When ATF agents and Chicago police arrested 45th Ward boss Charles Sikanich on Monday, police records state, Sikanich made one request over and over: Let me contact Ald. Jim Gardiner, he said, before you put me in custody.

The request went apparently unfulfilled. The next day, Sikanich — ward superintendent and Gardiner’s right-hand man — was in Cook County court on charges including gun possession and official misconduct. Two years ago, prosecutors said, he tried to sell an antique machine gun to an undercover ATF agent while he was on the clock for his Streets and Sanitation job.

It was the latest development in a rollercoaster year for the Northwest Side ward. Gardiner has been under federal criminal investigation for months relating to his conduct in office. He and Sikanich are being sued for allegedly having a man harassed, intimidated and ultimately falsely arrested. And Gardiner came under heavy public fire last year for profane and misogynist texts published by an anonymous online group.

Sikanich was ordered held in lieu of $100,000 bond after a brief hearing Tuesday. He was still in custody as of early Tuesday evening, according to the sheriff’s office.

The matter dates to February 2020, when the ATF got a tip from a confidential informant that Sikanich owned an MP 40 machine gun and was interested in selling it, Assistant Attorney General Jonas Harger said in court Tuesday. Sikanich asked the informant to find him a buyer, Harger said.

In May of that year, Sikanich met with the informant and an undercover ATF agent, and they tried to negotiate a selling price, authorities said. Agents staking out the meeting saw Sikanich arrive in his Department of Streets and Sanitation vehicle, prosecutors said. And time sheet records show he was on the clock at his city job during the time he allegedly was set to discuss the gun’s sale, Harger said in court.

A news release from Attorney General Kwame Raoul’s office also alleged that during the meeting, Sikanich “indicated he would have his mother complete the illegal transaction, as he hoped to avoid complications to his role as a superintendent of Chicago’s 45th Ward.”

More than a year later, in August 2021, federal agents confronted Sikanich, who led them to a “secret compartment” in his basement where a black duffel bag containing the gun was recovered, Harger said.

Sikanich’s attorney, Blaire Dalton, said in court the gun was a family heirloom, passed down from Sikanich’s grandfather. It dates from World War II’s Battle of the Bulge, Dalton said. The gun was “plugged” with lead and unusable, she said in court, noting that the gun was seized in August but Sikanich was only charged this month.

In response, Harger noted that it took the ATF less than an hour to render the gun usable, and it was still capable of firing shots. Sikanich “knew the gun was illegal and intended to sell it for an increased price because of illegality of the gun,” he said.

The $100,000 bond set by Judge Barbara Dawkins is higher than the $75,000 that prosecutors had requested, and significantly greater than the $500 that Sikanich’s attorney said he could pay.

In a news release Tuesday, Raoul stated that trying to sell a machine gun “demonstrates at best indifference toward the public’s safety. However, to do so on government time using government property demonstrates a shocking disregard for the people government employees have committed to serve.”

Asked about Sikanich’s arrest, a Streets and Sanitation spokeswoman said the department would not comment on a personnel issue.

Gardiner is also being sued for for allegedly violating the First Amendment rights of ward residents who were critical of him on social media by deleting their comments from his official Facebook page and blocking them from posting in the future.

Gardiner could not immediately be reached for comment Tuesday on the charges against Sikanich.

The freshman alderman has been a lightning rod for controversy during his first term representing parts of Jefferson Park, Portage Park, Old Irving Park and Norwood Park.

He rose in council chambers during the body’s September meeting to apologize after an anonymous Northwest Side online group published texts he sent a ward employee in which he referred to one City Council colleague as “a bitch” and the top aide of another council member as “his bitch,” and also used the term to describe a political communications consultant.

He said he was sorry for his “offensive words” but said he “never acted on any of those rants” in published texts in which he appeared to call for ward services to be withheld from political opponents.

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