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Local man who sued women over social media posts convicted of tax fraud

A Chicago-area man who made waves in national media when he filed a lawsuit against dozens of women who allegedly bad-mouthed him on a tell-all Facebook dating page was sentenced Wednesday to a year in prison for tax fraud that the judge had committed. called “patently scandalous”.

D’Ambrosio, 32, of Des Plaines, was convicted in January of tax fraud, alleging that he spent much of the income he earned distributing sweepstakes slot machines for a company linked to Chicago mafia figures. stated too low.

In handing down the sentence, U.S. District Judge Thomas Durkin said the figures D’Ambrosio tried to report to the IRS about his work miles, charitable contributions and business meals “are outrageous.”

“With the miles you said you drove, you could have driven to the moon and back,” Durkin said. The judge said he believed D’Ambrosio also lied when confronted by the FBI and that he committed perjury when he testified in his own defense.

“And you lied badly,” the judge said. “You doubled down.”

Durking also said that D’Ambrosio, according to presentation reports, told court officials he hoped for a presidential pardon in the future.

“The fact that you’re going to ask for a pardon is inexplicable to me,” Durkin said. “The regret seems to be more about the fact that I got caught than anything else.”

Before hearing the verdict, D’Ambrosio made a short statement to the court, asking for leniency and apologizing to his friends and family for what he had done to them.

“I’ve proven myself as a good family man,” D’Ambrosio said, sitting at the defense table in a black suit and white and black patterned tie. “I do go to church. I am true to my faith.”

D’Ambrosio was a small fish who got caught up in the same general investigation into the murky world of sweepstakes kiosks, an ongoing investigation that already brought down James Weiss, son-in-law of former Cook County Democratic boss Joe Berrios, and then-President has brought. – Illinois State Representative Luis Arroyo, in a scheme to bribe a senator to support sweepstakes legislation.

Earlier this month, Weiss’ brother Joseph pleaded guilty to lying to federal investigators about his brother’s alleged ties to the mafia, including his past dealings with infamous Outfit hitman Frank “The German” Schweihs and another unspecified said mafia associate.

According to trial testimony, D’Ambrosio’s boss Anthony DeMarco, of River Grove, who owns a company called Mac-T LLC, which specializes in sweepstakes machines, was the quasi-legal gambling kiosks that critics say were designed to circumvent city laws banning video poker.

The Tribune has previously reported that Mac-T also has ties to Weiss’s sweepstakes firm, as well as Robert “Bobby” Dominic, a reputed Chicago Outfit associate with longstanding ties to the mob’s Grand Avenue crew. Records obtained by the Tribune last year indicate that Dominic was a target of the investigation, although he has not been charged.

However, the jury in D’Ambrosio’s case did not hear any testimony about the Chicago Mafia or D’Ambrosio’s bizarre lawsuit, which was filed just days before he went on trial and named Facebook and more than two dozen women as defendants .

Instead, the case focused on D’Ambrosio’s 2019 and 2020 tax returns, in which he claimed only $4,000 in taxable income, even though he made more than $300,000 in one year alone from his cutting of the profits from the sweepstakes machines.

To lower his taxable income, D’Ambrosio reported spending hundreds of thousands of dollars taking liquor store and gas station owners out to dinner in an effort to get them to install Mac-T’s lottery kiosks in their businesses, according to the report. testimonials from the trial. .

D’Ambrosio also falsely claimed on tax returns that he had driven thousands of miles on business trips he never took, and that he had donated more than $70,000 to a local Catholic church, when in fact he had not donated a dime and not even a cent had donated. a parishioner, according to testimonies.

According to testimony, D’Ambrosio has paid a total of approximately $119,000 in income taxes over the past two years.

Testifying in his own defense, D’Ambrosio admitted on the witness stand that the returns were fake, but claimed he was bad at math and said he had placed all his trust in his cousin, a tax professional who prepared the documents and worked on the IRS submitted. .

To make their point, D’Ambrosio’s attorneys, Christopher Grohman and Ralph Meczyk, introduced into evidence their client’s rather mediocre grades in high school and community college. In his closing arguments Friday, Grohman told the jury that the case was not about greed: “It’s about stupidity.”

“I don’t mean this in any way to discredit Nikko, but as you can see from his educational records, he is not the most advanced human being,” Grohman told the jury. “Someone with his skills doesn’t do his own taxes, and frankly he shouldn’t. You go to a professional. And the professional he relied on was his cousin.”

In rebuttal, however, Assistant U.S. Attorney Richard Rothblatt said that D’Ambrosio was the only one who had the incentive to file a false return, and that “sometimes in life things are as simple as they seem .”

“This is a whodunnit without the mystery,” Rothblatt said. ‘This isn’t ‘The Usual Suspects’ with Keyser Soze and a fallen mug. … The defendant had 119,000 reasons to lie.”

While D’Ambrosio’s criminal case remained largely under the radar, the lawsuit he filed on January 8 made news in media across the country.

When his case went to trial in late January, jurors were asked if they had seen any of the stories, and two raised their hands, including one who was ultimately selected to sit on the panel.

The lawsuit alleges that D’Ambrosio was defamed and had his privacy rights violated after his name and photo were posted in 2023 to the Chicago chapter of a private Facebook group called “Are We Dating the Same Guy?”

The group gives women a platform to “discuss and discredit men in their local communities with whom they have allegedly had unsatisfactory dating experiences,” according to the lawsuit.

“The group pontificates to the world that they are doing ‘the Lord’s work’ by maintaining a platform where women can anonymously cast aspersions and attack the moral character of men they meet online,” the complaint says.

D’Ambrosio claimed he met the woman who first posted about him at an event in Chicago last year. They had consensual sex that same evening and later had “a handful” of “low-key” dates, but “never entered into an exclusive dating relationship.”

In November, the woman, under her own name, posted D’Ambrosio’s photo with a “red flag” warning to other women, saying, “We met organically two and a half years ago in Chicago.” Very sticky, very fast,” the suit said.

“I was showing off money very awkwardly and kept talking about how I didn’t want to see his bad side, especially when he was doing business,” the woman stated, according to the complaint, which includes a screenshot of the alleged comments.

The post led to a series of comments from other women claiming similar negative experiences with D’Ambrosio, the lawsuit alleged.

“A little over a year ago I went out with him a few times – he told me what I wanted to hear until I slept with him and then he ghosted. … I would stay away from it,” one woman commented, according to a screenshot attached to the filing.

D’Ambrosio’s attorneys argued at sentencing that despite the tax fraud, he is a person of strong moral character with a good support system of friends and family, and that he is a hard worker who is ready to move on his life.

In response, however, prosecutors turned over to the judge information they had gathered during an interview with the women D’Ambrosio had dated and who were named in the lawsuit, including a text message in which D’Ambrosio allegedly framed her threw the trash.

Rothblatt said the exchange showed that when D’Ambrosio thought no one was watching, “he could send cruel, demeaning and horrible messages to individuals.”

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