Corrupt businessman's partner pleads guilty to prostitution conspiracy

Iman Bambooyani admitted to jet-setting across the country with four women and paying them thousands of dollars for sex. He’s now agreed to cooperate with federal prosecutors.

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Iman Bambooyani leaves the Dirksen Federal Courthouse in ChicagoIman Bambooyani leaves the Dirksen Federal Courthouse after pleading guilty to a prostitution conspiracy June 18, 2024.

Iman Bambooyani leaves the Dirksen Federal Courthouse Tuesday after pleading guilty to a prostitution conspiracy.

Anthony Vazquez/Sun-Times

An associate of a clout-heavy Chicago businessman serving time for bribery pleaded guilty Tuesday to a sex-crime charge leveled amid federal investigations of organized crime, gambling and corruption.

Iman Bambooyani, 43, faces more than a year in prison under federal guidelines now that he’s admitted to a prostitution conspiracy. A grand jury indicted Bambooyani and Hojat “Grandpa” Askari in May 2023.

But Bambooyani also agreed Tuesday to cooperate with prosecutors — which could get him a break on his sentence. U.S. District Judge Martha Pacold agreed to put his sentencing on hold until that cooperation is complete.

The charges against the two men have been linked to the case against Joseph Weiss, who pleaded guilty in May to lying to federal investigators. He’s the brother of James Weiss, who is already serving a 5½-year prison sentence for bribing two Illinois lawmakers in a separate matter.

Bambooyani and James Weiss are business partners, records show. Askari is identified in court records as an Arizona doctor specializing in internal medicine. He has pleaded not guilty and is set for trial in April 2025.

The charges against the Weiss brothers revolved around their involvement in the sweepstakes gambling machine business. The machines look like traditional video gaming devices but operate in a way that puts them beyond the reach of Illinois’ video gaming laws.

The FBI and IRS investigated possible mob ties to the machines, including an alleged association between James Weiss and the late mobster Frank “The German” Schweihs. The investigation also led to a tax-evasion conviction and one-year prison sentence for Nikko D’Ambrosio of Des Plaines, who also was involved with sweepstakes machines.

Though the case against Bambooyani and Askari has been linked to the same investigation, the two men are accused of jet-setting across the country with four women and paying them thousands of dollars for sex.

An FBI affidavit obtained by the Chicago Sun-Times details four trips involving Bambooyani, Askari and two of the unnamed women. They traveled to Walt Disney World, Las Vegas and Arizona in 2018, it said. Investigators interviewed the two women and said one of them referred to Askari as “grandpa” because he was about 25 years older than she is.

One of the two women told authorities they received “several thousand dollars” in cash to split during the Disney World trip, and that it was her understanding they were paid because they had sex with the men. One woman deposited $4,500 in cash in her bank account, and the other deposited $1,595, according to the affidavit.

After the trip to Las Vegas, one woman deposited $1,750 in cash, and the other deposited $3,106. One of the women said she understood the money came from Askari to pay for sex acts.

Following two trips to Arizona, one of the women deposited $4,082 and then $3,300 into her checking account, according to the affidavit.

One woman recalled consuming alcohol, lorazepam, cocaine and codeine while traveling with Bambooyani, records show. Later, in 2019 and 2020, the women sent text messages to each other about their travels with the men.

“Is it weird that seems like it never happened?” one of the women asked the other.

“No not at all I’ve completely blocked it out too,” the other replied. “Plus we were on Xanax codeine and god knows what else lol.”

“The codeine oh my god,” the first woman responded.

The affidavit also documents an apparent suicide attempt by one of the women in 2020.

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