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

A Chicago-area man who caused a national media sensation by filing a lawsuit against dozens of women who allegedly reported him on a tell-all Facebook dating page was sentenced Wednesday to a year in federal prison for fraud tax that the judge described as “manifestly scandalous”.

D'Ambrosio, 32, of Des Plaines, was convicted in January of tax fraud, alleging he grossly understated the income he earned distributing slot machines for a company with ties to Chicago mafia figures.

In handing down his sentence, U.S. District Judge Thomas Durkin said the numbers D'Ambrosio attempted to report to the IRS regarding his business mileage, charitable contributions and business meals were “outrageous.”

“The miles you said you traveled would have taken you to the Moon and back,” Durkin said. The judge said he believed D'Ambrosio also lied when confronted by the FBI and perjured himself when he testified in his own defense.

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

Durking also mentioned that, according to presentencing reports, D'Ambrosio told court officials he hoped for a presidential pardon in the future.

“The fact that you are asking for forgiveness, I find inexplicable,” Durkin said. “The remorse seems to come more from getting caught than anything else.”

Before learning of the sentence, D'Ambrosio made a brief statement to the court asking for leniency and apologizing to his friends and family for what he put them through.

“I've established myself as a good family man,” D'Ambrosio said, sitting at the defense table, wearing a black suit and white and black patterned tie. “I go to church. I am faithful to my faith.

D'Ambrosio was a small fish caught in the same overarching investigation into the shady world of sweepstakes booths, an ongoing probe that has already brought down James Weiss, son-in-law of Cook County's former Democratic boss, Joe Berrios, along with -Illinois State Representative Luis Arroyo in a scheme to bribe a state 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 prior contacts with the infamous Outfit hitman Frank “The German” Schweihs and another anonymous mob associate.

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

The Tribune previously reported that Mac-T also had ties to Weiss's sweepstakes company, as well as Robert “Bobby” Dominic, a noted Chicago Outfit associate with longtime ties to the team. the Grand Avenue Mafia. Records obtained by the Tribune last year show Dominic was a target of the investigation, although he was not charged.

The jury in D'Ambrosio's case, however, heard no testimony about the Chicago Mafia or D'Ambrosio's bizarre lawsuit, which was filed just days before his trial and named Facebook and more than two dozens of women as defendants.

Instead, the case focused on D'Ambrosio's tax returns for 2019 and 2020, in which he claimed only $4,000 in taxable income, even though he earned more than $300 $000 in just one year thanks to his share of the profits from the sweepstakes machines.

To reduce his taxable income, D'Ambrosio said he spent hundreds of thousands of dollars taking liquor store and gas station owners out to dinner in an effort to get them to place the raffle kiosks. fate of Mac-T in their businesses, according to trial testimony. .

D'Ambrosio also falsely claimed on his tax returns that he traveled thousands of miles on business trips he never took and that he donated more than $70,000 to a local Catholic church when in reality he had not given a cent and had not even given a penny. a parishioner, according to testimony.

In total, D'Ambrosio failed to pay about $119,000 in income taxes over the two years, according to testimony.

Testifying in his own defense, D'Ambrosio admitted on the witness stand that the statements were false, but claimed to be bad at math and said he placed all his trust in his cousin, a tax professional who prepared and submitted documents to the IRS. .

To help buttress their argument, D'Ambrosio's attorneys, Christopher Grohman and Ralph Meczyk, presented as evidence their client's rather poor grades in high school and community colleges. In his closing argument Friday, Grohman told the jury the case wasn't about greed, “it's about stupidity.”

“I don't want to disparage Nikko in any way, but as you can see from his academic record, he's not the most sophisticated human being,” Grohman told the jury. “Someone with his skills doesn't do their own taxes, nor should they, frankly. You go to a professional. And the professional he relied on was his cousin.

However, in rebuttal, Assistant U.S. Attorney Richard Rothblatt said D'Ambrosio was the only one induced to file a false statement and that “sometimes in life, things are as simple as they make themselves appear.”

“It’s a whodunnit without a mystery,” Rothblatt said. “It's not 'The Usual Suspects' with Keyser Soze and a dropped mug. … The accused had 119,000 reasons to lie.

While D'Ambrosio's criminal case has gone largely unnoticed, the lawsuit he filed on Jan. 8 made headlines 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 of them raised their hands, including one who was ultimately selected to serve on the jury.

The suit alleges that D'Ambrosio was defamed and his privacy rights were violated after his name and photo were published in 2023 in the Chicago section of a private Facebook group called “Let's Date the same guy?

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

“The group pontificates to the world that it is doing 'the Lord's work' by maintaining a platform for women to anonymously defame and attack the moral character of men they have met online,” the lawsuit states .

D'Ambrosio claimed he met the woman who first posted about him at an event in Chicago last year. They had consensual sex the same night and subsequently went on “a handful” of “mundane” dates, but “never engaged in an exclusive romantic relationship.”

In November, the woman, using her own name, posted D'Ambrosio's photo as a “red flag” to other women, saying, “We met organically in Chicago two and a half years ago . Very sticky very quickly,” according to the suit.

“I displayed money in a very awkward manner and kept saying I didn't want to see his bad side, especially when he was on a business call,” the woman said, according to the complaint, which included a screenshot of the alleged comments.

The post led to a series of comments from other women claiming similarly negative experiences with D'Ambrosio, according to the suit.

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

D'Ambrosio's attorneys argued during sentencing that despite the tax evasion, he is a person of strong moral character with a good support system of friends and family and a hard worker willing to advance in his life.

In response, however, prosecutors handed the judge information they had gathered during an interview with the women D'Ambrosio had dated and who were named in the lawsuit, including an exchange of text messages during from which D'Ambrosio allegedly trashed it.

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

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