Local man who sued women over dating reviews convicted of tax fraud involving mob-connected business

Chicago-area native Nikko D’Ambrosio made a national media splash earlier this month when he filed a lawsuit against dozens of women who allegedly bad-mouthed him on a tell-all Facebook dating page, describing him as “clingy,” a ghoster and a show-off with money.

Turns out D’Ambrosio’s dating reviews were the least of his worries.

On Friday, D’Ambrosio, 32, of Des Plaines, was convicted in the same federal courthouse where his lawsuit is pending of tax fraud counts alleging he vastly underreported income he’d made distributing “sweepstakes” gaming machines for a company with ties to Chicago mob figures.

After a four-day trial, the jury deliberated less than 90 minutes before convicting D’Ambrosio on two counts of filing a false tax return, which each carry a maximum prison term of up to three years.

Dressed in a dark suit, D’Ambrosio sat up straight in his chair but showed no reaction as the verdict was read. U.S. District Judge Thomas Durkin set sentencing for May 28.

D’Ambrosio was a small fish ensnared in the same overall investigation into the shady world of sweepstakes kiosks, an ongoing probe that already has brought down James Weiss, son-in-law of former Cook County Democratic boss Joe Berrios, as well as then-Illinois state Rep. Luis Arroyo, in a scheme to bribe a state senator to support sweepstakes legislation.

In August, prosecutors charged Weiss’ brother, Joseph, with lying to federal investigators about his brother’s reputed mob ties, including his previous contacts with infamous Outfit hit man Frank “The German” Schweihs and another, unnamed mob associate.

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

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

The jury in D’Ambrosio’s case, however, did not hear any testimony about the Chicago mob 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, where he claimed as little as $4,000 in taxable income, even though he made more than $300,000 in one year alone from his cut of the sweepstakes machines profits.

To reduce his taxable income, D’Ambrosio reported he’d spent hundreds of thousands of dollars taking liquor store and gas stations owners out to dinner in an effort to get them to place Mac-T’s sweepstakes kiosks in their businesses, according to trial testimony.

D’Ambrosio also falsely claimed on the tax filings that he drove thousands of miles on business-related trips he never took, and donated more than $70,000 to a local Catholic church when in fact he’d donated not a penny and wasn’t even a parishioner, according to testimony.

In all, D’Ambrosio skipped out on paying about $119,000 income taxes over the two years, according to testimony.

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

To help bolster their point, D’Ambrosio’s attorneys, Christopher Grohman and Ralph Meczyk, submitted their client’s rather lackluster high school and community college grades as evidence. In his closing argument Friday, Grohman told the jury the case was not about greed, “It’s about stupidity.”

“I don’t mean this to disparage Nikko in any way, but as you can see from his educational records, he is not the most sophisticated human being,” Grohman told the jury. “Somebody with his skill set is not doing his own taxes, and nor should he be, frankly. You go to a professional. And the professional he relied upon was his cousin.”

In rebuttal, however, Assistant U.S. Attorney Richard Rothblatt said 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 a whodunit without the mystery,” Rothblatt said. “This isn’t ‘The Usual Suspects’ with Keyser Soze and a dropped mug. … The defendant had 119,000 reasons to lie.”

The Tribune has previously reported that Mac-T LLC, was organized by DeMarco in 2014 and was registered to the same address on Sibley Boulevard in Dolton where Weiss also listed some of his businesses.

DeMarco originally incorporated Mac-T using an address of 723 W. Grand Ave. in Chicago, which is a single-room occupancy hotel in the same building that houses the Italian restaurant La Scarola and Richard’s Bar, which on paper is owned by Dominic’s sister.

According to FBI and Chicago records, Dominic ran pornography and gambling interests for the Grand Avenue crew, which was headed by legendary mobster Joseph “The Clown” Lombardo.

While D’Ambrosio’s criminal case flew largely under the radar, the lawsuit he filed Jan. 8 made news in outlets around the country.

When his case went to trial on Tuesday, 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 suit, which seeks class-action status, alleges D’Ambrosio was defamed and his privacy rights were violated after his name and photo were posted in 2023 in the Chicago chapter of a private Facebook group called “Are We Dating the Same Guy?”

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

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“The group pontificates to the world that they are doing ‘the Lord’s work’ by maintaining a platform to permit women to anonymously dox defame and attack the moral character of men they met online,” the suit states.

D’Ambrosio alleged he’d met the woman who first posted about him at an event in Chicago last year. They had consensual sex that same night and later went on “a handful” of “unremarkable” dates, but “never engaged in an exclusive dating relationship.”

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

“Flaunted money very awkwardly and kept talking about how I don’t want to see his bad side, especially when he was on business calls,” the woman stated, according to the suit, which included a screen shot of the alleged comments.

The posting led to a series of comments from other women claiming similarly negative experiences with D’Ambrosio, the suit alleged.

“I went out with him a few times just over a year ago — he told me what I wanted to hear until I slept with him and then he ghosted. … I’d steer clear,” one woman commented, according to a screenshot included in the filing.


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