Chicago Slots Salesman Who Sued ‘Are We Dating the Same Guy?’ Imprisoned for Tax Evasion
Chicago Slots Salesman Who Sued ‘Are We Dating the Same Guy?’ Imprisoned for Tax Evasion
A Chicago-area sweepstakes-machine salesman, Nikko D’Ambrosio, has recently been sentenced to 12 months in federal prison following a conviction for tax evasion. This sentencing comes in the wake of a lawsuit he filed against Facebook and numerous individuals from the Facebook group “Are We Dating the Same Guy?” (AWDTSG).
In his lawsuit, filed shortly before a critical trial regarding his falsified tax returns, D’Ambrosio claimed he was defamed and that his privacy was violated by the group’s members. The AWDTSG group, which boasts millions of members globally, is identified as a “red flag awareness group,” providing a platform to share experiences and profiles of men, warning others about their behaviour.
Employer’s Alleged Connections to Organised Crime
D’Ambrosio worked for MAC-T, an electronic sweepstakes operator allegedly associated with Robert “Bobby” Dominic, a notable figure tied to the Chicago Outfit, as reported by The Chicago Tribune. MAC-T has also been linked to James Weiss, who received a five-and-a-half-year prison sentence in October 2023 for bribery related to pro-sweepstakes legislation.
D’Ambrosio was convicted in January of two counts of making false statements on his personal income tax returns for the years 2019 and 2020. For the year 2019, he reported a taxable income of $4,443 while stating $158,528 in expenses. In 2020, his reports claimed $14,874 in taxable income against expenses of $252,625.
Among his questionable expenses were claims of driving over 474,000 miles for business and spending over $263,000 on meals. He reportedly claimed to have donated $64,500 to St. John Cantius Church in Chicago, yet records from the church did not confirm this donation.
The Travel Claims that Raised Eyebrows
During the sentencing, U.S. District Judge Thomas Durkin quipped that the reported travel miles D’Ambrosio incurred in merely two years would likely have taken him “to the moon and back,” a comment that might create suspicion easily flagged by the AWDTSG group.
“You lied badly,” remarked the judge during the proceedings.
D’Ambrosio is pursuing over $75,000 in damages in his AWDTSG lawsuit, alleging that the Facebook group’s actions led to defamation and privacy violations, stemming from being “doxed” by its members.
He claimed he initially met the woman who reported him during a Chicago event last year. Despite having gone on several unsuccessful dates with her, he insists that there was never an exclusive relationship.
Claims of Emotional Distress
In November 2023, the initial complainant detailed her experience on AWDISG, describing D’Ambrosio as overly clingy, flaunting his wealth awkwardly, and expressing concern about discovering his “bad side,” particularly during business calls.
This post encouraged multiple women to share their own negative experiences with D’Ambrosio, with some branding him as a “psycho” in the process.
D’Ambrosio contends that these online posts induced significant “personal humiliation, mental anguish and suffering, emotional distress, and anxiety,” alongside unspecified lost earnings. His attorney, Marc Trent, has asserted that D’Ambrosio is a victim in this matter, stating, “We want to prevent other potential victims in the future.”
Conclusion
The bizarre intertwining of social media, personal relations, and the legal system in D’Ambrosio’s case raises vital questions about online harassment and the nuances of personal privacy. It also serves as a cautionary tale of how actions online can lead to serious legal repercussions. In an age where social platforms play a significant role in our personal lives, understanding the potential consequences of sharing experiences in groups like AWDTSG can be crucial.
As this situation unfolds, it is clear that both the public perception and personal implications can significantly impact individuals involved—whether they be victims or alleged perpetrators.
