Politically connected businessman James Weiss heads to trial amid swirling investigations, intrigue

Chicago businessman James Weiss may not exactly be a household name, but he’s spent his life running in the city’s powerful political circles.

The grandson of a former deputy city treasurer and friend of Mayor Richard Daley, Weiss married into the family of longtime Cook County Democratic boss Joseph Berrios, ran a political action committee with ties to then-House Speaker Michael Madigan, hooked up with Iranian American businessman who calls himself the “Wolf of Rush Street” on a series of lucrative valet parking companies, and later, through connections with a fired Chicago cop and the help of a state legislator, got into the shady, unregulated world of sweepstakes gaming machines.

Now, some of those connections are about to be put under a microscope in a federal courtroom, where Weiss went on trial Monday on federal bribery charges alleging he agreed to pay off a state senator in exchange for support on legislation that would benefit the sweepstakes gaming industry.

Jury selection in the case, which is expected to last about a week, is still ongoing. Opening statements could come as soon as Tuesday.

It’s a trial filled with political intrigue, both in the lineup of current and former elected officials expected to the take the stand as well as the backdrop of ongoing federal investigations swirling around Weiss’ associates, including the Cook County assessor’s office — which Berrios once helmed — as well as Madigan, other members of the Illinois General Assembly, and Bambooyani, who was quietly indicted last month on charges he arranged for high-end prostitution services for his friends.

Weiss, 44, who is married to Berrios’ daughter, former state Rep. Toni Berrios, is charged in a superseding indictment filed in October 2020 with bribery, wire fraud, mail fraud and lying to the FBI. He has pleaded not guilty.

The indictment alleges Weiss paid bribes to then-state Rep. Luis Arroyo beginning in November 2018 in exchange for Arroyo’s promotion of legislation beneficial to Weiss’ company, Collage LLC, which specialized in the sweepstakes machines.

The bribes were paid via off-the-books lobbying payments to Arroyo’s consulting firm, Spartacus 3 LLC, according to the charges.

Both Weiss and Arroyo also conspired in 2019 to pay then-state Sen. Terry Link, a Vernon Hills Democrat, $2,500 a month in kickbacks in exchange for Link’s support on the proposed sweepstakes game legislation, the indictment alleged.

Link, who resigned from office before pleading guilty to unrelated tax evasion charges, secretly recorded meetings with Arroyo and Weiss that are expected to be played for the jury at Weiss’ trial.

In addition to Link, who has never publicly acknowledged his turn as a government mole, the key witnesses lined up to testify against Weiss include former state Sen. Tony Munoz, a Chicago Democrat, current state Rep. Robert Rita, D-Blue Island, and Patrick O’Connor, a longtime Chicago alderman, court records show.

One name not on that list is Arroyo, who pleaded guilty to his role in the alleged scheme but did not agree to cooperate with prosecutors. U.S. District Judge Steven Seeger sentenced Arroyo to nearly five years in prison last year, calling him a “corruption superspreader.”

By taking his case to trial, Weiss is rolling the dice on what could wind up being a far longer sentence than Arroyo’s. Adding to the intrigue is the status of Weiss’ own attorney, who made a last-ditch effort to delay the trial that culminated in a bizarre pretrial conference last week and rebukes from both the trial judge and the 7th U.S. Circuit Court of Appeals.

A transcript of the hearing showed that the attorney, Ilia Usharovich, was scolded repeatedly by the judge for inappropriate behavior before being ordered to remain silent unless called upon. Usharovich tried to drop out of the case and began to walk out of the courtroom but was ordered back by the judge, according to the transcript. He later claimed he grew physically ill from the stress and was forced to vomit into a cup because Seeger prevented him from going to the bathroom.

“Here, judge, look in the cup,” Usharovich said, according to the transcript. “There is spit in here.”

“I’m not going to look into the cup to see if you have vomited into the cup,” Seeger replied. “Maybe you spat into the cup. I don’t know.”

After Usharovich insisted it was indeed vomit, Seeger said, “You’re clearly behaving in a way that is unhinged and troubling to me and disrespectful, and that’s going to end.”

Later, the judge issued an order that marked one of the starkest public smackdowns of an attorney in recent memory, saying Usharovich’s “disruptive, disrespectful and contemptuous” conduct “was on full display from the outset of the hearing, and devolved from there.”

“Frankly, the display that this court witnessed tests this court’s ability to put the conduct into words and fully capture what transpired,” Seeger wrote in the order. “For whatever reason, Usharovich was unable to control himself, and was unable to follow repeated admonishments from this court about how to comport himself.”

Under the judge’s orders, Usharovich filed a written acknowledgment that he’d read the assessment of his behavior and was aware that sanctions, including being kicked off the trial, would come down if he failed to behave professionally.

There were no dust-ups between Usharovich and the judge Monday, as the judge spent hours questioning a pool of 32 prospective jurors about their backgrounds, their ability to be fair and their thoughts about political corruption.

Among the panel was a retired man from Lake Forest who said he’s all-too familiar with the litany of local elected officials who’ve run afoul of the law.

“Reading the paper, you know, Martin Scorsese should come here and he should do a film called ‘The Chicago Way,’ ” he said. “It’s something we’d all be familiar with.”

Another prospective juror, a woman from the city’s Northwest Side who works in IT, said she may be biased by “a lifetime of hearing about the Chicago machine and the corruption in Chicago politics.”

“I don’t know that I can be impartial,” she said. “That’s a lifetime to unlearn.”

Both of those jurors were later excused for cause.

The case against Weiss centers on the largely uncharted world of sweepstakes machines, sometimes called “gray machines,” which allow customers to put in money, receive a coupon to redeem for merchandise online and then play electronic games like slot machines.

Since the machines can be played for free, they are not considered gambling devices. Critics, however, contend the unregulated devices, which operate in cities, including Chicago, that have banned video gambling, are designed to skirt the law.

State business records show Weiss was connected to the former cop, John Adreani, through a complex web of corporations, many of which listed the same address in a south suburban strip mall as their headquarters.

Adreani and his company, V.S.S. Inc. — identified in the charges only as Company B — inked a deal in 2018 to pay Arroyo $2,500 a month to lobby City Hall on proposed legislation allowing sweepstakes machines to operate in the city, lobbying records filed with the city Board of Ethics show.

Adreani was fired from the Police Department in 2015 for associating with a major drug trafficker after he was captured on a wiretap discussing gambling and drinking excursions and real estate ventures with him, according to Chicago Police Board records.

Meanwhile, Arroyo was captured on an undercover FBI recording in August 2019 telling Link there was good money in it for him if he’d help shepherd pro-sweepstakes legislation in Springfield, according to the charges against Arroyo.

“If I’m doin’ OK, you’re gonna do OK,” Arroyo allegedly told Link. “We’ll talk to each other to make sure that you’re rewarded for what you do. ... Same way I’m getting paid, I’m getting paid 2,500 dollars a month.”

Weiss was not named in the original complaint filed against Arroyo, but his alleged involvement in the scheme was first reported by the Tribune several days later. At the time, Weiss declined to comment on his role in the investigation when a reporter knocked on his door in River Grove, saying, “I have no idea what’s going on.”

When asked for his cellphone number, Weiss said, “They took it.” He then shut the door.

Court records since made public show that Weiss indeed had his cellphone seized by two FBI agents who confronted him near his home the day that Arroyo was charged. Prosecutors say that Weiss willingly got into the agents’ car and answered questions for nearly an hour, denying knowledge of the alleged bribery scheme.

In addition to marrying into the politically powerful Berrios family, Weiss is also a grandson of former Deputy City Treasurer Edward Murray, a longtime Bridgeport precinct captain. Murray also served as a financial officer for the Chicago Public Schools.

One of Weiss’ chief business partners Iman Bambooyani, a flashy entrepreneur who calls himself “The Wolf of Rush Street.” Together they own a string of valet companies that had millions of dollars in city contracts to park cars on CPS properties as well as other city-owned locations, records show.

Bambooyani, 42, was quietly charged on May 8 with one count of transporting individuals over state lines for sex, which carries a potential sentence of five years in prison. Usharovich also represents Bambooyani in that case.

Also charged was 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.

Thought it’s unclear if Bambooyani’s charges were connected to the Wiess probe, their business connections 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 lawsuit claimed Weiss and his partner emptied one company, Capital Parking LLC, of assets to avoid paying nearly $100,000 owed to the union for employee benefits.

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. They have denied the allegations, and the suit was still pending as of Friday, records show.

NOTE: A previous version of this story incorrectly identified former state Sen. Tony Munoz as a former state representative.

jmeisner@chicagotribune.com