Roberto Caldero to plead guilty, says ‘at no time … would I be wearing a wire’

Political operative Roberto Caldero insisted on publicly telling a federal judge Thursday "at no time in the past or in the future would I be wearing a wire" after his lawyer confirmed Caldero intends to plead guilty in a corruption case involving ex-Ald. Danny Solis (25th).

Caldero made the statement during a hearing after lawyer Anthony Masciopinto and U.S. District Judge Steven Seeger advised against it. Before Caldero spoke, Masciopinto told the judge Caldero is "very concerned about living his life and trying to make a livelihood."

Despite the warnings, Caldero told the judge "I think we’re headed in the direction to resolve" the criminal case. And he said, "I just want a clear statement that any negotiations with the government does not include me discussing any other individual other than myself, and that at no time in the past or in the future would I be wearing a wire."


That’s when Seeger cut him off. The judge scheduled a May 26 hearing during which Caldero is expected to plead guilty.

Caldero’s comments come more than three years after the Chicago Sun-Times revealed that Solis recorded conversations for the feds — news that forced Solis’ early exit from public life.

Prosecutors hit Caldero more than a year ago with an eight-count indictment. It said he leaned on Solis in 2016 to help an Ohio company win a $1 billion custodial services contract at the Chicago Public Schools and to get a street and park named in honor of members of the Cacciatore family.

Roberto Caldero

Court records tie Caldero’s case to the separate indictments filed against former Illinois House Speaker Michael J. Madigan, Ald. Edward M. Burke (14th) and others.

The indictment against Caldero alleged that he offered Solis as much as $20,000 in campaign contributions to help land the custodial contract, as well as $50,000 in campaign contributions for the street and park re-naming. It said that Caldero bribed a high-ranking CPS official, Pedro Soto, with job offers, champagne and admission to an annual museum benefit.

As part of the scheme, Soto allegedly joined an evaluation committee considering bids for the contract and then gave "non-public" and confidential information to Caldero in 2016 and 2017.

Soto also allegedly gave higher scores to GCA Educational Services Central States Inc., and lower scores to its competitors, to help Caldero. Meanwhile, the feds say Caldero recruited Solis and asked Solis to put pressure on then-Mayor Rahm Emanuel.

Soto pleaded guilty in September 2020 to lying to the FBI and agreed to cooperate with federal prosecutors. He has not been sentenced.

Solis also plays a prominent role in the indictments against Madigan and Burke. Burke’s lawyers say Solis struck a so-called deferred prosecution agreement with the feds in January 2019 that could help him avoid prison time despite an investigation into his own corrupt activities.

That deal recently drew the ire of Mayor Lori Lightfoot, who said she’s "deeply offended" by the idea that Solis could just walk away without consequences.

Caldero’s name also surfaced in January 2019 in a bombshell federal court affidavit first obtained by the Sun-Times. Among other things, it alleged Caldero supplied Solis with Viagra and arranged for his visits to massage parlors.