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BRIDGEPORT, Conn.—On a recent Wednesday morning, Judge Stefan Underhill and a collection of lawyers gathered in the federal courthouse in Connecticut’s most populous city. They were there for the sentencing of Konstantinos Diamantis , once the state’s powerful school-construction chief.

Only one person was missing: Diamantis.

The defendant, who was convicted last year on 21 counts of extortion, bribery, conspiracy and lying to the FBI, was nearly 5,000 miles away in northern Greece.

“This is the first time I’ve gone to a sentencing with an empty chair,” Norman Pattis , Diamantis’s befuddled lawyer, told reporters outside the courthouse.

His client fled to his ancestral homeland ahead of a mid-September sentencing date, a move that has become the talk of the state’s political class.

While on the lam, Diamantis has tossed aside the standard fugitive playbook. Instead of lying low, he spends his days calling into a Connecticut talk-radio show, gabbing with hometown political reporters and circulating an eight-page manifesto asserting his innocence—in hopes, he said, of winning a pardon from President Trump.

“The Department of Justice (DOJ) District of Connecticut was used by the Governor of Connecticut, Ned Lamont , to weaponize the DOJ and to engage in legal warfare against me,” Diamantis wrote, in language seemingly tuned to the ear of the president whose favor he is seeking.

Cathryn Vaulman , a spokesperson for Gov. Lamont, a Democrat, rebuffed Diamantis: “The jury that convicted him has already rejected the fiction he is spinning now. He should return to Connecticut.”

In Greece, his dual citizenship complicates efforts by authorities to extradite him. But by fleeing he has jeopardized his right to appeal. The state attorney general is trying to revoke his pension. The federal government could own his house.

“Of course, it goes back and forth in my head: Is it the right decision?” Diamantis, 70, said in a phone interview. He had, by then, been on the run about two weeks and was losing track of time, he said. He wasn’t trying to escape justice, he claimed, but seeking a chance to tell his story. “I’ve lost everything,” he said. “The only thing that’s left is my dignity, right?”

The saga offers a glimpse of a Connecticut far removed from the hedge-fund wealth and old-money hamlets for which the “Land of Steady Habits” is often known. It features cash payoffs at a Dunkin’ Donuts and secretive meetings at the Capital Grille bar in Hartford (and, on one occasion, in its men’s room).

“We’re not New Jersey. We’re not Mississippi,” noted Seth Warren , a local-politics expert at the University of Connecticut, referring to other states with at times unsavory reputations for corruption. Still, he said: “There’s a lot of different interests that want to get a hand in the pie.”

‘I talked to those guys’

The son of Greek immigrants who settled in Bristol, Conn., “Kosta,” as he is known, became a lawyer and was elected in 1992 as a Democrat to represent Bristol in the statehouse. As often happens in Connecticut, he parlayed that experience into a full-time state job.

By 2015 he had become a power broker after then-Gov. Dannel Malloy put him in charge of the state’s school-construction grant and review office, overseeing hundreds of millions of dollars in annual spending. He later became a senior budget official, too.

“He had a position of enormous power—but not wealth,” said Pattis, his lawyer. Those who have dealt with Diamantis describe an affable man with a toothy grin who can also be domineering.

Tammy Nuccio was struck by his arrogance when she tangled with him as head of the town council in Tolland, outside Hartford. In 2019, the town had discovered faulty concrete in Birch Grove Primary School, and needed to rebuild it fast. It couldn’t afford the roughly $45 million project without state support, according to Nuccio, now a Republican state representative.

“He walked in like he owned the place,” she said. “‘This is what you’re going to do. These are the people you’re going to hire. This is what you’re going to pay them.’”

Diamantis describes his style differently. “Yes, I may have come across as domineering to keep people focused,” he said. “It was the reason I was the director.”

One firm he urged Tolland to hire, Construction Advocacy Professionals, received more than $500,000 in Birch Grove contracts soon after hiring Diamantis’s daughter, and its work was “entirely superfluous,” prosecutors said.

The project’s masonry contractor was a firm called Acranom, whose vice president, John Duffy , was Diamantis’s former brother-in-law and called him “Uncle.”

Acranom snagged a Birch Grove contract, of more than $2.5 million, despite a general contractor’s complaints that its work on another school was so poor much of it had to be redone, according to prosecutors.

In one seemingly brazen text message that emerged at trial, “Uncle” Diamantis informed Duffy: “I always usually work at 5% of total just fyi.”

Duffy, in turn, appealed to Diamantis when he feared Tolland’s general contractor was switching from masonry to drywall. “Tell Tony that his 45 mil included at least 3.4 for masonry and that has to stay. They changing it all to f——-g sheetrock… wtf.”

“I talked to those guys at Tolland,” Diamantis replied. “They got the message.”

Duffy and Acranom’s president, Salvatore Monarca , pleaded guilty to conspiring to bribe Diamantis—as did Construction Advocacy Professionals’ owner, Antonietta Roy . Her lawyer said: “Antonietta deeply regrets ever meeting Mr. Diamantis.”

In addition to the payoffs and messy politics of school construction, the trial also laid bare the desperation of an overextended bureaucrat juggling five daughters and two ex-wives—all while straining to pay for a Greek wedding and private-school tuition.

“I’m drowning,” Diamantis texted Duffy at one point, saying he had only $318 in the bank and was about to miss a mortgage payment. When Monarca was slow to pay, he fumed: “It’s like he’s pissing on me and making me crawl.”

Diamantis took the stand and said his payments were consulting fees. Jurors took little more than a day to convict him.

“What I was thinking about was: How does an innocent person end up in jail? How did I lose this case? How is it that they’re going to put me in jail at the age of 70 years old for, I don’t know, six, seven, eight, nine, 10 years?” Diamantis said of his reaction to the verdict.

Federal authorities say Diamantis fled to Florida, jumped on a boat to the Bahamas, and then flew via London to Athens—likely using a Greek passport he was supposed to have surrendered.

Diamantis, cagey about details, called the government’s version “plausible,” but not entirely accurate. He insists he reached Greece without any passport—or his family’s knowledge.

Of his journey, he observed darkly: “It’s not something you want to do.”

In Greece, he is staying at a friend’s apartment, he said, challenging reports that he had been living it up at a hotel bar. When not lobbying reporters or working on his case, he reads the news and takes walks, he said.

“It’s a different prison here,” he said. “It’s an emotional prison.”

‘A very nice conversation’

Back in Bridgeport, the sentencing proceeded last week like a wedding without a bride. “I’ve never had to deal with this before,” said Judge Underhill, a 27-year veteran of the bench.

As recently as the day before, there were signs Diamantis might return. He had bought a plane ticket, according to prosecutors, and a federal official had arranged to meet with him at the Athens airport to smooth his departure.

But Diamantis balked.

“Apparently, they had a very nice conversation but Mr. Diamantis told him he wasn’t going,” Jonathan Francis , an assistant U.S. attorney, told the court.

“He believes that the president of the United States will come to his assistance,” Pattis also told the court.

That doesn’t look promising. A White House official said Wednesday that the team that reviews clemency requests there “is not tracking this request at this time or even heard of this individual.”

In any case, the sentencing went forward with an empty chair at the defense table. “The public has waited long enough,” Francis said.

Channeling his client from afar, Pattis read a statement in which Diamantis again professed “my absolute innocence.”

In his own remarks, the defense attorney, who once taught a classics course, recounted the story of Antigone, the Greek princess sentenced to death for defying King Creon’s order not to give her brother a respectable burial. By the time Creon reconsiders, she has killed herself.

“Hence the tragedy,” Pattis explained. “He believes he’s in the position Antigone was in.” He asked the judge for mercy for a man he had described in a presentencing memo as “70 and effectively impecunious.”

Judge Underhill said that Diamantis had lied on the stand and called the evidence of his guilt “overwhelming. Period.”

Yet the judge stopped short of the 10-plus years prosecutors said would be appropriate, handing down a seven-year sentence. “As bad as his crimes are,” Underhill said, “he does not deserve to be in prison for the rest of his life.”

From Greece, Diamantis didn’t sound too appreciative. Even seven days would be “a lifetime to a 70-year-old innocent man who has lost everything,” he wrote in a text. “The sentence is a life sentence.”

Meanwhile, back in Tolland, the Birch Grove school is open. “The school’s great,” said Nuccio. “It’s built. It’s a great little school.”

Write to Joshua Chaffin at joshua.chaffin@wsj.com