Chicago Slots Salesman Who Sued ‘Are We Dating the Same Guy?’ Imprisoned for Tax Evasion

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A Chicago-area sweepstakes-machine salesman who sued Facebook and dozens of women from the “Are We Dating the Same Guy?” (AWDTSG) Facebook group has been sentenced to 12 months in a federal prison for tax evasion.

Nikko D’Ambrosia, above, is suing almost 30 women in Facebook’s AWDTSG Chicago subgroup after they reported their negative dating experiences with him online. (Image: Facebook/Casino.org)

In a lawsuit filed in January, just days before his trial for falsifying his tax returns, Nikko D’Ambrosio, 32, claimed that he was defamed and that his privacy rights were violated by members of the group.

AWDTSG, which has millions of members worldwide, describes itself as a “red flag awareness group,” where users can share dating profiles of men and post warnings.

D’Ambrosio’s lawsuit made national headlines, but few column inches were devoted to his problems at the time with the IRS.

Employer’s Alleged Mob Ties

The salesman worked for electronic sweepstakes operator MAC-T. The company allegedly has links to Robert “Bobby” Dominic, a reputed Chicago Outfit associate, according to The Chicago Tribune.

MAC-T has also been tied by the Tribune to James Weiss, who was sentenced to five and a half years in prison in October 2023 for bribing two state lawmakers to back pro-sweepstakes legislation.

D’Ambrosio was convicted in January of two counts of making false statements on his personal income tax returns, in 2019 and 2020. The salesman claimed $4,443 as taxable income in 2019, while claiming expenses of $158,528. The following year, he claimed $14,874 as taxable and $252,625 in expenses.

These expenses included driving 474,000 miles on business trips and spending $263,000 on business-related meals. He also claimed to have donated $64,500 to St. John Cantius Church in Chicago, but the church had no record of such a donation.

To the Moon and Back

Sentencing, US District Judge Thomas Durkin noted the amount of travel miles D’Ambrosio claimed in two years would have “taken you to the moon and back,” which is the kind of line that might get you a red flag on AWDTSG.

“You lied badly,” the judge added.

In the AWDTSG lawsuit, D’Ambrosio is seeking more than $75,000, alleging his reputation was damaged and privacy violated after he was “doxed” by the Facebook group.

D’Ambrosio said he met the woman who first red-flagged him at an event in Chicago last year. They later went on a “handful of unremarkable dates” but “never engaged in an exclusive dating relationship,” according to the lawsuit.

‘Emotional Distress’

In November 2023, the woman posted on AWDISG about D’Ambrosio: “We met organically in Chicago two and a half years ago. Very clingy very fast. 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 post prompted several other women to come forward to report similarly negative experiences with him, including some who described him as a “psycho,” according to the suit.

D’Ambrosio claims the posts caused him “personal humiliation, mental anguish and suffering, emotional distress, stress, anxiety” and unspecified lost earnings.

“Our client’s a victim. He’s a victim on [sic] this matter,” his attorney, Marc Trent, said in January. “We want to stop there from being additional victims in the future.”

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