Political operative Roberto Caldero sentenced to nearly 5 years for bribery scheme

Caldero, 70, a consultant and activist, was charged with trying to bribe indicted Ald. Danny Solis and a CPS official.

SHARE Political operative Roberto Caldero sentenced to nearly 5 years for bribery scheme
Dirksen Federal Courthouse.

Dirksen Federal Courthouse.

Sun-Times file

Longtime political operative Roberto Caldero on Friday was sentenced to just under 5 years in federal prison for bribing city officials.

In a sentencing hearing that dragged on more than five hours— with Caldero repeatedly interrupting the judge despite the best efforts of his beleaguered attorney — U.S. District Judge Steven Seeger praised Caldero’s long history in Chicago politics, and as an activist working for immigrant rights and against gang violence.

But more recent history, captured on hidden camera by FBI informant and former City Council member Danny Solis, showed Caldero glibly laying out a plan to steer a Chicago Public Schools janitorial services contract worth as much as $1 billion to a company that had hired him, as well as explaining how a connected family planned to reward Solis with campaign donations for his help in renaming a city park for a relative.

In handing down a 57-month sentence, Seeger noted how on the video, Caldero, then 64, had bragged to Solis that he could fund five years of his retirement with his cut of a kickback for a janitorial contract.

“You were bribing a public official to set you up for five years, and I thought to myself, wouldn’t it be poetic if the bribe for a five-year retirement plan turned into five years in the federal penitentiary,” Seeger said, adding that he opted for a slightly lower sentence based on pleas for leniency from Caldero’s family.

Now 70, Caldero pleaded guilty last year to funneling cash to Solis and former CPS executive Pablo Soto in the CPS contracting scheme, as well as for Solis’ help in getting the city to rename that park, as well as a street. Seeger noted the park had been named for Oscar D’Angelo, an attorney disbarred for bribing judges in the 1980s Greylord scandal.

“The case involves bribing a public official to rename a park, and the park is named for a public official involved in corruption,” Seeger said, shaking his head. “You can’t make that up. Only in Chicago.”

Early in the hearing, Seeger asked a probation officer why Caldero had told a probation official that his prosecution was “unfair.”

Caldero then asked to speak.

“I think at one point the federal prosecutors, the FBI were coming after me for the equivalent of a bounced check while other people were robbing the vault,” Caldero told the judge. “I did not understand at first that I was breaking the law ... whether I intended to or not, it’s a violation of the law and I have to take responsibility for a violation of the law.”

The statement would come back to haunt Caldero hours later during Seeger’s colloquy.

“You’ve been in political circles for so long — you know the rules,” Seeger said.

“You didn’t know you were in violation of the law? Really, Mr. Caldero?... Let me make this clear: You can’t bribe people. And I can tell you, Mr. Caldero: You knew it.”

In his remarks, Seeger, who last year handed a 57-month sentence to former state Sen. Luis Arroyo in an unrelated bribery scheme, pondered whether the many convictions of public figures in Chicago had done much to stem political corruption in the city.

“It makes me wonder if the sentencings in this building for public corruption are long enough. It makes me wonder whether ... judges need to send a louder message that the public will not tolerate public corruption. I don’t know why the message is not getting out.”

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