Hillary Clinton, the first lady at the time, stops to talk to reporters in January 1996 before testifying in front of a grand jury in the Whitewater investigation. (Susan Biddle/The Washington Post)

Over the course of 16 hours, prosecutors and FBI agents agonized over whether to charge Hillary Clinton with a crime. In the end, after weighing every ounce of evidence, examining piles of documents and gaming out whether a jury would ever convict her, the group made its wrenching decision: no charges.

Nearly 20 years before FBI Director James B. Comey declared that “no reasonable prosecutor” would bring a criminal case against Clinton over her use of a private email server while secretary of state, Clinton narrowly escaped a similar legal peril amid the Whitewater investigation that engulfed much of her husband’s time as president.

While history remembers the 1990s probe led by independent counsel Kenneth W. Starr for its pursuit of President Bill Clinton over the possibility he had lied under oath about his relationship with intern Monica Lewinsky, internal documents from the inquiry show how close prosecutors came to filing charges at that time against Hillary Clinton. They even drew up a draft indictment for Clinton, which has never been made public.

As in the email controversy of today, Clinton’s honesty was a central question facing investigators in 1998 as they weighed whether what they saw as shifting stories from Clinton amounted to an attempt to cover up misconduct. Like the events of today, Clinton was interviewed for hours by authorities. Unlike the email inquiry, in which Comey said Clinton’s status as a presidential candidate had no effect on the decision not to charge her, documents from the 1990s show how prosecutors weighed whether Clinton’s political popularity would make her more difficult to convict.

Nannygate, Travelgate, Whitewater, Filegate: it's tough to remember all the scandals that plagued then-President Bill and Hillary Clinton through the '90s. For millennials --- here's what you missed. For everyone else, here's a refresher. (Sarah Parnass,Adriana Usero/The Washington Post)

At issue then was legal work Clinton had performed in the 1980s while an attorney at Little Rock’s Rose Law Firm on behalf of Madison Guaranty Savings and Loan, which was owned by a business partner of the Clintons who was later convicted of fraud in connection with bad loans made by the thrift. Clinton said that her legal work was minimal and that she was unaware of the wrongdoing at Madison Guaranty.

The episode serves as a reminder of how long Clinton has faced scrutiny about her ethics and judgment, dating even to her days in the East Wing. It helps explain why public questions about her trustworthiness have been so difficult for her to overcome, as well as why she and her supporters have long felt targeted by their political opponents.

The records of prosecutors’ 1998 deliberations were obtained by The Washington Post from the National Archives through a Freedom of Information Act request. The Archives declined to release copies of the draft indictment to The Post, saying that access to the document is “restricted.” Judicial Watch, a conservative advocacy group, has sued the Archives, seeking release of the indictment draft.

The released records include a memo, written by Starr’s team, summarizing the evidence against Clinton. The prosecutors noted that she made numerous sworn statements between January 1994 and February 1996 that they thought “reflected and embodied materially inaccurate stories.”

“The question, generally, is not whether the statements are inaccurate, but whether they are willfully so,” the prosecutors continued.

The records show the prosecutors had doubts about whether potential jurors would be swayed by a largely circumstantial case, particularly given Clinton’s stature as first lady.

Prosecutor Paul Rosenzweig laid out the odds for various outcomes in a memo to colleagues. He predicted a 2 percent chance that a judge would toss the case, then continued: “18 percent = Acquittal; 70 percent = Hung Jury; 10 percent = Conviction.”


In this excerpt from a 1998 Office of the Independent Counsel memo, prosecutors outline the chance that they would get a conviction of Hillary vs. a hung jury or acquittal. (The Washington Post)

“Not enough in my view,” he wrote.

In an interview, Rosenzweig said he had reflected on that 18-year-old decision while listening to Comey’s remarks last week. He said Comey’s decision was “very reminiscent” of the challenge that faced the Office of Independent Counsel team.

Rosenzweig said he had concluded in 1998 that seating a jury untainted by political bias was going to be so difficult as to make the chances for a conviction too low to proceed ethically with the case.

“This case was, for me, decided on factors external to guilt or innocence,” he said. “I think this case would have had a great chance of a sustained conviction if presented to 12 random people, about someone other than Mrs. Clinton. But that’s an impossible hypothetical.”

A spokesman for Clinton, Brian Fallon, played down parallels between how prosecutors handled the present-day email inquiry and the Starr-led investigation in the 1990s.

“Then, as now, investigators were facing heavy outside pressure to generate a politically motivated prosecution,” Fallon said. “The difference is, in the case of the secretary’s emails, the Justice Department has resisted those partisan pressures, with career officials unanimously recommending that no case be brought. In the Whitewater investigation, which was not headed by career officials, the political forces exerted sufficient pressure to produce a bogus draft indictment — until, that is, the independent counsel’s office was forced to relent in the face of the facts and consign that draft document to the dustbin of history.”

The drama of the 1998 decision was laid out in the 2010 book “The Death of American Virtue: Clinton vs. Starr,” a definitive account of the Clinton impeachment saga by law professor Ken Gormley, who interviewed nearly all of the key players. Hillary Clinton did not speak with him.

Gormley wrote that prosecutors and FBI agents met to consider the matter at 8 a.m. on Monday, April 27, 1998, in a session that lasted until nearly midnight. The prosecutor who had led a four-year investigation of Hillary Clinton’s activities with the Rose Law Firm spent hours laying out for his colleagues the case that she had had more involvement in work that had facilitated illicit activity for Madison Guaranty and a troubled real estate project called Castle Grande than she had acknowledged.


The eyes of the news media are on Hillary Clinton as she arrives to testify before the Whitewater grand jury in 1996. (James M. Thresher/The Washington Post)

Prosecutors discussed one of the more dramatic moments of the Whitewater era: the unexpected discovery of billing records from Clinton’s time as an attorney in a storage room on the third floor of the White House residence .

The records had been missing for two years, and White House aides had said they could not be located, even after an exhaustive search, in response to a subpoena.

The records had been found in 1996 by Hillary Clinton’s executive assistant, on a table in a room adjacent to Clinton’s office. Clinton had told Barbara Walters in a televised interview that she was glad the records had surfaced, and she chalked their disappearance up to a White House crammed with millions of pages of disorganized documents. “You know, a month ago, people were jumping up and down because the billing records were lost and they thought somebody might have destroyed them. Now the records are found, and they’re jumping up and down,” Clinton said.

Starr’s team suspected that Clinton might have orchestrated the mysterious reappearance of the documents.

“There is a circumstantial case that the records were left on the table by Hillary Clinton,” the prosecutors wrote. The memo described how the lawyers had interviewed everyone else with access to the room where the records were found, then concluded: “She is the only individual in the White House who had a significant interest in them.”

Later in 1998, Starr told Congress that the discovery of the billing records was a “mystery” that his investigators had been unable to solve. In her 2003 memoir “Living History,” Clinton rejected the allegation that she had tried to hide the records. She wrote that she thought the documents had been lost until her assistant found them. “I certainly had no reason to conceal them and regretted that they had not been found earlier,” Clinton wrote.

Starr’s team also considered how Clinton probably would have had numerous advantages if a trial took place, as expected, in Arkansas or Washington, where jurors were likely to be supportive of the first lady.

Ultimately, instead of charging Hillary Clinton, the prosecutors decided to focus their energies on the Lewinsky issue.

Gormley, who is now president of Duquesne University in Pittsburgh, said his exhaustive review of the case led him to believe there was not a compelling case to indict Hillary Clinton. He said the April 1998 meeting occurred at a time when the investigation was otherwise stymied and that prosecutors, eager to make a case, considered the Hillary Clinton indictment as one of several strategies to potentially push it forward. “I got the sense that Starr prosecutors, generally, recognized there wasn’t sufficient evidence,” he said.

Rosenzweig, who is now a principal at a homeland security consulting company, said he continued to believe the group made the right decision not to seek an indictment. Still, he said he could remember leaving the all-day meeting “drained, disappointed, dismayed” that such a meticulous and lengthy part of the investigation had come to nothing.


An excerpt from a 1998 Office of the Independent Counsel memo showing some of the evidence investigators had gathered against Clinton, as well as the considerations that went into a decision not to file criminal charges against her. (The Washington Post)

Today, many Republicans are expressing similar frustrations about the FBI’s inquiry into Clinton’s email practices.

Comey has said he concluded that Clinton had been “extremely careless” in her handling of classified material but that there was no evidence she had broken the law by intentionally mishandling it. He insisted that her status as a famous former secretary of state, senator and first lady played no role in the decision.

That differs from the Starr prosecutors, who specifically weighed how her celebrity and political popularity might affect the jury in a criminal trial, Rosenzweig said. He said he does not think that Clinton personally has been afforded special treatment, now or in the 1990s — a charge often leveled by Republicans. But he said he thinks her case illustrates the way elites are generally treated differently in the justice system. “Our justice system is great — but it is imperfect,” he said.

In an interview, Gormley said Comey’s decision reminded him of a different episode in the Whitewater saga: the moment in 1992, not long before the presidential election, when Arkansas-based U.S. Attorney Charles Banks refused to reopen an Arkansas investigation that might implicate the Clintons. Banks told Gormley he had faced pressure from officials at a federal agency to do so but he refused, thinking the evidence did not warrant a probe, even though he would have benefited from the reelection of President George H.W. Bush, a Republican.

“Banks was very sensitive to the fact that if he were to get involved in this case again, with the presidential election looming so close, that would undermine the trust of the American public in our system of justice,” Gormley said of Banks. “Comey reminded me of that unsung hero.”