s remarkable showing in the first round of voting put the incumbent back on his heels, despite García’s being outspent 12 to 1, and issued a wake-up call to the administration that the city’s growing Latino community didn’t … Read more

43. Lake Shore Drive Rerouting is Completed, Creating the Museum Campus

Photo: Jose More/Chicago Tribune June 4, 1998 It wasn’t the first time the city had fiddled with its most famous ribbon of asphalt — a realignment in the mid-1980s smoothed out the deadly S-curve — but it was certainly the most auspicious. By moving the northbound lanes to the west of Soldier Field and the Field Museum, which had … Read more

45. R.J. Grunts Opens

Photo: Candice C. Cusic/Chicago Tribune June 10, 1971 With 130 restaurants and 7,500 employees at its 2019 peak, Rich Melman’s Lettuce Entertain You Enterprises is the King Kong of Chicago restaurant groups. And it all started in Lincoln Park with burgers, a salad bar (some say the country’s first), and a name composed of the … Read more

46. Soul Train Premieres Nationally

Photo: Soul Train Holdings October 2, 1971 Until Entertainment Tonight surpassed it in 2016, Don Cornelius’s Chicago-born music-and-dance showcase — billed memorably as “sixty nonstop minutes across the tracks of your mind” — was the longest-running syndicated program in American TV history. By the time it went national a year after premiering on WCIU, it was already a huge … Read more

4. The Chicago Police Department Releases Video of Laquan McDonald’s Killing

Photo: Chicago Police Department November 24, 2015 Photo: Law Offices of Jeffrey J. Neslun Sixteen shots. In an instant, they transformed a CPD claim of self-defense against a Black 17-year-old into what eventually would be deemed second-degree murder. Police brutality had been documented in Chicago before, but this was different. The killing — and what many saw … Read more

49. Lollapalooza Makes Chicago its Permanent Home

Photo: E. Jason Wambsgans/Chicago Tribune July 23–24, 2005 It’s the most famous music festival in America, and after moving from city to city for years, Perry Farrell’s rollicking and increasingly slick brainchild came to Grant Park and stuck around, bringing in millions for the city annually ever since. It’s become the biggest cultural event of … Read more

6. Oprah Winfrey Opens Harpo Studios

Photo: Paul Natkin/Contributor January 15, 1990 Winfrey’s decision to ditch WLS-TV marked the moment she became more than just America’s most beloved TV personality. She was a mogul now. Film production (Beloved, Precious, Selma), made-for-TV movies (Tuesdays With Morrie, Their Eyes Were Watching God), radio, and of course The Oprah Winfrey Show — the West Loop studio’s … Read more

21. A Massive Blizzard Paralyzes the City

Photo: Chicago Tribune January 13–14, 1979 Forecasters predicted just a few inches of snow. Chicago was blanketed with 20. The city’s response was the real disaster: Plows didn’t arrive on clogged residential side streets until a week later. CTA trains bypassed ill-maintained stops in Black neighborhoods. Mayor Michael Bilandic’s tone-deaf responses to criticism — he compared himself … Read more

29. John Wayne Gacy is Arrested

Photo: William Yates/Chicago Tribune December 21, 1978 “If the devil’s alive, he lived in this house,” said one of the investigators. Twenty-six boys and young men, buried in a suburban crawlspace, with seven other bodies discovered nearby. As more details about the killer came out — the part-time job as a kid’s party clown, the handcuffs and … Read more