George Conway Says Donald Trump Will Go to Prison Over Obstruction

Donald Trump faces going to jail for obstruction in connection to the classified documents investigation against him, according to lawyer George Conway.

Conway is a frequent Trump critic who separated from former White House counselor Kellyanne Conway. He said that the former president, who denies all wrongdoing, is facing a "strong" case of obstruction over the top-secret documents retrieved by the FBI at his Mar-a-Lago resort in Florida. Conway was discussing an update to Special Counsel Jack Smith's inquiry.

On Monday, The New York Times wrote that prosecutors have subpoenaed The Trump Organization for information about the former president's business dealings since he entered the White House in January 2017. It is unclear why the subpoenas were issued, but is yet another sign that Smith is expanding his federal probe into Trump.

trump George conway
Former President Donald Trump speaks at a campaign rally on April 27, 2023 in Manchester, New Hampshire. Lawyer George Conway said the former president faces going to jail for obstruction in connection to the classified... Spencer Platt/Getty Images

Conway said on MSNBC's All in With Chris Hayes that Trump did not need a "financial incentive" to keep the classified materials at his Florida home. His "insane narcissism and his belief that he controls everything" meant he believed he was allowed to do so.

"The only thing that could really make this worse is if [Trump] had a FedEx slip showing that he sent them to the Saudis or the Kremlin or whatnot," Conway said. "And maybe he did that almost. Anything is possible with this guy.

"But the thing that's interesting about this is it's not necessary to put this man in jail. It doesn't matter whether he gave these documents to a foreign power—it makes it much, much worse because it would be an independent violation of the Espionage Act—[but] it almost doesn't matter whether he showed off [North Korea leader] Kim Jong Un's letter to visitors, because the obstruction charges are so strong," Conway added.

"I mean, Ty Cobb, the White House counsel who handled in the Trump administration, handled the Mueller investigation went on national television the other day and said, 'Trump's going to go to jail for this.' And he should and he will, because the obstruction case is just so strong."

Trump is accused of willfully obstructing the federal attempt to retrieve the classified documents, which were removed from the White House in January 2021.

Trump received a government subpoena to hand over all the materials to the National Archives and Records Administration in May 2022. Trump is alleged to have ignored the requests. The Washington Post reported in April 2023 that the former president looked through some of the boxes of government documents out of an apparent desire to keep some of the materials.

In June 2022, the FBI visited Mar-a-Lago to recover the classified materials. During the visit, Trump's legal team is alleged to have "explicitly prohibited" federal agents from looking inside a storage room at the resort.

Trump lawyer Evan Corcoran then drafted a statement, signed by fellow Trump attorney Christina Bobb. He told federal investigators that all the classified materials being kept at Mar-a-Lago were returned in June.

The FBI then raided Trump's Mar-a-Lago home in August 2022 and seized more than 100 classified and top-secret documents, including some found in the storage room.

Last March, Corcoran testified to a grand jury for a second time as part of the classified materials investigation to answer questions under oath without being able to cite attorney-client privilege.

Washington D.C. District Court Judge Beryl Howell ruled that prosecutors can force Corcoran to void the normally protected privilege under what is known as the crime-fraud exception. This means that the protected attorney-client privilege cannot be invoked if a lawyer and their client are allegedly attempting to cover up or engage in a crime.

Elsewhere during his MSNBC appearance, Conway said Trump being accused of getting his lawyers involved in his alleged offending will not be taken lightly by a judge.

"Judges are lawyers. They were practicing lawyers, they respect the attorney-client privilege, and to pierce that privilege is something they don't like to do," Conway said. "And the fact that Judge Howell was willing to do it shows that the evidence is incredibly strong."

Newsweek has contacted Trump's legal team for comment via email.

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Newsweek is committed to challenging conventional wisdom and finding connections in the search for common ground.

About the writer


Ewan Palmer is a Newsweek News Reporter based in London, U.K. His focus is reporting on US politics, domestic policy ... Read more

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