Nikko D’Ambrosio. (Photo from D’Ambrosio’s 2023 civil court lawsuit)

A Des Plaines “sweepstakes” kiosk salesman who claimed enough mileage “to drive to the moon and back” on two years of tax returns, was sentenced to one year and a day in federal prison May 29.  

Nikko D’Ambrosio, 32, a salesman for an Illinois-based electronic kiosk operator, claimed to have driven more than 474,000 miles on business-related travel in 2019 and 2020, and to have spent more than $263,000 in business-related meals in that period. D’Ambrosio also falsely claimed to have donated $63,000 to a local Catholic Church.  

Under federal sentencing guidelines, D’Ambrosio will serve approximately 10 months in prison. Government prosecutors had asked for a sentence of 27-33 months. 

At sentencing, Judge Thomas Durkin called D’Ambrosio’s claimed deductions “patently outrageous,” and noted that such mileage “would have allowed you to drive to the moon and back.”  

On his 2019 tax return, D’Ambrosio reported $213,185 in gross income, which his claimed business expenses reduced to a mere $4,443 in net taxable income. That included $122,169 in vehicle expenses, a $32,094 deduction based on a claimed $64,189 spent on business meals, and a $26,751 deduction based on $29,775 purportedly donated to St. John Cantius Church in Chicago 

D’Ambrosio’s 2020 tax deductions were even greater; a mileage deduction of $152,170 based on a claimed 264,673 business miles driven; a $99,806 deduction based on claimed meal expenses of $199,612, and $37,749 deduction based on $34,725 in claimed 2020 charitable contributions. Those fraudulent deductions helped bring down D’Ambrosio’s 2020 gross income of $334,210 to just $14,874 in net taxable income.  

Unfortunately for D’Ambrosio, available documentation refuted, rather than supported, his deductions. The business manager at St. John Cantius Church testified D’Ambrosio was not a registered parishioner at the church in 2019 or 2020 and that there was no record of any charitable contributions from defendant in those years. 

At trial, prosecutors introduced bank statements and credit card records showing that D’Ambrosio “could not possibly have spent $64,189 on business meals in 2019 or $199,612 in 2020.” They also introduced records from the Illinois Secretary of State, the Illinois EPA and personal vehicle maintenance records showing that he “did not drive anywhere close to 210,637 miles in 2019, or 264,673 miles in 2020 (let alone for business purposes).” 

D’Ambrosio’s lawyers told the court that “stupity, not greed” was responsible for the figures D’Ambrosio used, and that he is “an individual who has struggled with intellectual challenges throughout his life.” Among those challenges, they suggested, were “neuro-developmental issues.” 

The defense attempted to place to bulk of the responsibility for D’Ambrosio’s wildly improbable claims for mileage and meal expenses on his cousin, who works for the IRS. That cousin, they argued, assisted him in compiling the figures on a worksheet used to prepare his tax filings.  

“(D)espite being highly educated in this field, (D’Ambrosio’s cousin) did not seem to notice that the mileage deductions equaled twice the distance to the moon and back (sic) or that the business meals expenses would have been the equivalent of nightly reservations for one of Alinea’s first-floor gallery tables,” his attorneys said.  

“A more plausible explanation would be that one cousin reached out to the other cousin, and the cousin that both works for the IRS and has prepared the other cousin’s tax returns for years, told the tax-filing cousin that he can claim whatever bogus deductions he wants and the chances of him getting caught are negligibly low.” 

D’Ambrosio’s problems do not appear to be over. Prosecutors told the court that he did not file a tax return in 2021 or 2022, during which time he had gross income of $870,671. Altogether, the government contends, D’Ambrosio owes $517,000 in income taxes, penalties and interest.  

In their sentencing memo seeking probation for D’Ambrosio, his lawyers alluded to his current civil lawsuit against the parent company of Facebook and some 26 women he alleges defamed him in 2023 with negative comments about him on a private Facebook group called “Are We Dating the Same Guy?” 

“Aside from the (criminal) offense, Mr. D’Ambrosio is someone who has tried to work hard (and) be kind,” his attorney wrote, then alluding to D’Ambrosio’s civil suit, saying, “arguably except to the occasional dating prospect …”