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Q.1
February 2017: A friend says Ret. Vice Adm. Bob Harward considered Trump’s request he become National Security Adviser a ______. *

Q.2
March 2017: U.S. Atty. Gen. Jeff Sessions has recused himself from an investigation into _____. *

Q.3
April 2017: Chicago’s veteran horror-movie host, Svengoolie … later this month begins a guest shot in _____. *

Q.4
May 2017: _____’s embattled CEO, Oscar Munoz, has been groveling before a U.S. House committee today. *

Q.5
May 2017: “The only thing your mouth is good for is being _____’s c_ck holster,” Colbert said. *

Q.6
July 2017: Sen. John McCain says his party’s health care overhaul is “probably going to _____.” *

Q.7
August 2017: A nationwide manhunt is on for an _____ staffer and a Northwestern University professor in connection with the murder of a man in a Chicago luxury apartment. *

Q.8
September 2017: Mayor Emanuel and Gov. Rauner have assembled a 600-member committee—including some of Chicago’s most high-profile executives in the fields of business, technology and the arts—for an “all hands on deck” effort to lure _____’s new headquarters to the city. *

Q.9
October 2017: The iconic _____ sign is coming down from the facade of 350 N. Orleans St. *

Q.10
October 2017: The Illinois House has voted, over Gov. Rauner’s veto, to require schools teach elementary students _____. *

Q.11
October 2017: Chicago guy George Papadopoulos, a 2009 _____ graduate, is first to plead guilty in special counsel Robert Mueller’s investigation of Russian efforts to meddle in the 2016 election. *

Q.12
November 2017: The Chicago Headline Club … mourns the abrupt shutdown yesterday of _____. *

Q.13
December 2017: U.S. Rep. Trent Franks of Arizona announced his resignation after revelation he was under investigation for asking two female employees to consider becoming _____. *

Q.14
March 2018: WLUP-FM 97.9 has been sold to a company that plans to convert it to a _____. *

Q.15
March 2018: The decision to close the remaining _____ stores puts 31,000 workers out of work—with no severance. *

Q.16
May 2018: AT&T CEO Randall Stephenson says the company’s $600,000 hiring of President Trump’s hapless _____ as a consultant … has left the company’s reputation “damaged.” *

Q.17
June 2018: ABC is bringing back Roseanne Barr’s TV show without _____. *

Q.18
June 2018: Hours after the murders of four of its journalists and a sales assistant, the _____ nevertheless went to press for today’s edition. *

Q.19
July 2018: A Cook County Forest Preserve District police officer caught on Facebook video failing to intervene as a drunken man harassed a woman who was wearing a _____ T-shirt has quit rather than face disciplinary measures. *

Q.20
July 2018: _____ has announced his purchase of the Chicagoist website. *

Q.21
October 2018: The chief watchdog for Cook County government accuses Democratic gubernatorial candidate J.B. Pritzker of “a scheme to defraud” the county by _____ and otherwise letting a home he’d bought fall into disrepair. *

Q.22
January 2019: Mayoral candidate Dorothy Brown last night broadcast her campaign’s first Facebook Live video _____. *

Q.23
February 2019: Billionaire Joe Ricketts—patriarch of the family that owns the Chicago Cubs—is apologizing for “_____.” *

Q.24
February 2019: Even as he faces federal charges of shaking down _____, Ed Burke strolled to reelection in his Southwest Side ward. *

Q.25
March 2019: A Tribune editorial demands Cook County State’s Attorney Kim Foxx explain her office’s decision to drop all charges against _____. *

Q.26
April 2019: Gov. Pritzker is backing a referendum to let Illinoisans decide whether to overhaul the state’s _____. *

Q.27
May 2019: Continuing his farewell tour yesterday at a City Club of Chicago luncheon, Mayor Emanuel addressed criticism he’s been a lousy collaborator: “I am at fault for being _____.” *

Q.28
May 2019: A report in the scientific journal The Lancet Infectious Diseases nails Cook County as the most likely to suffer the next big _____ outbreak … partly because of those two major airports. *

Q.29
August 2019: Melania Trump tweeted a photo of herself and the president with a baby orphaned in the horrific attacks in El Paso—showing the president _____. *

Q.30
September 2019: Mayor Lightfoot minced no words in firing back at Texas Sen. Ted Cruz: “_____.” *

Q.31
November 2019: Several employees of a Buffalo Wild Wings restaurant in Naperville have been fired after a manager asked a party to move because a regular customer “doesn’t want _____.” *

Q.32
December 2019: Chicago magazine’s Kate Bernot surveys the role the city’s infamous Ceres Cafe, on the ground floor of the Board of Trade, played in the downfall of _____. *

Q.33
January 2020: President Trump seemingly declined House Speaker Nancy Pelosi’s handshake before his State of the Union address, and then—when he was done—she pointedly _____. *

Q.34
February 2020: A top member of President Trump’s coronavirus task force asked Twitter for help _____. *

Q.35
April 2020: A video call that included Chicago aldermen and state representatives was hijacked by someone streaming _____. *

Q.36
May 2020: Gov. Pritzker has forbidden _____ from joining his daily media briefings. *

Q.37
June 2020: Mayor Lightfoot pledges consequences for Chicago cops caught on surveillance video literally lying down on the job for hours—and snacking on popcorn—in _____ as violence swept the neighborhood. *

Q.38
August 2020: Wisconsin’s governor has written to President Trump, asking that he _____ violence-torn Kenosha. *

Q.39
September 2020: Flowers in memory of _____ have been accumulating at the North Side headquarters of the classical music record company founded by her son. *

Q.40
November 2020: Illinois’ governor yesterday turned—in the words of Playbook Illinois’ Shia Kapos—“as angry as your Playbook host has ever seen him” … to denounce … false and hateful rumors about _____. *

Q.41
January 2021: _____ runoff victories for Senate candidates Jon Ossoff and Raphael Warnock give the Democrats total control of Congress. *

Q.42
February 2021: Comedian, Trump critic and Oak Park native _____ has reported one of her social-media trolls to the FBI after spotting her in the Capitol riot. *

Q.43
February 2021: Illinois becomes first in the nation to abolish what critics have labeled a tax on the poor: _____. *

Q.44
May 2021: Female students at one of Chicago’s most celebrated high schools, _____, say it’s been an open secret for years that a coach and teacher was a guy to be avoided. *

Q.45
July 2021: The discovery of _____ in a hotel room overlooking a downtown Chicago beach is ratcheting up concern over hospitality industry security. *

Q.46
July 2021: An internal CDC presentation escalates concern about the coronavirus _____ variant, warning that it’s potentially as contagious as chickenpox and spreads more easily than smallpox, the common cold and the 1918 flu. *

Q.47
September 2021: The first Illinoisan to plead guilty in connection with the Jan. 6 insurrection at the Capitol … stipulated that he was “_____” as he threw a chair toward Capitol Police. *

Q.48
September 2021: Tonight could bring a vote by the Chicago Public Media board—which oversees WBEZ-FM—to combine its ownership with that of the _____. *

Q.49
December 2021: Citing death threats against his family, an Illinois lawmaker who’d proposed to make people who are willfully unvaccinated against COVID-19 pay their own health care costs has _____. *

Q.50
January 2022: Private health insurers will have to cover up to _____ home COVID-19 tests per month for their customers. *

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