Attorney General William Barr testifies before the Senate Judiciary Committee on May 1, 2019. Credit: Diego M. Radzinschi / ALM

Tim Shea was running out of time.

It was May, and Shea was nearing the end of his 120-day appointment as the acting U.S. attorney in Washington. By then, the former aide to U.S. Attorney General William Barr had some baggage, his tenure marked by uproar over the Justice Department leadership's intervention in the sentencing of Roger Stone and the abandonment of the case against former Trump national security adviser Michael Flynn. In both instances, Barr had made moves to shield allies of the president.

Shea needed a court appointment to extend his tenure, and that month he was scheduled to appear via video-conference before the federal trial judges in Washington. Ahead of the May 19 meeting, it became clear he lacked crucial support.

In a phone call, U.S. District Judge Beryl Howell informed Shea that she could not support an appointment making him the U.S. attorney, according to three people familiar with the conversation. Howell, the chief judge of the Washington federal trial court, had expressed support for Shea before his office moved in early May to drop the Flynn case, a Justice Department official said.

On May 18, Barr named Shea to a new interim post—acting head of the Drug Enforcement Administration—and the Justice Department announced the president's intent to nominate Justin Herdman, the U.S. attorney in northern Ohio, to serve as the top federal prosecutor in Washington.

Another Barr adviser, Michael Sherwin, stepped in to lead the Washington prosecutor's office in the meantime.

In an office traditionally led by a lawyer with Washington ties, the reshuffling replaced the Boston-rooted Shea with Sherwin, a veteran federal prosecutor in Miami, and put the U.S. attorney in Cleveland in line to take over. And it deepened a sense of disarray and upheaval that, combined with the coronavirus outbreak, has drained morale within the largest U.S. Attorney's Office in the country.

"Having worked in that office for the better part of my career, I can only imagine it is unsettling for most [career prosecutors], and that is because in any U.S. Attorney's Office, particularly in D.C.'s office, which serves as the local and federal prosecutor, you need stability. That just hasn't occurred in that office over the past several months," said Channing Phillips, who served from 2015 to 2017 as the acting U.S. attorney in Washington.

"Any administration has the right to replace any U.S. attorney they want. This administration, though, in two instances, obviously, has chosen to select interim U.S. attorneys who really have no ties to the office, which is OK. But they have no ties to the community either," he added.

A Justice Department spokeswoman declined to comment.

Sherwin told The National Law Journal that since taking over the Washington office in May he has stressed to career prosecutors he views his role as supporting them and having their backs "100%."

"I think we're going through unprecedented times. Few U.S. attorneys who've ever held this office have had to confront a public health crisis coupled with social unrest and a litany of politically charged cases," Sherwin said. "It's a combination of multiple factors that make working at the U.S. Attorney's Office at this time very challenging. That being said, I want the office to know and the community to know that I am, one, a career prosecutor."

Sherwin continued: "I understand the challenges of being an AUSA, and despite significant turnover from Jessie Liu to Tim Shea to myself, the office should know that I have their back 100%. And, under my leadership, this office will be fully transparent and not only meet, but exceed, our legal and ethical obligations on behalf of this community and the United States."

Turnover amid turmoil

The turnover at the top of the U.S. Attorney's Office began in January, when Jessie Liu stepped down as she awaited confirmation to serve as an undersecretary at the U.S. Treasury Department overseeing sanctions enforcement. Liu had been the Senate-confirmed leader of the office.

Jessie Liu, U.S. attorney for the District of Columbia, in Washington, D.C., April 12, 2019. Photo: Diego M. Radzinschi/ALM

A former Morrison & Foerster white-collar partner, Liu had expected to remain the top prosecutor in Washington as her nomination to the Treasury role was pending. But at the end of 2019, she was pressed to leave the prosecutor's office sooner as part of what Barr's team billed as a push to have steady leadership through the duration of 2020, according to officials familiar with Liu's departure. After leaving the Washington prosecutor's office, Liu took a role at the Treasury Department, only to resign after the Trump administration pulled her nomination to the undersecretary post.

The handoffs of power in the office have played out as prosecutors have dealt with the dramatic aftermath of the Justice Department abandoning its case against Flynn, who twice pleaded guilty to lying to the FBI, along with litigation over the Stone case.

Trump's commutation of Stone's 40-month prison term inflamed the perception that Barr had acted just weeks earlier to help a friend of the president's. Before Trump's clemency announcement, Barr had reiterated in a televised interview that he viewed Stone's prosecution as "righteous" and saw the 40-month sentence as fair, saying the judge had "effectively" agreed with him that the prison term originally recommended by career prosecutors was overly harsh.

In the Flynn case, U.S. District Judge Emmet Sullivan refused to immediately grant the Justice Department's motion to dismiss and instead appointed a former federal judge in Brooklyn, John Gleeson, to review the unusual bid to drop the prosecution. Flynn has contested Sullivan's review, and the Justice Department backed his challenge in the U.S. Court of Appeals for the D.C. Circuit.

A divided three-judge panel of the D.C. Circuit ordered Sullivan to dismiss the case, ruling that he overstepped his power when he set up a plan to review the Justice Department's decision to drop the prosecution. Sullivan, who has not yet granted the Justice Department's request to dismiss the case, has asked the full D.C. Circuit to take up the dispute.

Jonathan Kravis. Credit: Diego M. Radzinschi / ALM

Thousands of former prosecutors have questioned the Barr Justice Department's moves to benefit Stone and Flynn. One prosecutor on the Stone case, Jonathan Kravis, quit the Justice Department in response to Barr's decision to withdraw a sentencing memo that career prosecutors had filed and replace it with a new one that asserted Stone should face a lower potential prison sentence.

"In both cases, the department undercut the work of career employees to protect an ally of the president, an abdication of the commitment to equal justice under the law," Kravis, now a partner at Munger, Tolles & Olson, said in an op-ed in May. "Prosecutors must make decisions based on facts and law, not on the defendant's political connections."

Another prosecutor on the Stone case, Aaron Zelinsky, told a House panel in June that the trial team came under "heavy pressure from the highest levels of the Department of Justice" to give Trump's friend a "break." Zelinsky, a career federal prosecutor in Maryland, withdrew as a special assistant U.S. attorney detailed to the Washington office following Barr's intervention in the Stone case.

Filling out the front office

Shea joined Barr's front office at Main Justice in April 2019 from the law firm Morgan, Lewis & Bockius, where his clients included Google, Eli Lilly, Purdue Pharma and Capital One Financial. Shea had spent five years at the firm before his arrival at the Justice Department. The attorney general named him acting U.S. attorney in late January.

Earlier in his career, Shea held a top role in the Massachusetts state attorney general's office and served as chief counsel and staff director of the Senate Permanent Subcommittee on Investigations, under the leadership of U.S. Sen. Susan Collins, a Maine Republican. He had previously served as a federal prosecutor in eastern Virginia and, under the George H.W. Bush administration, as a top Justice Department adviser during Barr's first stint as attorney general.

On the evening of March 27, in an email, Shea announced the arrival of Sherwin—his eventual successor—to the staff of the U.S. Attorney's Office in Washington.

"Please join me in welcoming Michael R. Sherwin as the new Principal Assistant United States Attorney," Shea wrote. He continued with a 400-word summary of Sherwin's career, giving an overview of his 12 years as a federal prosecutor in Miami and an earlier stint as a naval intelligence officer. Shea did not make reference to Sherwin's work investigating the 2019 shooting at the Pensacola Naval Air Station, which had impressed Barr and Justice Department leadership, and his role in the prosecution of a Chinese businesswoman who was found guilty of trespassing at Mar-a-Lago, a Trump-owned club in South Florida.

In the same email, Shea expressed his "deep gratitude" for the top deputy in Liu's front office, Alessio Evangelista, who stayed on for weeks as principal assistant U.S. attorney and oversaw the office's response to the coronavirus outbreak.

Evangelista had spent years as a line prosecutor in Washington, experience that lent him legitimacy when Liu recruited him back to the office in late 2017 from the Justice Department's criminal division. He had been interviewed for the acting U.S. attorney role, according to people familiar with the process, but Barr ultimately appointed Shea.

The maneuvering at the top of the U.S. Attorney's Office received renewed attention recently after Barr and Trump ousted the top federal prosecutor in Manhattan.

Barr tried to orchestrate the removal of Geoffrey Berman as the U.S. attorney in Manhattan and replace him with Jay Clayton, chairman of the U.S. Securities and Exchange Commission. In a New York hotel room, over sandwiches that went uneaten, Berman drew comparisons to the Washington prosecutor's office as Barr pressed him to step down and take a new job within the administration.

"At one point I compared his request for my resignation to what happened with the U.S. Attorney's Office in the District of Columbia where the U.S. attorney resigned and was replaced with someone from outside that office instead of the first assistant," Berman said earlier this month, in prepared testimony to the House Judiciary Committee. "By referring to that resignation I intended to signal the Attorney General that I was not going to resign so that he could disregard normal procedure and appoint someone from outside the Southern District as acting head instead of our deputy U.S. attorney."

Barr had picked New Jersey's U.S. attorney, Craig Carpenito, a former Alston & Bird partner, to serve as the would-be acting head of the Manhattan office on Berman's departure. Berman agreed to step down last month, he said, only after being assured that his top deputy, Audrey Strauss, would step in as acting U.S. attorney. Strauss now leads the Manhattan office.

Confusion over criminal division

On his arrival at the U.S. Attorney's Office, Sherwin focused on investigations arising out of the coronavirus outbreak, including an ongoing insider-trading probe of U.S. Sen. Richard Burr, R-North Carolina, over stock sales made just before the pandemic sent markets plummeting. Burr, represented by a team from Latham & Watkins, has denied any wrongdoing.

In April, Sherwin recruited a former colleague from Miami, Maria Medetis, to take a top position in the criminal division of the Washington office. Her move to the nation's capital was met with puzzlement, and some shock, thanks in part to communication from the U.S. attorney in Miami, Ariana Fajardo Orshan.

In an email to the South Florida prosecutor's office, Fajardo said Sherwin had been asked by Barr to become the top assistant U.S. attorney in Washington, adding that he must have impressed the attorney general, according to people familiar with the email. Fajardo went on to say that Sherwin, as a leader of the office, had recruited Medetis to become chief of the Washington office's criminal division.

There was one problem: Medetis was joining the division as deputy chief.

As it circulated in Washington, Fajardo's note raised eyebrows, in part because the longtime prosecutor in the office, John Crabb, was leading the criminal division as acting chief at the time.

In the initial confusion, career prosecutors viewed the announcement as a slight against Crabb. For them, the rollout—along with the arrival of an outside prosecutor from Miami to oversee a division still reeling from the controversy around Stone's sentencing—contributed to a growing sense of unease, according to people familiar with the episode.

Sherwin approached at least two other lawyers in the Miami office to gauge their interest in coming to Washington, according to a person familiar with his recruitment efforts. He also contacted multiple trial attorneys in the fraud section of the main Justice Department's criminal division.

A representative for the U.S. Attorney's Office in Miami declined to comment on Fajardo's internal announcement.

Shea did recruiting of his own. Early in his tenure, he approached a former Georgetown Law Center classmate, Evan Corcoran, about becoming a top aide in his front office. Corcoran, who had served in the 1990s as a federal prosecutor in Washington before going on to become a partner at the law firm Wiley Rein, was in the process of joining the office as a counselor to Shea. But the move fizzled with Shea's departure in May.

Restructuring in the criminal division

As Shea's four-month appointment wound down, Sherwin oversaw discovery issues connected to the Flynn case as Jeff Jensen, the U.S. attorney in St. Louis, conducted an outside review of the prosecution. Sherwin advocated for the release of materials that surfaced in that review, which were later cited in the Justice Department's full retreat from the prosecution.

"I would suspect morale in that office is just through the floor with the way Shea was brought in and how he then started overruling prosecutors in the Stone and Flynn cases. All of the stuff that's happened is so contrary to the kind of historical principles and ways that office operates, the way any good prosecutor's office should operate," said Randall Eliason, a professor at George Washington University Law School who led the public corruption and government fraud section of the U.S. Attorney's Office from 1999 to 2001.

"That flip-flopping based on political considerations, which has been at least questioned by several judges—it's disheartening to see from the outside. And I suspect it's extremely disheartening and disruptive inside to the front-line prosecutors," he added.

Meanwhile, the criminal division of the Washington prosecutor's office underwent a restructuring. In the most significant change, the office's new leadership broke up the section that had handled Stone's prosecution, dividing the fraud and public corruption unit into two parts.

The reorganization created a stand-alone fraud unit, with a focus on economic crimes, including coronavirus-related fraud. The broken-off section focusing on public corruption and civil rights prosecutors mirrors a unit in the criminal division of the U.S. Attorney's Office in Miami.

Within the office, some prosecutors have questioned the timing of the reorganization, wondering why it is proceeding amid a global pandemic that has forced staff to work from home, according to people familiar with the reaction.

Sherwin's appointment as acting U.S. attorney in Washington took effect May 19, making him the third leader of the office in six months. In an officewide conference call shortly after taking over, Sherwin underscored his background as a career prosecutor and announced that Crabb, the acting chief of the criminal division, had been promoted to hold the position in a permanent capacity.

Sherwin has kept other career prosecutors in the Washington office atop the newly reshuffled sections. A veteran prosecutor, J.P. Cooney, who oversaw the fraud and public corruption section and is spearheading the Burr investigation, has been named chief of the unit focused more squarely on public corruption. Jonathan Hooks, the chief of the cyber crime unit, is set to become chief of the stand-alone fraud section.

Cleveland prosecutor gets the nod

Sherwin's initial weeks as acting U.S. attorney thrust him into the Justice Department's lawsuit over Trump national security adviser John Bolton's memoir, along with the response to widespread protests in the aftermath of the killing of George Floyd in police custody.

In the Bolton case, a judge rejected the Justice Department's 11th-hour bid to prevent the release of Bolton's book, noting that the damning memoir had already been widely distributed, but signaled that the government might prevail in its push to seize the onetime Trump adviser's proceeds from the book.

Acting U.S. Attorney Michael Sherwin appearing on Tucker Carlson's Fox show this month. Screen grab from Fox.

Days before the Fourth of July, Sherwin appeared on Fox News to tout the administration's efforts to protect monuments amid mass protests.

"People can't unilaterally decide what is right and what is wrong. If those people do make that decision on their own and take the law into their own hands, the law will come after them, and the United States will use federal resources to charge you if you're inciting violence or destroying these monuments," Sherwin told Fox News anchor Tucker Carlson.

On the May conference call where he introduced himself, Sherwin did not mention Herdman, the Cleveland prosecutor and former Jones Day partner who had been announced as the administration's choice to lead the Washington office in a permanent capacity, according to two people familiar with the virtual meeting.

The omission fanned questions within the office and larger Washington legal community about the Trump administration's level of commitment to Herdman's confirmation, according to people familiar with the reactions of career prosecutors.

"Justin has taken an increasing role in the leadership of the Department and this nomination is a reflection on his sharp intellect, sound judgment, and dedication to the mission of the Department of Justice," Barr said in a statement in May. "Justin has proven himself to be a fair prosecutor, capable litigator, and excellent manager, and I look forward to his confirmation by the Senate for this important position."

Two months since announcing its intent to make Herdman the U.S. attorney in Washington, the Trump administration has yet to formally send the nomination to the U.S. Senate. The White House declined to comment, and the U.S. Attorney's Office in Cleveland did not respond to requests for comment.

A Justice Department representative said the department's understanding is that the White House is moving forward with the nomination.