Facebook Drama Lands Sweepstakes Salesman in Tax Evasion Turmoil


In an intriguing twist to a tale of modern-day romance gone awry, Nikko D’Ambrosio, a sweepstakes-machine salesman from the Chicago area, has found himself at the wrong end of justice after tangling with the Internal Revenue Service (IRS) and a group of women from Facebook’s controversial “Are We Dating the Same Guy?” (AWDTSG) forum. D’Ambrosio has been sentenced to a one-year federal prison stint for committing tax evasion.

The 32-year old D’Ambrosio made an audacious legal move when he chose to sue nearly 30 women, all members of the Chicago subgroup of the massive AWDTSG Facebook collective for unfairly tarnishing him on the public platform. The group, which boasts an international member base in the millions, is widely known as an arena where women can congregate to share experiences about less-than-stellar dating prospects, often presenting ‘red-flag’ warnings on potential suitors.

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The lawsuit, filed by D’Ambrosio just mere days before his tax evasion trial was set to start, stemmed from the claim that his privacy was infringed and his reputation defamed by these women.

Simultaneous to the lawsuit hullaballoo, D’Ambrosio’s professional life was under significant scrutiny as well. His association with MAC-T, an electronic sweepstakes operator, brought him into proximity with dubious figures like Robert “Bobby” Dominic, an alleged associate of the notorious Chicago Outfit, and James Weiss, who was recently put behind bars for bribery. Weiss had been implicated in bribing state lawmakers in return for favorable legislation.

As D’Ambrosio’s reputation on AWDTSG hovered under a cloud of suspicion, his financial dealings began to unravel. Convicted on the grounds of falsifying his personal income tax returns for 2019 and 2020, D’Ambrosio had reported taxable income far less than his extravagant declared expenses. Claiming to have traveled an incredible 474,000 miles for business trips in two short years and expensed an eye-watering $263,000 on work-related meals raised egregious red flags with the IRS. The most egregious of these offenses, perhaps, was his claim to have donated a substantial $64,500 to a Chicago church which had no record of the supposed generous donation.

D’Ambrosio drew severe criticism from the presiding US District Judge Thomas Durkin. As a snub to his ludicrous travel miles claim, Durkin quipped that such an astronomical number would have taken him ‘to the moon and back’ – a clear colloquial hint at the surreality of D’Ambrosio’s assertion. Durkin further remarked, quite succinctly, that D’Ambrosio had “lied badly”.

D’Ambrosio, undeterred by his legal and financial woes, continues his legal battle against the Facebook group AWDTSG, asserting that his reputation was tarnished, and his privacy ousted without just cause, seeking monetary damages in excess of $75,000.

Portraying himself as the victim, D’Ambrosio insists that the relationship with the woman who first raised the red flag was not exclusive but was just a series of mundane dates. His attorney, Marc Trent, aligns with this interpretation, declaring that D’Ambrosio was unfairly singled out, and they aim to prevent any such future victimization.

The eventual resolution to D’Ambrosio’s predicament remains uncertain, yet the circumstances surrounding his saga have certainly grabbed national attention, shedding light on the intersection of law enforcement, digital dating, and personal reputation management.