Chicago, Chicago, the crookedest town
Chicago, Chicago, I’ll show you around
You can spend your bottom dollar on an alderman in Chicago
The town Big Jim Thompson couldn’t shut down

On LaSalle Street, where pals meet to fix City Hall
They do things and accrue things the goo-goos appall
You’ll end up serving twenty to life
I heard a gov connive with his wife
In Chicago, Chicago, my hometown

1940 W. Foster Ave.: This long-abandoned police station was once the headquarters of the Summerdale District. In the late 1950s, eight Summerdale officers helped professional burglar Richard Morrison break into houses on the North Side. The cops not only acted as lookouts for Morrison, but helped him haul away the loot, then divided it up amongst themselves. Five cops went to prison. The scandal was so bad that Mayor Richard J. Daley had to hire an egghead professor to make the department look honest again. He fired police superintendent Timothy O’Connor, your usual Irish cop, and replaced him with reformer O.W. Wilson, dean of the University of California’s School of Criminology.

731 N. Wells St.: It’s now the Brehon Pub, but in 1977, it was the Mirage Tavern, a dive bar purchased by the Chicago Sun-Times and the Better Government Association for the purpose of catching city inspectors in bribe-taking mode. Reporters installed hidden cameras and recorded inspectors offering to overlook rats, maggots, loose electrical wires, a leaky ceiling and a trash-filled basement — for as little as ten bucks. After a 25-part series appeared in the Sun-Times, a dozen city officials were suspended or fired, and 18 electrical inspectors indicted. Mayor Michael Bilandic created an Office of Professional Review to end the grift. The Pulitzer committee refused to give the Sun-Times its big prize, saying there was “an element of entrapment” in buying a bar just to pay bribes. Is it really entrapment when the bribee asks for the cash?

Roosevelt Road and Kostner Avenue: The residents of North Lawndale hated the dump on this corner. They called it Mount Henry. It was piled six stories high with hazardous waste, which attracted rats and caused respiratory problems among its neighbors. The dump stayed in business, though. It was there to attract a species of pest almost as numerous as rats: corrupt aldermen. A sleazy FBI mole named John Christopher — felon, Mafia associate — bribed aldermen to allow him to dump at the site. He took 37th Ward Ald. Percy Giles to lunch at Edna’s, a now-closed soul food restaurant at 3175 W. Madison St. By the time the meal was finished, the alderman was $5,000 richer. Giles was convicted of corruption. So were aldermen Larry Bloom, Ambrosio Medrano, Allen Streeter, Jesse Evans, and Virgil Jones. Jones’s case was prosecuted by Lori Lightfoot, then with the U.S. Attorney’s Office. The other scandal: why one of the city’s poorest neighborhoods had to tolerate an illegal dump so prosecutors could notch convictions.

4060 S. Pulaski Road: This is a Burger King, but not just any Burger King. Ald. Edward Burke allegedly pressured its owners to do business with his real estate tax firm, in exchange for a remodeling permit. Federal prosecutors charged Burke with extortion in January 2019. He was forced to step down as chair of the Finance Committee. Mayoral candidate Lori Lightfoot seized on the scandal to promote herself as a reformer and win the election. Burke also won his election — to a 13th term as alderman of the 14th Ward. Like any good boss, he’s done a lot of favors for his constituents. This Burger King is also near the spot where Ofc. Jason Van Dyke shot and killed Laquan McDonald in 2014. Mayor Rahm Emanuel suppressed the police tape until after the 2015 election — but it’s a big reason he didn’t run for a third term. As we said, not just any Burger King. It’s the home of numerous whoppers told by politicians trying to get themselves out of trouble.

2869 S. Archer Ave.: When Patrick Daley Thompson needed a loan, he went to a bank in Bridgeport, the neighborhood where his family has lived and ruled for three generations. In 2011, Thompson began borrowing money from Washington Federal Bank for Savings, to remodel the Daley family bungalow at 3536 S. Lowe Ave. and a three-flat he owned, as well as to buy into a law firm partnership. Thompson never repaid the loans, even after receiving $1.5 million from the sale of an apartment building his father developed. (He used the money for a cottage in New Buffalo, where he could rub sun-screened elbows with other Daleys.) After the bank failed in 2017, federal regulators tried to collect on its debts. Thompson was convicted of trying to weasel out of payments by lying about how much he owed. Forced to give up his seat as 11th Ward alderman, he became another example of the third generation rule, which states that spoiled grandchildren squander the family legacy created by their ambitious grandparents.

2934 W. Sunnyside Ave.: At 6:15 on the morning of Dec. 9, 2008, FBI agents surrounded the Ravenswood Manor home of Gov. Rod Blagojevich. The feds had been listening in on Blago’s phone conversations for months. He was arrested for allegedly trying to sell the Senate seat occupied by Barack Obama, who had just been elected president. The governor was taken downtown and booked in his jogging suit. He was also charged with trying to extort a $50,000 campaign contribution from Lurie Children’s Hospital, 225 E. Chicago Ave. Blago was impeached by the legislature. In 2012, he was convicted and sentenced to 14 years in prison. President Donald Trump commuted Blago’s sentence in 2020. The ex-governor and ex-con returned home to Sunnyside Avenue, where he has filmed hundreds of Cameo greetings and scenes from his please-forgive-me documentary Being Blago.

42 W. Madison St.: As CEO of the Chicago Public Schools from 2012 to 2015, Barbara Byrd-Bennett occupied a top floor office at the district’s headquarters. Byrd-Bennett isn’t even from Chicago — she grew up in New York City, and ran the schools in Cleveland — but her term ended in the most Chicago Way imaginable: she was convicted of taking a 10 percent kickback from a $20.5 million no-bid contract to SUPES Academy, for which she once worked as a consultant. A lifetime of working in education made her a quick learner, obviously.

6500 S. Pulaski Road: For half a century, Michael Madigan has lorded over the 13th Ward Regular Democratic Organization from this three-story building in West Lawn, where the last machine boss meets each Saturday morning with his precinct captains. Despite practicing a brand of politics that has sent dozens of lesser legislators to prison, Madigan always managed to stay on the right side of the law — until 2020, when the feds charged the head of “the Madigan Enterprise” with 22 counts of bribery, racketeering, wire fraud, and extortion. As Speaker of the state house, he allegedly advanced ComEd’s interests in the legislature in exchange for no-show jobs for his friends, and pressured a contractor into doing business with his real estate law firm in exchange for a zoning approval. (See also: Ed Burke.) Madigan lost his speakership and resigned from the House — but he’s still 13rd Ward committeeman.

2200 Euclid Ave., Arlington Heights: In Illinois, bribery is just the cost of doing business, right? That’s what Marjorie Lindheimer Everett, owner of Arlington Park racetrack, thought. In 1961, Everett offered discounted stock options in the track to Gov. Otto Kerner. In exchange, she got choice racing dates. Kerner sold the stock at a profit in 1968. The next year, Everett deducted the stock’s value from her 1969 income tax, as a business expense. Federal officials detected a bribe. Kerner, by then a federal judge, was convicted and imprisoned by U.S. Attorney James R. Thompson. Thompson would go on to serve as governor for 14 years, without once going to prison — an Illinois record.

McCook: McCook has a population of only 249 people, but has nonetheless played a special role in the annals of Illinois corruption. It was the site of a Secretary of State’s drivers’ licensing facility where 80 truckers paid bribes for licenses — including Ricardo Guzman, who caused an accident that burned six children to death. The facility’s managers spent the bribes on tickets to fundraisers for their boss, George Ryan. The scandal would end Ryan’s governorship after one term, and lead to a five-year stretch in the federal pen in Terre Haute, Indiana.