Nikko D’Ambrosio, 32, of Des Plaines, Illinois, made headlines this week after being sentenced to one year in federal prison for tax fraud—a case involving alleged ties to Chicago mob figures and a notorious Facebook lawsuit. U.S. District Judge Thomas Durkin delivered the sentence, describing D’Ambrosio’s actions as “patently outrageous” for grossly underreporting income made from distributing gaming machines for Mac-T LLC, a company with reputed mob affiliations.
D’Ambrosio, who earned upwards of $300,000 from sweepstakes machine commissions in a single year, claimed only $4,000 in taxable income in his filings, falsely reporting extensive travel expenses and donations to evade nearly $119,000 in taxes. Judge Durkin highlighted the implausibility of D’Ambrosio’s claims, noting his purported mileage was “enough to drive to the moon and back.”
Despite D’Ambrosio’s defense team’s attempts to attribute the tax discrepancies to poor financial skills and a reliance on a relative for tax preparation, prosecutors argued D’Ambrosio had both motive and knowledge of the false returns. Assistant U.S. Attorney Richard Rothblatt remarked that D’Ambrosio had “119,000 reasons to lie,” emphasizing the clear incentive for fraud.
Meanwhile, D’Ambrosio gained additional media attention with a defamation lawsuit filed in January against Facebook and members of the Chicago-based “Are We Dating the Same Guy?” Facebook group. The group, designed to allow women to share experiences about dating men in the community, featured posts about D’Ambrosio that he claims were defamatory and harmful to his reputation.
One woman posted about her interactions with D’Ambrosio, describing him as “clingy” and warning others about his behavior, prompting further comments from other women recounting similar experiences. The lawsuit alleges that the group’s activity constituted defamation and invasion of privacy.
Despite his efforts to paint a different image during sentencing, additional information provided by the prosecution pointed to alleged harsh text messages D’Ambrosio sent to one of the women involved in the suit. Rothblatt claimed these messages reflected his true character, though D’Ambrosio’s lawyer, Christopher Grohman, dismissed the texts as a one-time lapse in judgment.
The case underscores a tumultuous year for D’Ambrosio, whose legal troubles now include both the criminal sentence for tax fraud and the ongoing defamation lawsuit against Facebook and its users. As D’Ambrosio’s one-year sentence begins, his legal battles continue, spotlighting the broader implications of social media defamation and income tax evasion.
