That error aside, Manafort’s alleged lies to Mueller during the time he spent cooperating—which his lawyers don’t want to challenge with a hearing, they revealed in Tuesday’s court filings—have likely damaged his chances of getting a light sentence. (Manafort’s lawyers said in Tuesday’s court filings that he did not intentionally lie to prosecutors. “These occurrences happened during a period when Mr. Manafort was managing a U.S. presidential campaign,” they wrote. “It is not surprising at all that Mr. Manafort was unable to recall specific details prior to having his recollection refreshed.”)

Manafort may be banking on a presidential pardon, which Trump has not ruled out. But the missteps of his attorneys appear to have done Manafort more harm than good.

Mariotti pointed to the public attack on the government by Kevin Downing, Manafort’s lead lawyer and a tax-law specialist, following a hearing in November 2017. He described the charges against Manafort—which included money laundering, bank fraud, and tax evasion—as “ridiculous” to reporters outside the courthouse, adding that there was “no evidence the Trump campaign colluded with the Russian government.” His comments led to a scolding from the judge and a court-imposed gag order. “There is no good reason to attack the prosecutors from the very beginning,” Mariotti said. Downing did not respond to a request for comment. A spokesman for Manafort declined to comment.

The unorthodox lawyering did not end there: Instead of having Manafort plead guilty and cooperate with prosecutors in exchange, potentially, for a more lenient sentence, Manafort’s lawyers effectively forced Mueller’s charges into two separate courts, putting Manafort at risk of having to sit for two trials instead of one. Legal experts scratched their head at that decision; Politico described it as “akin to choosing to play Russian Roulette with two bullets in the gun instead of one.” It was only after being convicted in Virginia on eight counts of financial fraud that Manafort decided to sign a plea agreement and forego a separate, impending trial in Washington, D.C., related to his unregistered foreign lobbying.

More than two months after Manafort agreed to cooperate, however, it was revealed that his legal team had never pulled out of its joint defense agreement with Trump’s lawyers—and had been providing valuable insights about the Mueller inquiry to them. Legal experts called the arrangement “extremely unusual”—and potentially unethical depending on what was discussed between Manafort’s lawyers and Trump’s team.

Barbara McQuade, who served as the United States attorney for the Eastern District of Michigan until 2017, said the arrangement raised questions “as to whether Manafort has simply been feeding information to, or lying for, Trump. Either scenario could amount to obstruction of justice by the subjects and even their lawyers if their intent is to interfere with the investigation.” A veteran Washington lawyer, who declined to be named because he represents an individual involved in the Mueller probe, told me at the time that he had “never in my life” heard of a defendant staying in a joint defense agreement after signing a plea agreement with prosecutors. “He had to have known how dangerous this was,” he said.