Chicago-based Slots Salesman Sued for Asking "Are We Dating the Same Guy?" Faces Jail Time for Tax Fraud
Chicago-based sweepstakes-machine salesman, Nikko D'Ambrosio, who filed a lawsuit against Facebook and numerous members of the "Are We Dating the Same Guy?" group, was recently ordered to spend a year in federal custody for tax evasion crimes.
The lawsuit against the social media giants and the group's members was filed in January, just before his trial for tax fraud. The salesman accused them of defaming him and infringing on his privacy rights.
AWDTSG, a massive Facebook community boasting millions of users globally, styles itself as a "red flag awareness group" where people can share dating profiles and post warnings about men with unsavory pasts.
The media generally ignored D'Ambrosio's financial troubles with the IRS during the uproar over the lawsuit.
A Troubling Association
D'Ambrosio was an employee of MAC-T, a sweepstakes operator with alleged connections to Bobbie Dominic, a suspected member of the Chicago Outfit, a criminal organization. MAC-T has also been linked to James Weiss, who in October 2023 was sentenced to five and a half years in prison for paying off two state lawmakers to support legislation favoring the company.
D'Ambrosio was charged with two counts of filing false tax returns in 2019 and 2020. He reported $4,443 in taxable income in 2019 while notching up expenses of $158,528. In the following year, he declared $14,874 as taxable income alongside $252,625 in expenses.
These expenses included racking up 474,000 miles on business trips and spending $263,000 on business-related meals. He claimed donating $64,500 to the St. John Cantius Church in Chicago, but the church had no record of such a donation.
A Galaxy of Lies
During sentencing, Judge Thomas Durkin commented that the 474,000 miles D'Ambrosio purportedly drove in two years was "enough to take you to the moon and back," potentially drawing even more flags by group members.
"You lied badly," the judge added.
In his lawsuit against the AWDTSG members, he's demanding $75,000 in compensation, alleging his reputation and privacy were marred once he was "doxed" by the Facebook group. He argued that he only met the woman who first brought the danger signal to his attention at a 2022 Chicago event. The pair had a handful of "unremarkable dates" but never engaged in an exclusive relationship, according to the complaint.
'Parallel Distress'
Following his 2023 Chicago event encounter, a woman commented on the group 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 comment lead to other women sharing their negative experiences with him, leading to one woman calling him "a psycho," per the suit.
D'Ambrosio holds that the posts have caused him "personal humiliation, mental anguish and suffering," emotional distress, anxiety, stress, and unspecified financial losses.
"My client's a victim in this case," his attorney, Marc Trent, shared in January. "We're aiming to prevent more victims from arising in the future."
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