Politically connected businessman pleads guilty to arranging sexual encounters

A Chicago entrepreneur with business ties to the son-in-law of former Cook County Democratic boss Joseph Berrios pleaded guilty Tuesday to federal charges alleging he arranged to have women travel out of state for high-paid trysts with himself and others.
Iman Bambooyani, 43, who calls himself “The Wolf of Rush Street” on social media, entered his plea to a conspiracy count during a hearing before U.S. District Judge Martha Pacold. Preliminary sentencing guidelines call for up to a year and a half in prison. A sentencing date was not immediately set.
Bambooyani’s plea agreement with prosecutors revealed that he is cooperating with the government in the hopes of getting a break on his sentence.
His attorney, Josh Adams, declined to comment Tuesday. Bambooyani, dressed in a dark gray suit and pink shirt, also did not speak to reporters on his way out of the Dirksen U.S. Courthouse.
A flashy, politically connected businessman who has dabbled in everything from valet parking to restaurants, real estate, wind farms and telemedicine, Bambooyani has long-standing business ties to James Weiss, who was convicted last year of conspiring to pay off two sitting state legislators to support legislation expanding the use of so-called sweepstakes gaming machines.
Weiss, who is married to Berrios’ daughter, former state Rep. Maria “Toni” Berrios, was sentenced in October to 5 1/2 years in prison.
In addition to once running the Cook County Democratic Party, Joe Berrios was also Cook County Assessor from 2010 to 2018.
Bambooyani was quietly charged in May 2023 along with Dr. Hojat Askari, of Prescott, Arizona, nicknamed “Grandpa,” who was accused of paying Bambooyani tens of thousands of dollars in 2018 to finance the women’s travel and other expenses. Askari also was charged with lying to FBI agents when he denied having met the women for sex.
Bambooyani admitted in his plea agreement that between January and May 2018, he arranged for four women — two from Miami and two from Chicago — to travel to various states to have sex in exchange for money with Bambooyani, Askari and a business associate of theirs, identified only as “Individual A,” as well as others.
In addition to paying the women cash for sex, Bambooyani and Askari arranged for their travel and lodging in several cities, including Phoenix, Las Vegas and Orlando, Florida, according to the plea.
Askari allegedly wrote a number of checks from his business bank account for as much as $6,000 after each of the trips. Bambooyani deposited many of the checks into his personal bank account, according to the charges.
FBI agents on Nov. 17, 2022, confronted Askari and showed him photos of some of the women and asked about the payments. The indictment alleged Askari lied when he “denied having sex with any of the women introduced to him by Bambooyani.”
He also falsely stated the payments he made to Bambooyani were reimbursements related to their business partnership — which public records show included real estate deals in Arizona.
Askari’s case is set for trial next year, although prosecutors have said that they are continuing to negotiate a possible plea with him as well.
Bambooyani is well known in several Chicago business circles, having teamed up with Weiss on a string of valet companies that provided services to pricey Rush Street restaurants and once had millions of dollars in city contracts to park cars on Chicago Public Schools properties as well as other city-owned locations.
On his Instagram profile, Bambooyani repeatedly refers to himself as the “Wolf of Rush Street” with photos depicting a lifestyle of cigars, nightclubs and travel to Turkey, the U.S. Virgin Islands and other exotic locations. One photo still on his profile shows Bambooyani having dinner at Gibsons Italia in Chicago in 2017 with a beaming Weiss and Toni Berrios.
When Bambooyani’s case was charged last year, he was represented by the same attorney as Weiss, Ilia Usharovich, who later withdrew from Bambooyani’s case due to potential conflicts, records show.
Meanwhile, Bambooyani’s connections to Weiss have surfaced in numerous news reports over the years, including in the Tribune.
In 2019, shortly after the sweepstakes gaming investigation went public, the Tribune reported the Teamsters union pension fund had sued Weiss and Bambooyani in U.S. District Court over allegations they spent a decade “using sham companies to avoid paying debts associated with their Chicago-based valet parking enterprise.”
The two denied the allegations, and the suit was settled in 2021 for an undisclosed sum, according to court records.
In 2018, the Chicago Sun-Times reported another valet company run by Weiss and Bambooyani, Blk & Wht Valet LLC employed a convicted child-sexual predator to help Cubs fans park their cars on a school parking lot near Wrigley Field.
And in 2020, Chicago Public Schools filed a lawsuit in Cook County alleging Weiss and Bambooyani stopped paying CPS for the rights to park cars at schools near Wrigley Field, but collected more than $350,000 from Cubs fans who parked there anyway, court records show. The judge in that case granted summary judgment in favor of CPS and awarded the agency about $50,000 in damages, according to court records.
jmeisner@chicagotribune.com