24. The City Council Ratifies the Parking Meter Deal

Photo: Phil Velasquez/Chicago Tribune December 4, 2008 Rushed through the City Council with virtually no debate or public scrutiny, Mayor Richard M. Daley’s deal leased Chicago’s 36,000 parking meters to private investors for 75 years. The city got a one-time sugar rush of $1.2 billion, but the investors made back that money in 10 years, … Read more

23. Jane Byrne is Elected Mayor

Photo: John Irvine/Chicago Tribune April 3, 1979 “Nobody saw me coming. I was like a joke,” Byrne remembered years later in a Tribune interview. The former consumer sales commissioner beat the machine-backed Michael Bilandic by attracting a curious coalition of disgruntled Republicans and progressives, including Rev. Jesse Jackson, then won the general election with 82 … Read more

20. The Last Cabrini-Green Tower is Demolished

Photo: Brian Cassella/Chicago Tribune March 30, 2011 Cut off from the amenities of surrounding neighborhoods, its public spaces defaced and plagued by gang activity, the Cabrini high-rise complex had become the reigning symbol of a failed experiment in urban planning and a yearslong push by Richard J. Daley to contain and confine Black communities. When … Read more

22. Operation Greylord is Revealed

Judge Richard LeFevour was sentenced to twelve years in prison for his role in the Greylord scandal, which revealed corruption within Cook County’s court system. He was convicted of taking thousands of dollars in bribes to fix traffic cases. Photo: Frank Hanes/Chicago Tribune August 5, 1983 The FBI probe into corruption in the Cook County … Read more

32. The White Sox Win the World Series

Photo: Scott Strazzante/Chicago Tribune October 26, 2005 Some saw the team’s 88-year world-championship hiatus as divine punishment for 1919, when Sox players threw the World Series. When the South Siders finally claimed the crown with a four-game sweep of the Astros, long-suffering fans ecstatically sang “Na Na Hey Hey.” “The Sox have been the stepchild … Read more

33. The Digging of the Deep Tunnel Begins

Photo: Zbigniew Bzdak/Chicago Tribune August 25, 1976 Conceived half a century ago and not scheduled for completion until 2029, it’s one of the biggest civil engineering projects ever undertaken. Engineers called this superhighway of sewers and reservoirs a “storm bottle,” designed to solve one of the most intractable problems of our low-lying waterfront city: street … Read more

36. Gene Siskel and Roger Ebert Make Their TV Debut

Photo: Library of Congress September 4, 1975 Filmed inside a WTTW studio, the local monthly show Opening Soon at a Theater Near You — which later morphed into Sneak Previews and then At the Movies — would make two Chicago newspapermen into the nation’s most recognizable film critics. Their weird chemistry, at turns chummy and openly acrimonious, was “not … Read more

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