Guilty Illinois Sweepstakes Machine Company Owner Seeks Leniency

Written By Hill Kerby on October 6, 2023
Photo of a judge and a gavel for a story on a gambling machine maker who was found guilty of bribery in Illinois

A man convicted of fraud, bribery and lying to FBI agents when they found out he had been paying off state legislators to pass laws that favored his business is seeking leniency.

That is the short list of crimes Illinois businessman James T. Weiss committed in an attempt to pass Illinois gambling legislation to legalize sweepstakes machines. His company, Collage LLC, manufactures the machines.

Now, Weiss is pleading for mercy from US District Judge Steven Seeger, who is set to sentence the convicted man for his crimes. Weiss seeks a 27-month sentence.

Feds flipped senator to catch Weiss

Weiss’ actions date back to 2018 before Illinois Gov. J.B. Pritzker signed the gambling expansion bill that legalized Illinois sports betting and made way for six new Illinois casinos. Weiss wanted the bill to include specific language legalizing sweepstakes machines. He paid then-state Rep. Luis Arroyo $2,500 monthly to help make that happen.

Sweepstakes legislation, however, never made it into the bill. The duo then enlisted then-senator and chief sponsor of the gambling bill Terry Link.

The FBI, though, had discovered that Link had committed his own crimes in falsifying tax returns. He cooperated with the agency, hoping to reduce his sentence by obtaining proof of Weiss and Arroyo’s dealings.

Weiss was charged with his crimes in October 2020, a year after including Link in his bribery efforts. He was convicted in June and now awaits sentencing from Seeger. Prosecutors’ recommended sentence was due on Oct. 4.

Sweepstakes machines are similar to the online casinos in Illinois that follow the sweepstakes model. (Any real-money online casino operating in Illinois is not regulated.) Players are not required to pay any money to play the games. Some of their winnings, however, can be redeemed for certain prizes, once they’ve accumulated enough. It’s a legal workaround that social casinos like LuckyLand Slots and SweepSlots Casino use to operate legally in most of the US.

Judge unlikely to provide leniency

In addition to catching Weiss, the operation revealed Arroyo had participated in a $62,500 bribery scheme. He faced up to a 20-year prison sentence and a $250,000 fine. His lawyers asked for probation.

The judge overseeing Arroyo’s case was also Seeger. Arroyo’s lawyers offered up two reasons for probation. Arroyo had retired, and a more significant sentence would not affect the city’s already corrupt political climate.

They said sending Arroyo to prison would be “no more effective than draining Lake Michigan with a spoon.”

Seeger said he needed a bigger spoon and sentenced Arroyo to nearly five years in prison.

Weiss, too, faces a maximum 20-year prison sentence. He undoubtedly will receive more than the 27 months he is requesting.

It’s not The Windy City for the weather

I remember visiting Chicago in 2016, arriving at a friend’s house around 6 p.m. and quickly jumping into a taxi to see a Cubs game at Wrigley Field.

“You know, they don’t call it The Windy City because of the weather,” said my cab driver once he found out it was my first time in town. “It’s because of the politicians.”

Weiss has political pull throughout the city, donating over $80,000 to sweepstakes machine legalization efforts and running the Alliance of Illinois Taxpayers, which has raised hundreds of thousands of dollars. Its primary donator was a group of personal injury law firms associated with House Speaker Michael Madigan.

Madigan is one of four political insiders accused of participating in a bribery scheme that lasted nearly a decade. The four were convicted in May on corruption charges. Madigan’s trial is set for April 2024. Weiss is close friends with Madigan’s son, Andrew.

Weiss and his mother also run two charities supported by members of the Chicago politics realm. He also held contracts with city-owned parking lots near Chicago sports venues and downtown.

He has other political connections, including to former deputy treasurer Edward J. Murray, his wife and former state Rep. Toni Berrios, along with her father-in-law, Joseph Berrios, a former Cook County Democratic Party chairman and ex-county assessor.

This case and Link’s tax crimes are only two recent examples of politicians committing crimes in The Windy City. Weiss was the sixth person convicted this year by a federal jury, all from federal investigations into Chicago’s public corruption.

A case for regulation

Alderman Gilbert Villegas (36th) was a major recipient of Weiss’ contributions. He introduced an ordinance in 2018 to legalize, regulate and tax sweepstakes machines in Chicago. He defended his position in 2019.

“Either you outlaw them or regulate them. They’re around.”

Indeed, history dictates that those words are true. Black markets thrive where regulated markets do not exist.

The same goes for “legal gray areas,” such as in Chicago, where business owners operate unregulated machines and do not pay taxes like licensed gambling operators. A judge has never ruled that sweepstakes gambling is illegal, allowing the market to run without oversight.

City and state officials must remove the gray area, deeming these machines legal or illegal. If the former, the machines could generate tax money like any other form of gambling. If the latter, authorities could crack down on black market operators.

A clear solution exists.

Photo by Shutterstock
Hill Kerby Avatar
Written by
Hill Kerby

Hill Kerby is a proponent of safe, legal betting, and is grateful to be able to contribute to growing the industry. He has a background in poker, sports, and psychology, all of which he incorporates into his writing.

View all posts by Hill Kerby
Privacy Policy