(CNN) They once were Donald Trump 's strutting, sharp-suited alpha male political and legal fixers, living high and playing the game hard, seemingly immune from the consequences of their willingness to walk on the dark side.

One is already in jail, another is headed there and Stone narrowly escaped with his liberty Thursday but was gagged by a judge he had threatened on Instagram

All three men have been indicted or convicted or have pleaded guilty to crimes and alleged offenses that in most cases are not directly linked to their work for the President.

But had they not eagerly dived into Trump's shark tank and had he not run for President they would not have drawn the attention of special counsel Robert Mueller and possibly other prosecutors in cases that led to their downfall.

The White House line, whenever one of the President's men goes down, is that none of it has anything to do with Trump. Technically, that is often true: So far none of the trio has been charged with a conspiracy to collude with Russia, for instance.

What is clear is that these are men who Trump has been happy to have by his side. While their partnerships were working and before prosecutors swooped, he never seemed troubled by their dubious reputations and bare-knuckle tactics. In fact, it may have recommended them to him.

Stone, a protege of Trump mentor and mob law yer Roy Cohn , has moved in the President's world for decades. He is his longest political adviser, after a self-styled career as a dirty trickster fashioned after his hero Richard Nixon.

Cohen, who is expected to lift the lid on some of the President's life and business secrets in what could be a sensational Capitol Hill hearing next week , made himself indispensable as a man who cleaned up Trump's messes.

And Manafort traded in the life of a jet-setting international political consultant who rubbed shoulders with oligarchs to turn Trump, the 2016 GOP primary victor, into a nominee who could make a run at the presidency itself, as his campaign chairman.

If their story has a common moral, it is this: Sooner or later, even hard-charging political and legal bruisers who seem to fly unrestrained by the normal rules can eventually fall foul of the law and see lives of notoriety crash to ruin.

Only time, Mueller, various other legal proceedings and a flurry of congressional investigations will tell whether Trump himself will learn the same hard truth or was smart enough to avoid the fate of his tainted operatives.

'Attack, attack, attack'

"Attack, attack, attack -- never defend," he said. "Admit nothing, deny everything, launch counterattack."

That was his approach a few weeks ago in his first court appearance in Florida , when he was defiant and reveling in the attention -- flashing Nixon's "V for victory" sign with his hands above his head on the courtroom steps.

But there was no attack, attack, attack on Thursday. That Roger Stone was nowhere to be seen in a Washington courtroom. He was abject and apologetic after he was hauled in to explain his Instagram post.

His bravado drained out of him on the day a life of political chicanery finally claimed its price.

"I don't offer any rationalization or excuse or justification. This is just a stupid lack of judgment," he told the furious judge, pleading his case by saying he was having trouble putting food on the table and paying rent owing to legal fees.

Stone has been walking the line, and crossing over it, for decades. In effect, he was being cross-examined by Judge Amy Berman Jackson for being Roger Stone. And now, thanks to the full gag order, which will prevent him talking about the case in the media, that persona must go silent on the subject that interests him most -- his political tricks.

"He has played this character for his entire career, and today I think he went up against the wall," said David Urban, who masterminded Trump's victory in Pennsylvania in the 2016 campaign and is now a CNN commentator.

"He has always pushed the line, and I think he went over that line today and he got smacked down pretty hard by the judge," Urban said on CNN's "The Lead."

Jackson told Stone that his apology rang hollow and she wasn't impressed with his explanations.

"This is not baseball. There will not be a third chance," she said.

The depth of his plight might have begun dawning on Stone as the gag order was formally imposed.

"He just put his head in his hands, he leaned back and it looked like his eyes were closed, letting the reality of this sink in," said CNN reporter Kara Scannell, who was in the courtroom.

Cohen vows he will not be Trump's 'villain'

Cohen attached himself to Trump more than a decade ago, glorying in the role of the legal strongman who took care of business.

"They say I'm Mr. Trump's pit bull, t hat I'm his right-hand man," Cohen once said. He was not beyond threatening reporters in the vernacular of a mobster.

When his famous client became a presidential candidate, Cohen turned himself into a political surrogate for the man he always referred to as "Mr. Trump."

"He took care of what had to be taken of. I don't know what had to be taken care of. But all I know was Michael was taking care of it," Trump campaign aide Sam Nunberg told CNN's Gloria Borger last year.

Once, Cohen said he'd "take a bullet" for Trump.

No more. The former fixer now feels that his association with Trump has led him to personal destruction. In December, a federal judge sentenced him to three years in prison for crimes that included arranging payments during the 2016 election to two women who claimed affairs with Trump.

"The man doesn't tell the truth ... And it is sad that I should take responsibility for his dirty deeds," Cohen told ABC's George Stephanopoulos in December, saying he had lied for Trump for 10 years "out of loyalty to him."

"I will not be the villain of his story," Cohen said.

After several false starts, Cohen is due to testify to the House Oversight Committee next Wednesday in public, in what could turn into one of the most compelling congressional circuses in recent memory. While Cohen is likely to paint a grim picture of Trump, Republicans will seek to impugn his credibility, given that he is already a proven liar.

Cohen caused a stir on Thursday by sho wing up on Capitol Hill and spending several hours in the Senate Intelligence Committee's secure rooms ahead of his closed-doors testimony to that panel, also scheduled for next week. Senators are likely to quiz him on many issues -- including his efforts to broker a Trump Tower project in Moscow, even during the presidential campaign.

A broken man

Another Trump associate who tumbled to earth in the most humiliating fashion was Manafort.

Before he was snared by Mueller, Manafort was an uber-lobbyist and the epitome of Washington's swamp culture, exporting the dark arts he learned as a GOP operative to several unsavory political characters abroad.

He worked for pro-Russian politicians in Ukraine, in just one of the contacts that have drawn the interest of Mueller.

The work was lucrative. His riches bought an ostentatious wardrobe that included ostrich and python skin jackets. He shopped at House of Bijan, reputedly the most expensive men's store in the world, according to court documents.

Manafort also built a bloated real estate portfolio, with one home boasting an outdoor kitchen financed from offshore accounts. His Hamptons hideaway included a $10,000 karaoke system and a giant flower bed in the shape of an M.

But his spending sprees also led him to take a $10 million loan from a Russian oligarch close to President Vladimir Putin, a connection that has raised suspicions that he might have been compromised by Moscow.

Now Manafort may be facing the rest of his life in jail.

He will be sentenced for his conviction of financial fraud on March 8, a federal judge in Virginia said Thursday. He will be sentenced in Washington, where he pleaded guilty to conspiracy and broke a plea deal with Mueller, on March 13.

Even before long years behind bars, Manafort is a painfully diminished figure.

In his most recent court appearance last month, he had to ask the judge for permission to wear a suit instead of his dark green prison duds.

His sunken appearance and now almost completely gray hair shocked observers -- after he limped into court using a cane -- in contrast with the cocky self-assurance he once showed while lording over the Trump campaign.

As he left the courtroom, Manafort blew a kiss to his wife, Kathleen.