CHICAGO— One of the most powerful and longest-serving City Council members in Chicago history appeared in federal court Thursday on a charge that he tried to shake down a major fast-food restaurant chain seeking city remodeling permits.

Alderman Ed Burke, 75, is charged with one count of attempted extortion for conveying to company executives in 2017 that they’d get the permits only if they signed on as clients at Burke’s private property-tax law firm in Chicago, a 37-page complaint unsealed on Thursday says.

For many Chicagoans suspicious of dealings behind closed doors at City Hall, Burke has personified the city’s machine politics for decades. Dozens of aldermen have entered U.S. District court on corruption charges, but Burke seemed too powerful, too wealthy and too savvy to land himself in the kind of legal trouble he now faces.

He sat in a packed Chicago federal courtroom Thursday afternoon with his arms folded, wearing his trademark pinstriped suit with a pocket square. Minutes later, he stood before U.S. Magistrate Sheila Finnegan, who asked if he understood the charge and that a conviction carried a lengthy prison sentence.

“Yes, your honor,” he answered calmly.

Prosecutors told the judge that Burke, who has publicly opposed the National Rifle Association and proposed multiple gun-control ordinances over the years, had 23 guns at his offices alone. The judge said one condition of his continued release is that he gets rid of all his guns, including any at his home. He also was required to turn over his passport.

The Democrat’s law firm, Klafter & Burke, represented the high-rise tower that bears President Donald Trump’s name. There’s no indication the case is at all tied to his firm’s work for Trump.

He’s been on the council for 50 years and for three decades has chaired its finance committee, which makes key decisions about how the city’s budget is spent.

A message seeking comment left at Burke’s law office was not returned. Burke said after FBI raids on his offices at City Hall and in his Southwest Side ward in November that he was sure agents wouldn’t find anything “amiss.”

Charges were filed in a complaint on Wednesday but only unsealed Thursday. A grand jury could still hand down a formal indictment, possibly adding new charges.

The complaint, which does not identify the fast-food company or the executives allegedly squeezed, includes excerpts from wiretaps of Burke’s phone and emails seized in the raids.

When the executives didn’t give Burke’s law firm the business he wanted, Burke spoke with one of his ward employees about how they would “play hard” ball with the company, the complaint says.

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