Political operative pleads not guilty to fraud
Man has ties to former Ald. Daniel Solis investigation
A longtime political operative at the center of the investigation into former Ald. Daniel Solis pleaded not guilty Friday in alleged schemes to influence a massive Chicago Public Schools janitorial contact and solicit campaign cash for Solis.
Roberto Caldero, 68, was charged last week in an eight-count indictment with wire fraud, federal program bribery and facilitating bribery, allegedly in a plan to exchange the contributions for the alderman’s help renaming a street and city park.
He pleaded not guilty during a telephonic arraignment before U.S. District Judge Steven Seeger. The most serious charges call for up to 20 years in prison if convicted.
Caldero was released on an unsecured $10,000 bond, meaning he does not have to post any money.
Prosecutors said they want him barred from speaking to any victims or witnesses in the case, which would include Solis, former CPS executive Pedro Soto, and the Cacciatore family of Western Springs, who’d hired Caldero as a consultant.
During discussion of the bond, Caldero told the judge that he had questions about contact restrictions.
“So, some of the people on that list may or may not be close associates, friends of mine,” Caldero said, before his attorney, Anthony Masciopinto told him he’d rather speak about it in private.
Seeger set a status hearing for April 14.
Raised in Chicago’s Humboldt Park neighborhood, Caldero was a longtime political operative for former U.S. Rep. Luis Gutierrez dating back to Gutierrez’s
first run for City Council in the 1980s.
His name surfaced in an FBI search warrant affidavit made public in 2019 alleging Caldero had provided erectile dysfunction drugs and sexual services at a North Side massage parlor for Solis while he was lobbying the alderman on a variety of issues. Caldero has not been charged as part of that investigation.
Reached by telephone after the indictment was filed last week, Caldero denied any wrongdoing.
“I never offered anything to a public official or a government official — never anything in exchange for anything,” he told the Tribune. “Danny Solis was a friend of mine for 40 years. If he asked me for something I would try to do it for him. I attended every fundraiser he ever held. I raised $100,000
to $200,000 for him. None of that was a bribe.”
The indictment accused Caldero of participating in the same contract fraud scheme that ensnared Soto, a former chief of staff to Chicago Public Schools CEO Janice Jackson.
Soto pleaded guilty last year to lying to the FBI about whether he passed secret bid information about a $1 billion custodial contract to an operative working for one of the bidders. The operative was not named in those charges, but the indictment returned last week makes clear it was Caldero.
According to the charges, Caldero offered Soto a promise of future employment, Champagne and discounted event space for a family gathering, and admission to a museum benefit in exchange for Soto’s help landing the contract for Company A, a Cleveland-based janitorial services contractor that the Tribune previously identified as GCA Services Group.
In October 2016, Caldero asked Solis to “advise and exert pressure” on thenMayor Rahm Emanuel to help grease the wheels for Company A, saying that if Solis did so, the company would contribute $10,000 to his campaign fund, the charges alleged.
Caldero allegedly kept up the campaign for months, soliciting and delivering at least $5,000 in campaign checks for Solis in exchange for his assistance. In July 2017, Caldero asked Solis to put further pressure on officials at CPS, saying Company A would pay him another $15,000 “if we get this thing done,” the charges alleged.
Soto, meanwhile, admitted in a plea agreement with prosecutors that he lied to the FBI about his contacts with Caldero, saying he’d never discussed privileged information about the janitorial contract bid process with him or what favors he might get in return, court records show.
The contract ended up being awarded to a different bidder. Soto is cooperating with prosecutors and has not yet been sentenced.
At the same time as that alleged scheme, Caldero was accused of soliciting Solis’ help on behalf of Individual B, a business owner from Western Springs who was offering up to $100,000 in campaign donations to have Chicago issue an honorary street name for his father and rename a park for his grandfather, according to the charges.
The indictment alleged
Caldero told Solis the family wanted to see some action in the City Council before donating money. In October 2016, under the direction of investigators, Solis introduced an ordinance granting the honorary street name, the indictment alleged. The family cut Solis a $5,000 check two months later, according to the charges.
While the indictment does not name the family, records show the ordinance introduced by Solis that month renamed the 500 block of South Wells Street “Honorary Victor J. Cacciatore Sr. Way.”
The search warrant affidavit later made public in the Solis investigation alleged Caldero had solicited campaign donations from the Cacciatore family, which, among other businesses, owns Elgin Sweeping Services, a major street-sweeping company.
At the time, Caldero was representing Elgin Sweeping in its efforts to obtain relief from a change in the city’s water billing practices that investigators indicated could have cost the company more than $1 million.
The Cacciatores have not been accused of wrongdoing.
Solis resigned from the City Council before his cooperation was revealed in the bombshell indictment against his former colleague, Ald. Edward Burke. Court filings show he has entered into a deferred prosecution agreement with the U.S. attorney’s office.
The indictment does not name the park involved, but Caldero said it was Oscar D’Angelo Park on South Franklin Street.
D’Angelo, known as the “Mayor of Little Italy,” was a longtime confidant to former Mayor Richard Daley who was disbarred during the Operation Greylord scandal for providing rental cars as gifts to judges, politicians and city officials.