As U.S. District Judge Steven Seeger sentenced longtime Chicago political operative Roberto Caldero to nearly five years in prison for wire fraud Friday, he placed the man in the city’s infamous history of political corruption.

Caldero — who pleaded guilty in September as he faced eight charges for attempting to influence a $1 billion Chicago Public Schools janitorial contract and using former Ald. Daniel Solis’ clout to solicit campaign cash and get a park and street renamed for donor’s relatives — had made his mark, Seeger said.

“You added another star on Chicago’s walk of shame on the sidewalk of corruption,” the judge told the 70-year-old during a five-hour-long hearing.

The judge slammed the Humboldt Park native, whose close work with former U.S. Rep. Luis Gutiérrez dates back to the 1980s, before delivering the 57-month sentence, a judgment in the middle of suggested sentencing guidelines for the case.

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

But before his fate was dealt, Caldero repeatedly broke from his lawyer’s advice to air his own perspective before the court.

Early in the sentencing hearing, the political operative argued that he felt the process was in some ways unfair. It’s like he’s getting targeted for a bounced check, he said.

“And other people were robbing the bank,” Caldero added.

The company he was working for would have been fine with only one $30 million to $50 million portion of the $1 billion CPS contract he tried to win, he insisted.

Caldero’s name surfaced in an FBI search warrant affidavit made public in 2019 alleging he 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.

But it was ultimately Solis’ stunning turn as a government mole that ultimately led to his February 2021 federal indictment for other alleged offenses, as well as separate recent charges against two of Chicago’s most powerful politicians: 14th Ward Ald. Edward Burke and ex-House Speaker Michael Madigan.

As Caldero directed, arranged and managed bribe money that was funneled into Solis’ campaign in exchange for helping secure the CPS janitorial contract, the political operative stood to gain a lucrative five-year contract with the company, court records show.

A matching five-year sentence would have been “poetic justice,” Seeger said, but the judge stopped three months short of the pairing.

“I think you deserve five years. Candidly, probably more,” he said.

Seeger offered an onslaught of metaphors as he dug into the defendant. Caldero was “a weapon of mass corruption” with far-reaching “corrupt tentacles” who drove the “corruption train,” he said.

If the crimes were a movie, Caldero would’ve been “director, if not executive producer,” he said. The political operative seemed comfortable “directing traffic on the corruption highway” and dangling “carrots of corruption” in front of public officials, Seeger added.

“It sure makes me wonder if this is your first ride in the corruption rodeo, because you seem awfully comfortable,” the judge said.

Seeger said he was shocked when Caldero decided to make an unnecessary statement in an earlier hearing to say for the record that he would not wear a wire or talk about other individuals in cooperation with the federal government.

The move reminded him of the classic Martin Scorsese mob film “Goodfellas,” Seeger said.

“You seemed to be telegraphing to the world that you are not a snitch. You were telling your friends that you didn’t rat anyone out,” the judge said.

As Seeger reflected aloud on the aggravating and mitigating factors before delivering a sentence, Calderon continued to part from the advice from his attorney, Sami Azhari, to remain quiet.

At one point, Caldero took to the mic and began to tell a story. When he dropped Madigan’s name, Azhari pressed hard to stop his client. Seeger reminded Caldero that he was not required to speak and unsubtly hinted to him that he’d be best off following his lawyer’s advice.

After pausing to talk with his lawyer, the defendant told Seeger he would not make a statement after all, only to interrupt discussion between the attorney and judge in an attempt to speak again moments later.

“He’s advised not to speak for the duration of this. If I’m not clear enough on this already,” Azhari said for the record, hitting his hand on the table.

Eventually, Caldero conceded to his attorney’s advice.

“Let’s finish this,” he told the judge.

Seeger said the many letters commending Caldero’s character from friends and family affected his sentence. Caldero’s daughter recalled his work fighting gang violence and his loving care as she testified before the court.

“He got caught in the slime of Democratic machine politics,” she said.

Caldero wiped his eyes as his daughter spoke through tears — tears matched then and during the final sentencing by many of the around 20 people watching from the back of the wood-paneled courtroom. He looked away from her as she described his incessant smiles and habit of saying “I love you.” Afterward, he closely hugged her.

[ ‘What did you say they would give me?’: 1st undercover recordings by Ald. Daniel Solis made public in corruption case ]

But the man’s long record of working in politics made the case particularly discouraging, Seeger said, who argued that Caldero should have known better.

The judge cited video released to the Tribune earlier this week and shown in court. The video, recorded by a Solis-worn hidden camera, captured Caldero discussing an apparent bribe for helping convince other alderman and then-Mayor Rahm Emaneul to steer the CPS janitorial contract to the company that hired Caldero as a consultant.

Watch the video:

The videos never showed Caldero discussing how the expensive contract could best serve Chicago schoolchildren or what might be best for the community, the judge said.

“You were so cavalier. You were so natural,” Seeger said. “The conduct in question here was not a momentary lapse in judgment.”

He asked Caldero how many politicians he knows who have been indicted — “six to eight,” per the defendant — before declaring that a message needs to be sent that public corruption doesn’t pay in a city that has long been synonymous with cheating politicians.

Corruption undermines the public’s faith in democracy and leads to bad governmental decisions, Seeger told the court.

The judge ordered Caldero to surrender on June 7, after one of his daughters graduates from college. He is to face probation for two years after serving at the federal prison closest to Chicago, though he won’t face fines, in part because of a staggering $700,000 in unpaid federal taxes, Seeger determined.

Earlier in the hearing, the judge had fixated on the name of the park Caldero had worked to rename for a client with apparent bribes. The park was named for Oscar D’Angelo, the judge said.

Seeger asked the attorneys if they knew who D’Angelo, who died in at 84 in 2016, was. They did not, they said.

The infamous Chicago power broker, known as the “mayor of Little Italy,” had been disbarred in Illinois during the Operation Greylord scandal for providing rental cars as gifts to judges, politicians and city officials, he told them.

Caldero offering bribes to rename a park named for a politico who had similarly doled out questionable generosities had a “poetic quality,” Seeger said.

“You can’t make that up,” he said. “Only in Chicago.”

jsheridan@chicagotribune.com