After Hillary Clinton clerked in the summer of 1971 at an Oakland, Calif., law firm run by attorneys with ties to the Communist Party, she never returned to work there. But she stayed in touch with one of the firm’s partners and his wife, and they stayed in touch with her, until they died. The decades-long correspondence illustrates the complicated relationship between Mrs. Clinton and radical activists who were often frustrated by the failure of Mrs. Clinton and her husband to side with them.

Much of the correspondence concerns a crisis that Bill Clinton faced involving the Arkansas prison system soon after he became governor in 1979. Hollywood, the courts, and liberal activists joined forces to pressure Mr. Clinton over allegations that inmates in Arkansas were subjected to inhumane conditions and that guards were corrupt and abusive. The campaign’s centerpiece was a movie, “Brubaker,” which starred Robert Redford as an Arkansas warden bent on reform.

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One key player in the tumult over the Arkansas prisons was a satirical writer, social critic, and former Communist, Jessica Mitford. The daughter of a British baron, Mitford was the wife of Robert Treuhaft, one of the founding partners of the firm where Mrs. Clinton summered in 1971, Treuhaft, Walker and Burnstein.

Mitford, best known for her 1963 exposé of the funeral industry, “American Way of Death,” was also a civil rights activist who had long decried American prisons and the justice system in the South. In 1980, she seized on the case of an Arkansas prison escapee, James Dean Walker, who had been convicted at two separate trials of the murder of a Little Rock police officer during a traffic stop in 1963. Walker, who became a born-again Christian in prison and won furloughs for religious work, failed to return from one of those sojourns in 1975.

Walker fled to California, where he took up residence near Lake Tahoe. In 1979, he was arrested on drug charges. Arkansas officials soon moved for Walker’s extradition back to Arkansas.

Walker’s California lawyers tried to block his return, arguing that Arkansas prison conditions were unconstitutionally cruel and that he faced particular danger because a warden had threatened to kill him. Walker also argued that he had been wrongly convicted.

For left-wing activists, Walker’s challenge to his extradition represented a chance to call attention to prison conditions across the South. Mitford decided to try to leverage her husband’s ties to Mrs. Clinton to get Arkansas to drop the extradition or to pardon Walker outright. Despite an aggressive campaign, including a personal visit Mitford paid to Little Rock, the Clintons did not budge. Mitford, who clearly expected a different response, later described the episode as a “furious falling-out.”

How close Mrs. Clinton was with Treuhaft and Mitford prior to the Walker case is not clear. Mitford died in 1996; Treuhaft, in 2001. Mrs. Clinton did not respond to requests for an interview for this article.

James Dean Walker in 1967 (Source: Arkansas Democrat-Gazette).

A handwritten note Mrs. Clinton sent Treuhaft in November 1979 suggests that she had little contact with him after her clerkship in Oakland in 1971. “Yes, it’s all true. I’m alive, reasonably well, and living in the Governor’s Mansion,” Mrs. Clinton wrote. She said she hoped to have a chance to visit during an upcoming board meeting in San Francisco of the Legal Services Corporation. She never did.

According to Mitford’s papers, which are housed at Ohio State University, she and Treuhaft first raised the Walker case with Mrs. Clinton in February 1980, by copying the former law clerk on a telegram the couple sent to an aide to the governor of California. The governor, Edmund Brown Jr., had announced plans to proceed with the extradition of Walker without a formal hearing, despite the prisoner’s claim that he was likely to be killed if sent back to Arkansas.

“Tom Murton former head of the Arkansas prison system, is prepared to testify that Walker would be in mortal danger if returned to Arkansas penitentiary, condemned by federal court for cruel and unusual punishment,” Treuhaft and Mitford wrote.

Mrs. Clinton didn’t answer right away. In the meantime, the legal maneuvering intensified. On April 9, 1980, the California Supreme Court halted Walker’s extradition until a judge in California’s El Dorado County, near Lake Tahoe, could conduct a hearing on the conditions of Arkansas prisons. The decision threw the young governor of Arkansas into a rage.

“I am so angry,” Mr. Clinton said, according to quotes Mitford gleaned from press clippings. “Who do they think they are — are we under their jurisdiction? It’s just outrageous. We’re going to fight this action until the last dog is hung.”

Mrs. Clinton’s reply to Treuhaft and Mitford came more than two months later, in the form of a three-page letter typed on the letterhead of the Little Rock, Ark., corporate law firm where she worked, Rose Nash Williamson Carroll Clay and Giroir. The first lady of Arkansas opened with pleasantries.

“I am sorry I was unable to visit with you in December in California,” Mrs. Clinton began. “I am hoping that I will have another opportunity to travel to the Bay Area and that we will have a chance to visit. Since my trip West, Bill and I have had our first child, a daughter, Chelsea Victoria, and our lives are pretty much occupied with the challenges she offers.”

Mrs. Clinton went on to argue, in rather sterile detail, that the state had remedied most problems with its prisons, thanks largely to Mr. Clinton’s work as attorney general and then as governor. She cited new accreditation for the prisons, a new infirmary, staff training, pay raises for guards, and an end to the use of trailers for inmate housing.

Mrs. Clinton also hailed the hiring of a compliance coordinator to review prisoner complaints and obedience to federal court orders. “It is hoped that this mechanism will be the catalyst for removing the stigma of unconstitutionality from our system by March, 1981,” she wrote. “I could go on and on with the many changes that have taken place in just the last few years and the ones that are scheduled for the very near future, but I think I have shared enough with you to prove my point. The Department of Corrections that existed in 1970 is no longer present in Arkansas.”

Mrs. Clinton closed by curtly dismissing Walker’s assertions of danger. “I do not know how Mr. Walker’s claims will be resolved, but I really believe they are without merit,” she wrote. “Cordially yours, Hillary.”

Mitford was not impressed. In a letter to one of her editors, she dismissed Mrs. Clinton’s reply as “essentially a form letter prepared in response to numerous inquiries about the Walker case, but hedged round with personal bits of news.”

The day after Mrs. Clinton sent her letter, a Supreme Court justice, William Rehnquist, stepped in and blocked the California courts’ attempt to assert jurisdiction over Arkansas jails. “The proper forum for respondent’s challenge to Arkansas prison conditions is in the Arkansas courts,” Rehnquist wrote. (Later that year, the Supreme Court ratified Rehnquist’s action, though one justice, Thurgood Marshall, complained that the court had given short shrift to Walker’s complaints.)

Mitford’s wit shined through in her initial response to Mrs. Clinton in May 1980. “Thanks so much for your very interesting letter re changes in the Arkansas Prison System, from which (as you put it) the ‘stigma of unconstitutionality’ should be removed by March, 1981,” Mitford wrote, adding tartly, “Which, of course, might seem a rather long time to those confined in the prisons.”

Mitford asked why Mrs. Clinton had not addressed the claims of various people that Walker would likely face harm if put back in the Arkansas prisons. “I wonder if you or anybody in the Governor’s office ever got in touch with these people re their proposed testimony?”

After receiving no reply, Mitford sent another letter in June, saying “what I really want is an answer.” Pivoting to the personal again, Mitford asked, “Chelsea Victoria—what a marvelous name! How did you come by it? Was she conceived in Victoria Station, or Chelsea?”

The editor of a book of Mitford’s letters, Peter Sussman, said it seemed Mitford was trying to take advantage of a “non-existent” friendship with Mrs. Clinton. “She sort of made it as personal as she could try to inveigle some cooperation,” the editor said.

Mrs. Clinton’s response, handwritten over two pages about three weeks later, begins with an apology for her tardiness and a quip about her infant daughter’s appearance. “I find motherhood incredibly absorbing. I never imagined I’d be as captivated as I am. Chelsea Victoria looks distressingly like Winston Churchill which at least diverts inquiries as to why we named her after the London Subway,” the Arkansas first lady wrote.

As Mrs. Clinton recounted the negative publicity Arkansas was getting from “Brubaker,” she began to bristle a bit.

“Probably no other prison system has received the careful scrutiny Arkansas has since 1968. The remaining deficiencies are serious and need correction, but they are not the type for which the State became infamous,” she wrote. “I don’t believe you, or Bill or me will be satisfied with prison conditions here or elsewhere in the country for the foreseeable future, especially with Reagan in the White House and the resurgence of reaction.”

Reagan, who was about to receive the Republican nomination for president, would not be elected until four months later.

“But,” Mrs. Clinton added, “it is inaccurate for anyone … to talk about the Arkansas system today as being no different from the one of ten or even five years ago.”

Mrs. Clinton also said she talked with one of Walker’s allies who said he thought the convict’s fears of harm were “genuine.” “Based on what I know about the people now running the system, I dispute the factual basis of such feelings and do not believe Mr. Walker’s position is meritorious, although it is ingenious,” she wrote, displaying some of her own acidity. She signed the note, simply, “H.”

A few days later, the wave of national publicity over “Brubaker” and the Walker affair reached a crescendo. On July 24, 1980, Mr. Clinton appeared on NBC’s “Today” show to defend the state’s prisons and the handling of the Walker case

Mitford, known to friends as Decca, was undeterred by the Clintons’ rebuffs. She obtained a commission to write an article about Walker for New West magazine, which was owned at the time by Rupert Murdoch but sold before the story ran.

Flashing her communist-atheist roots, Mitford promised to softpedal Walker’s jailhouse conversion. “Walker, alas, is a born-again Christian,” she wrote to her editor at the magazine. “Oh well can’t win ’em all. I shall DOWNPLAY this distressing aspect of our hero.”

Within days, acting as both journalist and advocate, she flew to Arkansas to talk to the Clintons and visit the prisons. “I feel I have entrée into the Gov’s mansion in Ark., in a way, if only to cuddle Chelsea Vict.,” Mitford wrote to a friend, “Kay,” possibly Katharine Graham of the Washington Post.

On August 1, 1980, Mitford interviewed Mr. Clinton in Little Rock. According to her notes, the governor insisted that Walker would be safe if returned to Arkansas. “No one takes the threats lightly, but prisons are under totally different leadership. We’d go on assumption Walker’s fears are genuine, but there would be no opportunity to carry out the threats,” Mr. Clinton said.

Asked why the warden who allegedly threatened Walker, Arvie Lee Lockhart, was still running a prison despite repeated allegations of brutality against him, Mr. Clinton hedged, neither endorsing nor condemning the warden. “Lockhart is seen by a majority of the Board of Corrections—who are in charge of everything — in charge of the hiring and firing — as a link of stability running through the prison. He has strong support by numerous legislators, they think he’s held the prison together,” the governor said. (Mr. Lockhart was later indicted on federal fraud charges related to prison contracting, but the case was dismissed in a deal that put the former warden on a form of probation.)

In the interview with Mitford, Mr. Clinton again scoffed at Walker’s legal argument that he should be permitted to challenge Arkansas prison conditions from outside the state. “If the claim is upheld in the U.S. Supreme Court — think of the consequences! Escapers would flock to California,” the governor warned.

Mr. Clinton rejected Mitford’s suggestion that Walker’s alleged rehabilitation while on the lam might be grounds to drop the extradition. However, the governor offered one concession: he said it might be possible for Walker to serve out his sentence in a California prison.

After Mitford returned to California to finish the article, she got a letter from a prominent Arkansas attorney and judge who had overturned Walker’s first conviction and was dubious about the evidence in the case, Oscar Fendler. Fendler said that when he pressed Mr. Clinton about dropping Walker’s extradition, the governor asked “how the public would react to him favoring a cop killer.” Fendler, who died in 2002, wrote that he replied by stating his view that Walker was innocent. The lawyer later sent Mitford a letter predicting that Mr. Clinton would win re-election “by a very large margin.” Fendler, who copied the letter to Mrs. Clinton, warned that her husband should “quit thinking about his ambitions to be President of the United States and perform his duties day by day.”

In November 1980, Mr. Clinton, who was the youngest governor of an American state in four decades, experienced a searing defeat at the hands of a little-known Republican challenger, Frank White. Walker’s supporters were stunned, but lost little time. They hoped that the lame duck governor might pardon Walker before leaving office. Mitford urged enlisting an actress friendly with Walker and the Clintons, Shirley MacLaine. Mr. Clinton left office without taking any action, but Walker’s backers didn’t give up.

Walker was eventually returned to Arkansas. During a federal court hearing on his bid to be housed out of state, both Clintons were called to testify about promises allegedly made about Walker’s safety.

Walker’s lawyer at the time, Bill Bristow, said in an interview recently that he couldn’t recall precisely what information Mrs. Clinton was thought to have about the purported pledges. “I examined both of the Clintons and found Hillary to be a very, very tough witness to deal with. She gave me nothing,” Mr. Bristow said. He remembers Mitford attending a later hearing, along with an actor who was pitching a television movie about the case, Mike Farrell, best known for his role on “M*A*S*H.” “All I knew was these famous people were coming into Arkansas and supporting Mr. Walker,” Mr. Bristow said.

Mitford’s papers show she pitched the story repeatedly to television personalities, such as Phil Donahue and Geraldo Rivera, then with ABC’s “20/20.” She also unsuccessfully urged the NAACP to step in, even though Walker was white. The swirl of outside attention may have contributed to polarized opinions about the Walker case. “Some people thought, ‘Well, this is just a cop killer.’ And a lot of people thought he was, in fact, innocent,” Mr. Bristow recalled.

Mr. Bristow said the Clintons didn’t seem to approach it from that angle. “It was really an issue of the pride of Arkansas,” the convict’s lawyer said. “I never had a discussion with Hillary Clinton about whether Walker was guilty or innocent … Bill Clinton, in my opinion, had an open mind on that subject.”

Mitford’s efforts may have helped Walker at times, but she had trouble hiding her condescension towards Mr. Clinton’s home state. In a letter to Walker, she said she passed up writing a book on Walker’s plight because “it would mean weeks, if not months, spent in dread Arkansas.” In another note, she called the state “backward.”

Walker was ultimately ordered jailed outside Arkansas, at a prison in El Reno, Okla. His campaign to assert his innocence went on, though the Clintons seemed to recede from the picture. In 1984, the full bench of the 8th Circuit Court of Appeals voted, 5–4, to reject Walker’s demand for a new trial. A year later, following publicity about new evidence in the case, a judge on the court with close ties to the Clintons, Richard Arnold, reversed himself, joining a 5-4 ruling that overturned Walker’s conviction.

State officials and police were outraged by the decision. In 1986, a third trial was averted when Walker pled guilty to manslaughter and was set free based on his time served.

Supporters said they expected Walker would prove his rehabilitation was a success. He made his way back to Lake Tahoe, where he worked shining and repairing shoes in a casino. Within a matter of months, Walker was again in trouble with the law, arrested during a cocaine sting. The arrest appeared to be a blow to Mitford and others who vouched that Walker was a changed man.

Yet the Walker tale had one more twist. His ever faithful Hollywood friends funded a defense, in which Walker argued that he was entrapped by a female agent, who “really cozied up to him,” the defense lawyer, Philip Kohn, recalled. There were also suggestions that Walker was targeted by police seeking to settle scores from Walker’s Arkansas days.

To the surprise of Mr. Kohn, Walker was acquitted based on the entrapment defense. “It never works. It did work in that case,” the lawyer said.

Walker, 67, now lives in Boise, Idaho. The judge who wrote the appeals court opinion that eventually set Walker free, Myron Bright, now lectures about the case and keeps in touch with Walker. “He calls me every Christmas and thanks me for giving his life back,” Judge Bright, 88, said.

While Walker won his freedom in 1985 by the vote of a single jurist, Judge Bright noted that under current law there would probably have been nothing he could do to help the convict. “As I understand it, it would be impossible to get a successive habeas on the same grounds today,” the judge said.

In 1996, Congress passed a law setting a one-year time limit for filing a habeas petition and making it very difficult to file more than one, as Walker did. The statute, the Antiterrorism and Effective Death Penalty Act, was signed by President Clinton, the judge noted.

By the time the Clintons gained national prominence during Mr. Clinton’s presidential bid in 1992, Mitford seemed willing to let bygones be bygones. In a letter to a friend that year, Mitford wrote “in 1980, I had a furious falling out with the Clintons and Jerry Brown. It concerned the extradition to Arkansas of an escaped convict who had lived for 4 1/2 blameless years in California.”

However, Mitford went on to give a strong endorsement to Mrs. Clinton. “From all, I know about her Hillary seems to be an excellent person,” the writer said, adding that she agreed with a friend who deemed the future first lady “smashing.”

Mitford’s files also show she came to Mrs. Clinton’s defense after an article in Harper’s Magazine scored the future first lady over her views on legal rights for children. Mitford sent Harper’s a letter calling the article “a lot of campaign claptrap, hardly worth bothering with” and “a wild leap of … imagination supported nowhere in the articles and speeches of Hillary Clinton.”

In March 1993, Mitford wrote Mrs. Clinton, saying the last time they met Chelsea was in a high chair. Mitford urged the first lady, then immersed in the health care issue, to consider lay midwives and a single-payer plan. Mitford also lamented negative articles on the Clintons appearing in the British press. “I was a bit appalled at that ghastly creature Murdoch doing Bush’s dirty-tricks work from afar,” she wrote.

For her part, Mrs. Clinton sent Mitford’s publisher a note of thanks in December 1992 for a copy of Mitford’s new book, “American Way of Birth.”

“I am an admirer of Jessica Mitford and appreciate you thinking of me in this way,” Mrs. Clinton wrote.

In 1996, when Mitford died of cancer, Mrs. Clinton sent a handwritten condolence note to Treuhaft. “Everyone who knew Decca will miss her humor, wisdom and pointed observations about life — and about the rest of us,” the first lady wrote.