Joe Biden’s long history of friendships with segregationists in the U.S. Senate is suddenly emerging as a political issue after the presidential candidate this week fondly recalled working with two racists who were his fellow Democrats on Capitol Hill in the 1970s.

Through his nearly five decades in politics, Biden, 76, has praised or reminisced about working cordially with every major segregationist who served alongside him in the Senate, according to a Washington Examiner analysis based on a list of key segregation proponents compiled by the Equal Justice Initiative. In all, Biden has spoken warmly of or boasted about his ability to work with six men on the list.

He has lauded South Carolina Sen. Strom Thurmond — who Biden called “one of my closest friends” — and Sen. Jesse Helms of North Carolina, who Biden worked with on legislation to prevent court-ordered desegregation busing. He has also expressed admiration for Sens. John Stennis, James O. Eastland and Herman Talmadge. He has even praised George Wallace, an Alabama governor and segregationist presidential candidate.

Now, nearly 50 years after Biden was first elected to political office, all six men are dead, but the former vice president's wistful reminiscences of them over the years has suddenly brought them to the fore of the 2020 campaign. He worked with some of them to oppose busing (a way of forcing the desegregation of schools) and others on anti-crime legislation that disproportionately affected African Americans.

Biden’s fondness for these segregationists drew renewed scrutiny this week after he invoked two of his 1970s segregationist colleagues on the campaign trail, drawing condemnation from 2020 rivals Sens. Cory Booker and Kamala Harris, the only two black candidates among the 23 Democrats running.

Eastland, Biden said at a New York fundraiser on Tuesday, had "never called me ‘boy,’ he always called me ‘son.’” Talmadge was “one of the meanest guys I ever knew,” but “at least there was some civility. We got things done.”

W. Ralph Eubanks, a visiting professor of English and Southern Studies at the University of Mississippi who focuses on cultural and historical memory, said Biden appears to have a difficult time grasping the significant cultural shifts of the past few decades.

“He’s just out of touch with contemporary thought,” said Eubanks. “If you’re going to be attractive to this group of [younger] voters, who in some ways view themselves as almost advocates for a social justice movement, these past alliances that are antithetical to this point of view should not be examples that you bring up as examples of your political savvy."

"The way that we talk about race, class, and gender now with respect to Southern culture is very different than the way that Biden was thinking about it 40 years ago,” added Eubanks. "Is Biden nimble enough to play with cultural memory that way? I don’t think he is.”

Booker said in a statement, "You don’t joke about calling black men ‘boy.' Vice President Biden’s relationships with proud segregationists are not the model for how we make America a safer and more inclusive place for black people, and for everyone.” Harris told reporters, "Yes, it concerns me deeply. If those men had their way, I wouldn't be in the United States Senate and on this elevator right now."

While there appeared to be surprise at what Biden said this week, the former vice president has touted his friendships with segregationists in very similar terms for many years.

In Biden’s farewell address to the Senate, which he left in 2008 after 36 years there, he emphasized his “deep personal relationships” with segregationists. "I never thought I'd develop deep personal relationships with men whose position played an extremely large part in my desire to come to the Senate in the first place to change what they believed in — Eastland, Stennis, Thurmond,” said Biden. "All these men became my friends."

In 1988, Biden spoke to students at Clemson University, where he praised Sen. Strom Thurmond as one of his “closest friends," according to video first published last month by the Washington Examiner.

Thurmond was a staunch segregationist who opposed the Supreme Court's Brown v. Board of Education decision. While running for governor of South Carolina in 1948, he promised supporters: “[A]ll the laws of Washington and all the bayonets of the Army cannot force the Negro into our homes, into our schools, our churches and our places of recreation and amusement.”

In the 1988 speech, Biden said he admired Thurmond’s view that the U.S. is the “most heterogenous, diverse society in the world, and every point of view has to be accommodated.”

“If you had told me when I entered the United States Senate that one of the people that I’d have the closest relationship with in the Senate would be Strom Thurmond, I would have told you that you were crazy. And I suspect maybe Strom would have told you, you were crazy,” he added. “I’m not just saying Strom and I are close. Anyone who knows the Senate knows how seldom we agree on the controversial issues but how closely we work together.”

Biden said the Washington press would refer to him and Thurmond as the "marvelous marriage" and "the odd couple" and would often ask them how they got along. Although Thurmond never publicly renounced his comments on segregation, his friendship with Biden continued through the decades. In 2003, Biden gave a eulogy at Thurmond’s funeral.

Biden befriended Sen. Jesse Helms, who filibustered a bill to make Martin Luther King Jr.’s birthday a federal holiday and once proclaimed, “The Negro cannot count forever on the kind of restraint that’s thus far left him free to clog the streets, disrupt traffic, and interfere with other men’s rights.”

The then-Delaware senator worked with Helms to pass anti-busing legislation in the 1970s in an effort to stop the federal government from forcing public schools to desegregate by busing in students from different neighborhoods. In September 1975, Biden supported an anti-busing amendment to a federal bill proposed by Helms. Delighted by Biden's shift, Helms welcomed him "to the ranks of the enlightened.”

Biden also worked with West Virginia Sen. Robert Byrd, a former Ku Klux Klan recruiter who filibustered the Civil Rights Act of 1964 but later renounced his racist past, to push forward an anti-busing amendment in the 1970s. He gave a eulogy at Byrd’s funeral in 2010, calling the late senator the “dean of the United States Senate” and "a dear friend.”

Early in his career, Biden developed a close friendship with Stennis, the Mississippi senator who was a leading opponent of school desegregation and rejected the Supreme Court's order to integrate classrooms. In a 1988 letter, Biden told Stennis that he viewed him as a “hero” and was honored to move into his office after Stennis left the Senate, according to correspondence published by CNN.

"I have bittersweet feeling about moving into an office of such distinction. The bitterness relates to the knowledge that you will no longer be in the Senate and the sweetness to the knowledge that I will have a constant reminder of the man I viewed as a hero from the time," Biden wrote. "I sat next you at your conference table on my second day as a U.S. senator. You are a great man Senator Stennis and I will try to live up to the great and honorable tradition of the man who last occupied the office.”

In a 2016 speech in Pittsburgh, Biden discussed his fond memories of Eastland, a staunch segregationist who once said: “Those who would mix little children of both races in our schools are following an illegal, immoral, and sinful doctrine.” Eastland said before his death that he did not regret anything in his political career and “voted my convictions.”

Biden recalled that at the height of the desegregation busing debate, Eastland offered to help him win his reelection in Delaware. “I looked at Eastland. He said, ‘What can old Jim Eastland do for you in Delaware?’" Biden recounted. "I said, ‘Mr. Chairman, some places you’d help and some places you’d hurt.’ He said, ‘Well, I’ll come to Delaware and campaign for you or against you, whichever will help the most.’”

At a rally in Alabama in 2017, Biden said: “Even in the days when I got [to the Senate], the Democratic Party still had seven or eight old-fashioned Democratic segregationists. You’d get up, and you’d argue like the devil with them. Then you’d go down and have lunch or dinner together. The political system worked. We were divided on issues, but the political system worked.”

Talmadge, a vocal segregationist who died in 2002, once proclaimed, “There aren’t enough troops in the whole United States to make the white people of this state send their children to school with colored children.” Biden’s warm remarks about controversial Southern politicians was not confined to his Senate colleagues.

During his 1988 presidential campaign, Biden praised one of the most infamous segregationists in the United States, former Alabama Gov. George Wallace, and claimed that Wallace had given him an award in 1973 as one of the “outstanding young politicians in America.”

A representative for Biden's campaign did not respond to a request for the names of any segregationists who Biden had not enjoyed working with during his 47-year political career.