Wayne Simmons was a professional football player, a drug trafficker, a nightclub doorman, a Fox News guest analyst and an intelligence adviser in Afghanistan.

What Simmons, 62, was not, according to all available evidence, was a CIA agent. In federal court in Virginia on Friday, just before he was sentenced to 33 months in prison, he apologized for lying about his security clearance, his criminal history and his finances.

“There is not a day that goes by that I am not haunted by these mistakes,” Simmons said. “I stand before you a shameful and broken man.”

But Simmons, who wore a blue suit and an American flag lapel pin, did not back down from his claims that he spent 27 years as an agency operative doing work so dangerous and secretive that it went entirely unrecorded. He said Friday that he lied his way into military contractor work to make use of a “special skill set” he implied was acquired undercover.

Judge T.S. Ellis III was unconvinced.

“I read spy novels,” the judge said before issuing his sentence. “Every spy novel has black-ops, off-the-books operations. Maybe these things exist.”

He said that, like the many people Simmons fooled, he was initially impressed by the defendant’s charisma and “fascinated” to see what proof Simmons would offer — only to get none. Simmons’s supposed CIA career, he concluded, was “not just implausible but beyond incredible.”

Over the years, Simmons’s claims were convincing enough to get him a regular spot as an unpaid commentator on Fox News; a post on a 2013 civilian panel investigating the attacks in Benghazi, Libya; and two jobs with defense contractors working in Afghanistan.

[He claimed to be ex-CIA. Prosecutors say it was a lie.]

Authorities first began investigating Simmons in the fall of 2013 when a woman he had a romantic relationship with came to the FBI saying he had taken her money in a real estate scam. The probe ended up going much deeper.

Authorities excavated Simmons’s life and career, starting with his claim that he was recruited to the CIA out of the Navy in 1973.

In fact, according to prosecutors, Simmons was discharged from the Navy for medical reasons just a couple of weeks after he enlisted. And former CIA officials told the government that they did not recruit agents out of basic training.

Simmons went on to briefly work on a pipeline in Alaska and then played football for several years with the semi-pro Baltimore Eagles and the National Football League’s New Orleans Saints.

Again, his career was cut short by medical problems, according to the records provided by the government.

Each of the missions Simmons claims to have then undertaken on behalf of the CIA was, according to a long court filing from prosecutors, merely the scheming of a petty criminal.

“Wayne Simmons is a fraud,” Dana J. Boente, U.S. attorney for the Eastern District of Virginia, said in a statement. “Simmons has no military or intelligence background, or any skills relevant to the positions he attained through his frauds.”

“Operation Iranian Trust,” which Simmons described in his own court filings as “an undercover investigation of a political extortion, cocaine, heroin, and arms trafficking organization” in the D.C. area in the 1970s and ’80s, was just a job as a doorman at a nightclub partly owned by an Iranian expatriate and a side business dealing cocaine, prosecutors said.

The government contends that “Operation New England,” supposedly a similar investigation in Boston in the 1970s, was a brief job trafficking marijuana for a major drug dealer. And that “Operation Kazakhstan” was not an intelligence-gathering mission involving the Central Asian country in the 1990s but a business venture undercut by Simmons’s excessive drinking.

Defense officials told investigators that a 1996 operation to “recover a very special alloy or object, most likely a Picosatellite,” simply never happened. Finally, Simmons’s Grasonville, Md., CIA safe house was, in the government's assessment, just a dilapidated vacation home.

Four former senior CIA officials interviewed by prosecutors said the dramatic undercover operations Simmons described were imaginary.

David Cohen, a former director of the clandestine service, called the descriptions so “far-fetched” and “inconceivable” that they were nothing more than a “Hollywood script.”

But in 2001, a chance meeting with a public-relations professional helped Simmons parlay his supposed CIA career into the commentator’s spot on Fox News, according to court filings. A Fox spokeswoman noted that he was not paid and that his last appearance was in March 2015.

After starting at Fox, Simmons became part of a group of military veterans cultivated by the Defense Department under Donald H. Rumsfeld. He traveled to Guantanamo Bay with the group. Former Pentagon officials, including Rumsfeld, told prosecutors that there was no vetting done to be in the program, because it required no security clearance.

Rumsfeld later wrote a letter supporting Simmons’s effort to have his wife buried at Arlington National Cemetery, according to prosecutors.

Through his Fox News contacts, according to prosecutors, Simmons in 2008 got a job with defense contractor BAE Systems to help the military in Afghanistan deal with the local population.

But Simmons was cut before he deployed because he got such low marks in training, according to court records. Col. Steve Rotkoff, deputy director of the program, told prosecutors that the defendant was “act[ing] like a fictional CIA character instead of an actual CIA operative.”

A year later, Simmons failed to get a job with a contractor doing international security for the State Department; an internal State Department memo called his CIA career “a comical fantasy.”

But in 2010, he was hired by a defense subcontractor to advise on counterinsurgency tactics in Afghanistan, a position Gen. Stanley A. McChrystal told prosecutors was “hugely important” to the war effort. Simmons deployed to Kabul, but his interim security clearance was revoked after two weeks, and he was sent home.

It was then that Simmons persuaded a woman with whom he had a relationship to give him $125,000 for a fake real estate investment.

When his promises did not materialize, she went to authorities, telling the government she had trusted Simmons in part because of his Fox News appearances and purported CIA career.

Simmons will have to pay $175,000 in restitution to the government and to the woman, who came to court Friday but declined to speak publicly.

Simmons pleaded guilty in April to major fraud against the United States, wire fraud and being a felon in possession of a firearm. His prior record includes firearms, assault and gambling offenses, prosecutors said.

Had the case gone to trial, defense attorney William B. Cummings said, the defense could have called to the stand a former government prosecutor who claims that the CIA has lost or lied about records in the past.

Simmons also has repeatedly blamed his predicament on political machinations.

After his arrest last year, according to court documents, Simmons emailed Keith Urbahn, former chief of staff to Rumsfeld, and said that the charges were “all lies and innuendo” because he had “succeeded in becoming the number one enemy of Pres Obama and Hilary Clinton.”

Assistant U.S. Attorney Paul Nathanson predicted in court that Simmons would find a way to “roll with” the sentence while continuing to lie about his past.

“He’s hedging himself so he can maintain this aura of mystery,” the prosecutor said.

Matt Zapotosky contributed to this report.