Political operative tied to Ald. Daniel Solis probe pleads guilty to fraud

A longtime political operative at the center of the investigation into former Ald. Daniel Solis pleaded guilty Friday to variety of fraud schemes, including an attempt to influence a massive Chicago Public Schools janitorial contact and using the alderman’s clout to solicit campaign cash and get a park and street renamed for a donor’s relatives.

Roberto Caldero, 69, entered his plea to honest-services fraud involving bribery during a video conference hearing before U.S. District Judge Steven Seeger. Under preliminary sentencing guidelines, Caldero faces up to about five years in prison when he is sentenced on Dec. 15.

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.

None of those allegations were contained in Caldero’s plea agreement with prosecutors. However, there was new mention of an elected official, identified only as Public Official A, whom Caldero enlisted to pressure then-Mayor Rahm Emanuel to support the awarding of the CPS janitorial contract to a company Caldero represented.

According to the plea, Caldero told an associate in December 2016 to “keep Public Official A happy” until he met with the mayor, and enlisted another person, Individual D, to supply marijuana for Public Official A’s birthday in 2016.

Gutierrez’ in 2017 made a surprise announcement that he was not running for reelection for the Congressional seat he’d held since 1993.

Caldero also admitted in his 23-page plea agreement to participating in a contract fraud scheme that also ensnared Pedro Soto, a chief of staff to former public schools CEO Janice Jackson.

Soto pleaded guilty in 2020 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 paperwork later filed by prosecutors made it clear it was Caldero.

According to Caldero’s plea, he 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 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, an indictment filed against Soto last year 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 the school contract scheme, Caldero was also 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 Caldero’s plea agreement.

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 Tribune has previously identified the park as 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.

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. He since has entered into a deferred prosecution agreement with the U.S. attorney’s office, which has agreed to drop bribery charges against him in three years if he continues to cooperate.

jmeisner@chicagotribune.com