Exposed: The devastating failure that pushed lawyer to risk prison for Trump

Failure at a prestigious law firm pushed an elite lawyer into Donald Trump's orbit — and now he faces prison as a fall guy for the administration's policies, a report claimed Tuesday.

And Politico found Drew Ensign's professional path has left former classmates and colleagues staggered.

Ensign found himself at the center of a legal storm in March that would define his reputation as a Department of Justice lawyer. During an unusual court hearing, Ensign claimed ignorance about ongoing deportation plans by the Trump administration. "I do not have additional details I can provide at this time," he told U.S. District Court Judge James E. Boasberg.

The judge, unconvinced, ordered the government to halt the deportations, telling Ensign, "This is something that you need to make sure is complied with immediately."

But compliance was not forthcoming. Two planes filled with Venezuelan immigrants had already departed Texas, landing in El Salvador hours after the judge's order. Boasberg would later describe how the government "obscured" the flight details, with Ensign "surprisingly represent[ing] that it still had no flight details to share."

Ensign's subsequent legal arguments became increasingly confrontational. He characterized the judge's inquiries as a "judicial fishing expedition" and "intrusions into the prerogatives of the Executive Branch." A whistleblower report would later allege that Ensign "willfully misled the court" about the deportation plans.

Boasberg has ruled there is probable cause to find the government in contempt for ignoring his order. If that happens, Ensign is likely to take the fall.

"If Ensign is ultimately found to be in contempt — a slim but real possibility — he could be fined, lose his law license or even face prison time," Politico wrote.

His actions stunned former colleagues. "It's shocking to see somebody of his caliber and somebody who has been trained at a firm like Latham [& Watkins] out there making these arguments," said an anonymous former colleague. Another suggested that "nobody who Drew has worked with" would think he was "making really good decisions personally."

Ensign's trajectory was anything but typical. A Duke and NYU Law graduate who spent a decade at the prestigious law firm Latham & Watkins, he had never been a vocal political activist. His political donations were modest and mainstream, primarily supporting traditional Republican candidates like John McCain.

But he wanted to be a partner at Latham and, after being passed over, he was reportedly furious.

“Drew worked unbelievably hard,” a former colleague told Politico. “I think that was just a real disappointment for him.”

“Over time, there was a lot of bitterness on his part about how things had worked out at Latham,” the colleague said. Another said, “He was pretty salty about not being made partner. Definitely resented his circumstances at Latham after a while.”

He moved to a different firm, and eventually to Trump's Department of Justice.

The consequences of the move could be severe. As Nancy Gertner, a retired federal judge, noted, "When the Trump administration is over and he seeks jobs, [his actions] will be something that people will raise: 'you misled, you deceived, you withheld information.'"

Ensign could face significant professional sanctions. As Rachel Barkow, an NYU Law professor, explained, a court would need to find that he "personally violated a court order willfully" to impose contempt. However, she added a crucial caveat: even if found in contempt, Trump could potentially pardon him.

At his law school reunion, Ensign faced the judgment of his peers. A classmate reported that his colleagues were "uniformly disgusted at how he's been willing to deploy his legal skills on behalf a lawless administration."