Washington (CNN) - The last time William Barr was attorney general, a federal prosecutor brought criminal charges in a politically sensitive case days before the 1992 presidential election, a move George H.W. Bush would end up blaming for his resounding defeat.
Decades later, that October surprise -- an indictment from the Iran-Contra scandal -- serves as a backdrop to the long-simmering battle of wills that led to the bungled ouster last weekend of Manhattan US Attorney Geoffrey Berman, whose office has long been known for flexing its independence.
The attorney general's late Friday night announcement that Berman was stepping down, which Berman quickly refuted in his own press release, and the embarrassing standoff that followed, has damaged Barr's credibility.
Barr and other top Justice officials had come to view Berman and the Southern District of New York prosecutors as routinely refusing to abide by rules by which every other US attorney plays, according to people briefed on the matter.
This is the office investigating Rudy Giuliani, President Donald Trump's friend and personal lawyer, and Berman limited his briefings with Barr, curbing efforts by the attorney general to keep close tabs on this and other potentially sensitive cases, say people familiar with interactions between the two.
Tensions that have built up over the past year fed Barr's distrust of Berman and SDNY, these people say.
Justice Department officials in Washington were angered last year at the way prosecutors in Berman's office provided updates in the Giuliani probe early in Barr's tenure. Some Justice officials thought that New York prosecutors initially underplayed how much focus investigators already had on Giuliani.
Barr issued a memorandum in recent months ordering prosecutors around the country to ensure close coordination with the Justice Department on investigations that could affect the presidential election and restricting the FBI from opening investigations into 2020 political candidates or donors without sign-off from Barr or other top Justice officials, CNN has reported.
The one office that could possibly challenge the attorney general's edict was the fiercely independent office led by Berman.
Barr, in an interview with NPR on Thursday, dismissed suspicions of political interference behind Berman's removal, saying it had to do with making room for Jay Clayton, the chairman of the Securities and Exchange Commission, who had inquired about the job.
"I certainly was aware that given the environment, anytime you make a personnel move, you know, conspiracy theories will suggest that there's something, there's some ulterior motive involved," he said.
Clayton told a House hearing Thursday that he asked the President about the job two weeks ago.
The attorney general's standing has already been dented by clumsy interventions in cases involving the President's friends, notably Roger Stone and Michael Flynn, as well as the attorney general's involvement in a violent police crackdown on peaceful protesters outside the White House to clear the way for a presidential photo op.
A meddlesome manager
Two career prosecutors appeared before a House hearing this week alleging that Barr was abusing his power and making decisions based on what pleased the president. Barr rejected the accusations in his NPR interview, saying he adhered to the law in handling cases, including Stone's.
Barr has long been known among Justice officials as a meddlesome manager who believes in firm central control of US attorneys, a sentiment he described in an oral history project for the University of Virginia's Miller Center looking back at his work under during the Bush administration. Even then, he believed that Manhattan prosecutors were a thorn in his side.
"I think that if you have a strong attorney general and the backing of the President, you can keep the US attorneys in line," he said in the 2001 interview. "I think it just takes a little more work. The hardest one is obviously Manhattan."
A spokesman for the Manhattan US Attorney's office declined to comment for this story.
The investigation into Giuliani is ongoing and it isn't clear whether it will result in charges against Giuliani. Giuliani has denied wrongdoing and prosecutors haven't accused him of any.
People familiar with the inquiry expressed caution as to whether there is evidence Giuliani committed a crime.
Prosecutors have told indicted associates of Giuliani that additional charges against them could be brought by the end of July, according to people familiar with the probe.
But people familiar with Berman's thinking say the fired prosecutor made clear any decisions on charges between now and November would be made based on the evidence, not any potential political considerations.
Barr, in his Miller Center oral history interview, recalled how Independent Counsel Lawrence Walsh indicted former Defense Secretary Casper Weinberger four days before the 1992 election. Bush, he said, "felt that that indictment had cost him the election. He was very infuriated by it."
For Barr, the events of 1992 dovetail with his strong views on the expansive constitutional powers of the presidency, which he has argued, for instance, means that Trump's firing of former FBI Director James Comey shouldn't be cause for him to be investigated for potential obstruction of the investigation that Comey was leading.
Some Justice officials say Barr's efforts to protect the presidential power have increasingly appeared politicized in the era of an unorthodox president who regularly takes to Twitter to comment on Justice Department matters, dispensing with the restraint presidents have traditionally shown to protect the department from politics.
"I don't know what attorney general can manage this thing with that constant barrage of commentary that seems to show no respect for how the rule of law works," said Paul McNulty, who worked with Barr in the 1990s and later became deputy attorney general.
For his part, Barr complained in February about the President's Twitter posts related to criminal cases, saying the comments "make it impossible for me to do my job."
'It looks pretty swampy'
Barr's miscalculation in the effort to remove Berman on Friday night has only fueled suspicions of political interference, even among people who have generally supported him against such accusations.
Shortly after Barr issued a statement saying that Berman was stepping down, Berman issued his own press release disputing the attorney general's announcement. Berman said he was staying to protect sensitive cases.
In a Saturday letter notifying Berman that the President was firing him, Barr disputed any suggestion that there was any risk to cases pending.
"This is obviously false," Barr wrote. "I fully expect that the office will continue to handle all cases in the normal course and pursuant to the Department's applicable standards, policies, and guidance."
Berman accepted the President's firing only after Barr appointed Berman's trusted deputy Audrey Strauss as acting US attorney, but the damage from the standoff was done.
"From the outside it looks pretty swampy," Sen. Mitt Romney, R-Utah, told reporters days later, adding, "I certainly hope that any investigations that were being pursued that would relate to the President or donors or friends would be continued to be pursued."
Democratic lawmakers called for investigations into Barr's conduct, and have secured a date for him to testify in July.
South Carolina Republican Sen. Lindsey Graham, chairman of the Judiciary Committee and one of Barr's closest allies, called the handling of Berman's removal "inartful."
Graham expressed confidence that Barr acted properly, but also said he wouldn't allow a nomination to replace Berman to proceed unless he got agreement from New York's two senators, which isn't likely.
Graham also made it clear that he hadn't been consulted on Berman's removal or plans to nominate Clayton. That's an indication, some Justice officials say, of how badly Barr had miscalculated the Berman ouster.
"It's just not like Bill to paint himself into a cul-de-sac," said one friend of Barr, who declined to be identified by name.
The fallout from the Berman blunder extended to another prosecutor, New Jersey US Attorney Craig Carpenito, who Barr initially announced would temporarily oversee the Manhattan office.
Carpenito, in a conference call Saturday morning, told prosecutors and staff in his New Jersey office that had Barr called him on Friday and told him Berman was stepping down, and asked him to take over SDNY until Trump's nominee was confirmed by the Senate, according to a person familiar with the call. Carpenito said that he didn't know Berman was not resigning voluntarily. Talking Points Memo first reported the Carpenito call with prosecutors.
Justice officials have complained for years that Berman and prosecutors at SDNY, didn't follow normal protocols and were prone to surprise them in taking certain actions.
This includes the pre-Barr era 2018 decision, with relatively short notice, to identify the President, not by name but as Individual 1, as a conspirator in some of the crimes of his former attorney, Michael Cohen. Trump has denied wrongdoing.
Jostling over sensitive cases
Berman proudly defended the office's relative autonomy during the tenure of Attorney General Jeff Sessions. But tensions exacerbated when Barr took over in early 2019.
Barr quizzed Berman and wanted more frequent updates on cases, which Berman viewed as micromanaging, according to people familiar with the matter. Barr was also viewed as trying to influence certain investigative decisions by using internal legal opinions to pressure prosecutors, one person said.
Soon after Barr took office, Berman's office gave the attorney general a briefing on an ongoing investigation into Ukrainian associates of Giuliani, the President's personal lawyer, according to people briefed on the matter.
The briefing wasn't explicit about prosecutors' interest in Giuliani, according to people briefed on the matter, giving the impression that investigators may have to gain access to Giuliani's communications as an incidental part of the probe.
One person familiar with the investigation said that at the time of the briefing the investigation was still at an early stage.
Months later, Justice officials learned the case was much more politically sensitive. In mid-October, SDNY charged Giuliani's two associates with campaign finance violations as they were boarding an international flight. The men had been working with Giuliani on his effort to dig up dirt on Joe Biden and his son Hunter's work in Ukraine. The two have pleaded not guilty.
The charges came soon after the public airing of a whistleblower's allegations that during a call with Ukraine's president Trump withheld aid and sought an investigation into Biden.
After the charges were announced, it became clear that prosecutors were seriously investigating Giuliani's actions, including his efforts to oust Marie Yovanovitch, then-US ambassador to Ukraine, and push for an investigation into Hunter Biden. The inquiry quickly expanded into Giuliani's business dealings.
In the wake of these events, Barr appointed the US attorney in Brooklyn, one of Barr's favorites, to oversee matters related to Ukraine. It was a move perceived by Berman and his prosecutors as an attempt to coordinate the efforts by Manhattan prosecutors.
Barr and Berman also clashed over a decision to indict Turkey's Halkbank, another politically sensitive matter. The long-running investigation was raised by Turkey's President Recep Tayyip Erdogan in meetings with Trump in 2018.
In his new book, former national security adviser John Bolton says Trump told Erdogan that he would "take care of things," saying that the Southern District of New York prosecutors on the case were "Obama people" and would be replaced by "his people."
This fall, Barr sought to resolve the sanctions case with a deferred prosecution agreement, but Berman backed the position of his prosecutors to indict the bank. In the end, the bank was indicted.
Surprising that he was outmaneuvered by Berman
For Barr, the recent tussles in New York recall his complaints during his first time in office. His then Manhattan US attorney Otto Obermeier, in an interview, recalls that he spoke to Barr and told him "as little as possible."
Barr, in his Miller Center oral history interview, recalled that Obermeier "basically ignored 50% of what I said, just did it his way."
Tim Flanigan, who worked under Barr during that period, recalls Barr's reaction when Manhattan prosecutors were fighting off directives.
"I've heard him say," Flanigan recalls, "SDNY needs to remember that, number one, they're part of the Justice Department and, number two, they're part of the United States."
In his two stints as attorney general, Barr has earned a reputation as smart and confident, strong-willed and sometimes dismissive of arguments he doesn't think are well-thought out.
That's particularly true of issues related to the constitutional powers of the presidency, a theme that he's made central in his defense of Trump.
"I've always been just amazed by his ability to think both strategically and tactically," said McNulty, now president of Grove City College. "You'd better be ready if you're going to debate him or challenge his thinking."
It's partly because of that reputation for thinking ahead that supporters of the attorney general found it surprising that he seemed to be outmaneuvered by Berman into an embarrassing public spat.
But some Justice Department officials view the Berman episode as a predictable result of Barr's tendency at times to be a bully, so confident in his views that he can be blind to the damage to his and the department's reputation from the perception that he's too close to the president.
Early in his tenure, Barr set the tone of how he would approach the job by adopting some of the president's combative rhetoric about the investigations into his campaign.
When Barr issued statements at the close of the Mueller investigation, he portrayed some of the special counsel's findings as more favorable to the president than the full report turned out to be. That prompted Mueller to complain in a written letter.
Months later, it also earned him a rebuke from a judge who questioned Barr's "lack of candor" after reading the entire Mueller report as part of a lawsuit over redactions in the version Barr had released.
"The Court cannot reconcile certain public representations made by Attorney General Barr with the findings in the Mueller Report," U.S. District Judge Reggie Walton, an appointee of Ronald Reagan, wrote in March.
Walton added that Barr's initial interpretation of the report "cause the Court to seriously question whether Attorney General Barr made a calculated attempt to influence public discourse about the Mueller Report in favor of President Trump despite certain findings in the redacted version of the Mueller Report to the contrary."
The comments came amid controversy over Barr's handling of another case: the sentencing of Stone, one of Trump's friends. Prosecutors, abiding by Justice Department policy, recommended a stiff sentence for Stone's conviction on obstruction of a congressional investigation and false statements.
The President issued a tirade of criticism at the department and by morning, the department disavowed the prosecutors' sentencing recommendation. Barr intervened and sought a lighter sentence, prompting some prosecutors to resign from the case in protest.
More recently, Barr intervened to order charges be dropped against Flynn, the first Trump national security adviser who had pleaded guilty to charges of lying to the FBI.
The case is one that has fueled Trump's anger at the Justice Department and the FBI. Prosecutors who handled the case refused to sign the court documents Barr ordered to argue for dropping the case.
The move also prompted Judge Emmet Sullivan to appoint a retired judge, John Gleeson, to examine the Justice Department's arguments and determine whether Flynn should be held in contempt for lying to the judge.
Gleeson, in court documents, said the unusual moves ordered by Barr hurt the department's reputation. The Justice Department, Gleeson wrote, "has treated the case like no other, and in doing so has undermined the public's confidence in the rule of law."