When a stone-faced Michael Flynn entered courtroom 24 in the US district court in Washington DC on Tuesday, it looked like a cozy deal arranged with prosecutors – no jail time in exchange for a guilty plea and full cooperation – was already sealed.

But no one was counting on Judge Emmet Sullivan.

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While Mueller’s prosecutors had argued Flynn’s decades of military service warranted a lenient sentence for the three-star general even after he had admitted lying to the FBI, it was Sullivan who, gesturing to the American flag beside him, accused Flynn of selling his country out. Minutes later, he ponderously asked the government’s lawyers whether they had ever considered charging Flynn with treason. (No, they later answered.)

“Arguably,” Sullivan said, describing how Flynn had secretly been working for the Turkish government before he joined the White House, “that undermines everything this flag over here stands for.”

It was an unexpected moment that seemed to capture – perhaps for the first time – the depth of the betrayals at the heart of special counsel Robert Mueller’s criminal investigation. So far, the cast of characters that have been ensnared by the inquiry, from Trump adviser George Papadopoulos to Trump campaign chair Paul Manafort, have seemed relatively minor players on the world stage. But not Flynn, who had been entrusted with keeping the country’s most classified secrets and protecting its security.

“I am going to be frank with you, this crime is very serious,” the judge said. “I can’t hide my disgust, my disdain, at this criminal offence.”

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Even the scene of the crime – the West Wing of the White House – seemed to gnaw at Sullivan, who repeated it several times, all the while emphasizing how unusual it was that the government and Flynn were asking him to bless a plea agreement even though Flynn had not completed his cooperation with the government.

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Sullivan also quickly clamped down on any suggestion that Flynn’s admitted crime – lying to federal investigators – had occurred in part because the retired general had been lulled into thinking his interview with the FBI was simply a chat, and not part of a criminal investigation.

Never in his decades on the bench, Sullivan said, had he accepted a guilty plea from a defendant who was not really guilty. “I don’t intend to start today,” Sullivan said, and then had Flynn sworn in. “Any false answers will get you in more trouble,” he added.

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Months after Flynn led chants of “lock her up” at the Republican national convention, in reference to Hillary Clinton, it was the three-star general who was then forced – without hesitation or excuses – to admit to his crimes.

Even then, Sullivan told Flynn he ought to consider a delay in his sentencing because there were no guarantees, the judge said, that he would not be incarcerated. After a brief recess, Flynn, looking subdued and a little stunned, returned with his answer: he would take the delay and thereby possibly avoid a harsher sentence.

Then came more bad news for Flynn on what Sullivan had in mind. He was clearly keen to convince Flynn that jail time was still on the table.

“I didn’t say ‘wink, wink, nod, nod’,” Sullivan declared. “I’m not promising anything.”