Crossing the aisle: Joe Lieberman’s road from Kennedy Democrat to Connec

Crossing the aisle: Joe Lieberman’s road from Kennedy Democrat to Connecticut Independent

Friends and colleagues recall the late Connecticut senator’s political career from the Yale Daily News to the presidential campaign trail.

Published on April 1, 2024

When Joe Lieberman ’64 LAW ’67 arrived at Yale College in the fall of 1960, he was eager to make his mark on the institution.

Lieberman, an observant Jew educated in Stamford public schools, was admitted to the University in an era of quotas designed to limit Jewish enrollment. During his undergraduate years, the future Connecticut senator would serve as chairman — now called editor-in-chief and president — of the News, gain entrance to the senior society Elihu and forge relationships with Connecticut political leaders that allowed him to hand in a nearly 400-page biography of then-Democratic National Committee chair John Bailey as his year-long senior thesis. 

Lieberman, 82, died on Wednesday.

“Joe felt himself to be kind of an outsider in that world, the son of a liquor store owner, but he conquered,” said Robert Kaiser ’64, who served as the News’ features editor on the same managing board as Lieberman and later served as managing editor of The Washington Post.

A JFK Democrat

Kaiser met Lieberman in November 1960, when the two — then Yale first years — volunteered for the Connecticut Democratic Party to drive voters to the polls to elect President John F. Kennedy. Later, Kaiser encouraged Lieberman to join the News in the last of four “heeling” cycles — the process of becoming a News staffer, which was, at the time, a competitive process.

“There was no real student government at Yale in those days and the News was, in many ways, the most prominent activity on campus,” said Paul Steiger ’64, who worked on the News with Lieberman and later founded the news site ProPublica. “Joe wanted to have impact and so he heeled and he was an outstanding heeler and then he was elected chairman of the News.”

Lieberman’s college roommate, Richard Sugarman ’66, a professor of religion who served as an advisor to presidential candidate Bernie Sanders in 2016, recalled that Lieberman wrote with “efficiency and speed” unlike anyone he had ever seen. 

“It was the Civil Rights Era — people were marching, people were doing these things,” Jethro Lieberman ’64, another News editor who had no relation to the senator, recalled. “Joe had been a public high school student in Stamford. This was the Kennedy years, and that’s just where most of us on the News were.


Kaiser remembered that he and Lieberman ran against each other for the position of chairman, and Lieberman received every vote but one — Kaiser’s own.

Howard Gillette ’64, a managing editor for the News during Lieberman’s chairmanship, said that his near-unanimous selection distinguished him as an accepted leader among a class of highly accomplished News staffers. 

According to Gillette, Lieberman’s involvement in campus leadership led him to Mississippi in the fall of 1963 with a group of News staffers organized by University Chaplain William Sloane Coffin Jr. ’49 DIV ’56 to participate in the civil rights movement by campaigning for NAACP leader Aaron Henry.

Ahead of Mississippi’s 1963 gubernatorial election, Henry had organized the Freedom Vote Campaign, which rallied Black voters to participate in a mock election in which Henry was a candidate. The campaign’s goal was to combat disenfranchisement in the state by demonstrating Black voters’ desire and ability to vote. 

In a column published in the News titled “Why I Go to Mississippi,” Lieberman wrote that while the mock election was, to him, “not the most exciting” civil rights project, it represented an important effort to end the exclusion of Black Americans from elections.

“Our nation is emasculated as long as some of its rightful participants are excluded,” Lieberman wrote. “If I am able to carry across the concept of voting and the need for an all-out voter registration effort to 25 or 50 or perhaps 100 Negroes who have never been so confronted before, then I will return to New Haven with a sense of satisfaction. I go to Mississippi because I think this can be done.”

Lieberman’s Mississippi trip curiously resurfaced in 2006, when Connecticut State Treasurer Henry Parker questioned whether the trip — which the senator referenced in campaign speeches throughout his numerous electoral bids — had actually happened.

Gillette recalled that Lieberman’s campaign staff had contacted him about verifying that Lieberman had traveled to Mississippi. Gillette, who had not been on the trip, believed that Stephen Bingham ’64, a fellow News staffer who would later be tried and acquitted for suspected involvement in activist George Jackson’s escape from prison, would be the best source to confirm Lieberman’s participation. 

Bingham told the News that he does not recall Lieberman going on his trip to the South — at least not in the initial group of around 20 Yale students who traveled and attended training together.

However, according to Gillette, the reason Lieberman may have missed the first days of the trip was to orchestrate an activist stunt at the News.

As Yale College made small steps toward loosening their policy on including women on campus — namely, allowing women into the Linonia and Brothers reading room, which was then a gentleman’s lounge — the News published on its front page: “Girls Continue to Flood Admissions Office With Applications.” The article announced a rally for the upcoming weekend — Parents’ Weekend — outside Woodbridge Hall and encouraged visiting mothers to join in solidarity with women seeking admission.

According to Gillette, the women’s letter-writing campaign to admissions and the “boisterous” rally that followed were organized by Lieberman himself.

“It was the Civil Rights Era — people were marching, people were doing these things,” Jethro Lieberman ’64, another News editor who had no relation to the senator, recalled. “Joe had been a public high school student in Stamford. This was the Kennedy years, and that’s just where most of us on the News were.”

Lieberman rallies for women’s admission to Yale (Yale Daily News)

Throughout his tenure, Lieberman used his platform as chairman to develop and express his political opinions through his editorials, many of which expressed support for the ongoing civil rights movement.

Sugarman remembers that the only time he disagreed with Lieberman was when George Wallace, a pro-segregation governor of Alabama, was invited to speak at Yale in 1963. Lieberman defended Wallace’s right to free speech in a News editorial at the time. 

“The principle of free communication in an academic community is sacred and inviolable,” Lieberman wrote in the editorial. 

“Senator” at Yale

Lieberman was offered membership to Skull and Bones his senior year, but declined. Instead, he opted to join the Elihu Club, a senior society that eclipsed Bones as “cool and progressive,” according to Kaiser, who was also in Elihu. 

His autobiographical presentation — known commonly as a bio, one of Yale senior societies’ most storied traditions — focused on his upbringing in a “Jewish liquor store family,” the kind of background that was uncommon in the Yale circles Lieberman occupied, Kaiser said.

Jethro Lieberman, who was also in Elihu, recalled a society meeting where someone posed the question of what regrets each student thought they might have later in life, considering their intended career paths. 

“Joe looked at us and said, ‘Well, you know, depending on how things go, it would really be terrible if I wound up as mayor in Stamford, and then got run over by a truck,’” Jethro Lieberman said. “From the earliest days, it was clear that he saw himself in politics and moving up the political ladder.”

At Yale, Lieberman’s nickname was “Senator,” Sugarman said.

(Yale Daily News)

Always a fan of elections, Lieberman ran for class secretary in his senior year. He came in second, instead becoming class treasurer.

First steps in politics

As a senior in college, Lieberman was a “scholar of the house.” The now-defunct academic program, which selected up to a dozen Yale seniors each year, allowed him to work on a year-long project of his choosing instead of taking classes. 

Lieberman chose to write a biography of John Bailey, the then-chairman of the DNC who dominated the state’s politics, for his senior project. He later turned his work into a nearly 400-page book called “The Power Broker.” 

Michael Barone LAW ’69, Lieberman’s law school classmate who read the book, described it as “smartly objective and sometimes critical in a way that was really somewhat daring for someone with ambitions in Democratic politics in Connecticut.” 

“He got a lot of mileage out of it,” Jethro Lieberman added. 

Working on the book, Lieberman got to know many Connecticut Democrats, including former senator Abraham Ribicoff, who also served as Connecticut’s first and only Jewish governor. According to Jonathan Gruber, whose biographical film about Lieberman will premiere this year, Lieberman interned for Ribicoff in Washington during the summer of 1963 and saw him as a political role model.

Lieberman returned to the News in 2023 for the filming of Gruber’s documentary (Courtesy of Jonathan Gruber)

Lieberman matriculated to Yale Law School immediately upon finishing college and started practicing law in New Haven after graduating in 1967. 

In 1970, Lieberman, 27, successfully challenged incumbent State Senate President Ed Marcus in a Democratic primary. Lieberman spent the next 10 years representing New Haven in the Connecticut State Senate, including six as Democratic Majority Leader. 

“A lot of people in the Democratic Party weren’t so interested in having Lieberman go up against Marcus and so it was very hard for him to find volunteers,” Gruber said. “He went to the Yale Law School, and he found what he described as his ‘very affable fellow from Arkansas’ named Bill Clinton.”

Clinton LAW ’73 was one of several law student volunteers on Lieberman’s underdog campaign. 21 years later, Lieberman returned the favor, becoming the first Democratic senator to endorse Clinton’s presidential campaign, though he eventually became a fierce critic of the President during the Monica Lewinsky scandal.

In 1980, he left the State Senate to run for the U.S. House of Representatives in Connecticut’s 3rd district, which includes New Haven, but lost to Republican Lawrence DeNardis.

In 1982, he ran for Connecticut Attorney General. Gruber recalled that Matt Lieberman, Lieberman’s son, described the race as “make or break” for his father’s career: if Lieberman lost the race, he might have returned to law and forgone politics.

A lot of people in the Democratic Party weren’t so interested in having Lieberman go up against Marcus and so it was very hard for him to find volunteers,” Gruber said. “He went to the Yale Law School, and he found what he described as his ‘very affable fellow from Arkansas’ named Bill Clinton.

—Jonathan Gruber


Lieberman won, and he held the position for six years.

Taking the national stage

In 1988, Lieberman — still Attorney General — ran against Republican Sen. Lowell Weicker, a popular figure among Democrats for his tough questioning of President Richard Nixon as a member of the Senate Watergate Committee.

“Lieberman was very much a longshot candidate,” Steiger remembered. 

At the time, Steiger was a reporter for The Wall Street Journal, whose editorial pages leaned right. He recalled several conservative columnists endorsing Lieberman as Weicker increasingly voted against the Republican party line in Congress. 

Meanwhile, Lieberman had garnered a favorable reputation for his record as a consumer advocate during his tenure as Attorney General. 

One of Lieberman’s early supporters in the 1988 election was conservative writer William F. Buckley Jr. ’50, whom Lieberman had befriended at Yale through the News. Buckley created a political action committee, BUCKPAC, on Lieberman’s behalf, which sent donors bumper stickers with statements such as, “Does Lowell Weicker Make You Sick?” and “Republicans for Weicker? Yuck.”

Lieberman won the 1988 election by just 10,000 votes, upsetting the more liberal incumbent. He was reelected to the Senate three more times, including in 1994 with the largest-ever margin in a Connecticut Senate race and in 2006 as an independent after he lost the Democratic nomination. 

In the Senate, following the 9/11 terrorist attacks in 2001, Lieberman introduced legislation that led to the creation of the Department of Homeland Security. Senator Chris Murphy also credited his efforts to combat climate change for laying the groundwork for the 2022 passage of $369 billion in funding for climate and clean energy programs. 

As one of his last achievements in the Senate, Lieberman led a successful fight to repeal the “don’t ask, don’t tell” law, which banned openly queer people from serving in the military.

Former New Haven Mayor John DeStefano Jr. said that Lieberman had always been responsive to the needs of New Haven. He was a “local guy” in the city, DeStefano recalls, whom “you would see at Claire’s [Corner Copia].”

DeStefano said that when, in 2007, New Haven introduced the Elm City Resident Card for undocumented immigrants, the Department of Homeland Security started what he viewed as “retaliatory raids” in the city’s immigrant communities. 

“Joe got the Secretary [of Homeland Security] on the phone to me the same day,” DeStefano said, adding that Lieberman helped stop the raids in the city. “That’s what Joe was really good at —  responding to particular needs that affected people in their lives.” 

In August 2000, Democratic presidential nominee Al Gore picked Lieberman as his running mate. The Gore-Lieberman ticket, which won the popular vote by over 500,000 votes, lost the general election to Republican President George W. Bush ’68 and Vice President Dick Cheney after a recount and Supreme Court challenge in the crucial swing state of Florida.

Lieberman’s selection made him the first Jewish American to run for vice president on a major party ticket.

“They appreciated a man of faith, even though it wasn’t their faith.

—Jonathan Gruber


Throughout Lieberman’s political career, he maintained his Jewish observance.

Eden Migdal ’26, Lieberman’s granddaughter, recalled that Lieberman would walk home from the Senate with security personnel on Friday nights, declining to drive on Shabbat.

During his vice presidential campaign, Lieberman made repeated assurances that he would be able to balance his observance of Jewish custom with the demands of the office.

Gruber said that Lieberman’s observance was a significant help in his many elections in Connecticut, making him an appealing candidate to Catholic voters.

“They appreciated a man of faith, even though it wasn’t their faith, Gruber said.

In 2003, Lieberman announced his campaign for president. Running as a more conservative alternative to candidates Howard Dean ’71 and John Kerry ’66, the eventual nominee, Lieberman’s campaign announcement was attended by protesters from the group Jews Against Occupation, the News reported in 2003.

Emmaia Gelman, a member of Jews Against Occupation, a group that criticized Israel’s occupation of the West Bank and conduct toward Palestinians during the Second Intifada, was present at the protest. Gelman recalled her fellow organizers objected to Lieberman’s support of Israel, as well as the Iraq War.

“The Iraq War was absolutely important to us,” Gelman said.

A “stubbornly bipartisan” career 

Throughout his career in the Senate, Lieberman made conservative friends and often reached across the aisle in his work. 

He stood with his Democratic colleagues on domestic policy issues, like climate change, abortion rights and gay rights, but departed from them on foreign policy. 

In 2003, Lieberman, who consistently approved of American military interventions abroad, staunchly supported the Iraq War. He stood behind Bush as the president signed a resolution authorizing the invasion of  Iraq. 

(Office of Congressman Roy Blunt, Public domain, via Wikimedia Commons)

However, by March of 2006, 59 percent of Americans — and 77 percent of Democrats — believed that the US should set a timeline for withdrawing most troops from Iraq by 2008, according to a CBS News poll.

Later that year, Lieberman explained that while he wanted to end the war quickly, leaving Iraq at that time would be a “disaster” prompting sectarian violence. He also continued to affirm the correctness of his vote to authorize the war. 

When Ned Lamont SOM ’80, now the governor of Connecticut, launched his campaign to challenge Lieberman in the 2006 Senate race, he focused heavily on criticizing Lieberman’s record on the Iraq War and other cooperation with Republicans. 

“If you’re not going to talk about this administration’s failed foreign policy, failed fiscal policy, failed environmental policy and failed judicial policy, which are so harmful, then I will,” Lamont said at the time, blaming Lieberman for not being a “real Democrat.” 

In the 2006 Democratic primary, Lieberman lost to Lamont by a 3.6-percent margin. Instead of dropping out of the race, Lieberman decided to run as an independent candidate.

Lieberman’s decision to run against a Democratic nominee angered some Democrats in the state, prompting them to launch an unsuccessful attempt to expel the senator from the Democratic Party’s list of registered voters. Senate Democratic leaders Harry Reid and Chuck Schumer also supported Lamont’s candidacy, citing Lieberman’s “closeness to Bush” as the reason for his primary loss. 

The same year, Lieberman told The New York Times that his role as a senator required him to work with his colleagues on both sides of the aisle.

“I’ll tell you this: that doesn’t make me a bad Democrat, it makes me a better senator,” Lieberman told the Times.

Yale Daily News

(Yale Daily News)

In November, he won the general election with over 100,000 more votes than Lamont, becoming the first independent candidate to win a Senate seat in Connecticut since the emergence of the modern two-party system. Lieberman started his last term as a senator in January 2007 as an independent caucusing with Democrats. 

“When you have a long-term incumbent, the election really isn’t about party label or even about the opponent. It’s about whether people want to change or not,” DeStefano said. “I think it was a statement by the electorate saying, yeah, he’s doing a good job.”

Gruber speculated that Lieberman was blindsided by losing in the Democratic primary and that the loss contributed to his shift away from the party.

In 2008, Lieberman endorsed Republican John McCain, a long-time friend, in the presidential election and spoke at the Republican National Convention on McCain’s behalf. For some time, he even contemplated sharing the ticket as McCain’s running mate.

Tobias Kleinschmidt via Wikimedia Commons

In 2009, Lieberman clashed with Democrats on the Affordable Care Act. 

While Democrats debated President Barack Obama’s signature healthcare legislation, Lieberman came out in opposition to a government-run healthcare insurance option, or public option, even when its scope was reduced to Americans over the age of 55.

Rep. Rosa DeLauro, who represents New Haven, was a friend of Lieberman’s and endorsed his 2004 presidential campaign, which he cut short after disappointing results in early primaries. However, in 2009, when Lieberman opposed the public option, DeLauro called on him to step down from his Senate seat.

“I was angry at him and talked to him about it. We were dealing with potentially having a public option, and he came out in opposition to that,” DeLauro told the News. “I still believe it was the wrong policy. But I spoke to him and we have remained friends for many, many, many, many years.”

Lieberman eventually cast the 60th vote needed to pass the legislation, but his opposition to a public option forced Democrats to exclude it from the final bill. 

“When you have a long-term incumbent, the election really isn’t about party label or even about the opponent. It’s about whether people want to change or not,” DeStefano said. “I think it was a statement by the electorate saying, yeah, he’s doing a good job.”


By 2009, Lieberman had collected over $2 million in campaign contributions from medical professionals and insurers. The senator firmly denied that campaign finance influenced his vote.

Lieberman stepped down from public office in 2012 but remained politically engaged. In 2015, he became the founding chair of No Labels, a movement that aims to promote independent candidates for federal office. Recently, the group has gained prominence for its attempt to find an independent candidate to run in the 2024 presidential election. No Labels announced in early March that it intends to field a 2024 presidential ticket.

Kaiser remembered sending the senator a “stern email” expressing concern with Lieberman’s latest involvement in No Labels, which Kaiser believed would help former President Donald Trump, the presumptive Republican nominee, win in November. 

“Like many others, he did not wrestle with the profound change that has occurred in the Republican Party in our lifetime,” Kaiser said. “He couldn’t cope with it intellectually or emotionally. The idea that Republicans had become the anti-government party was just too much for him to deal with.”

A legacy of “likable decency”

Lieberman figures prominently in Howard Gillette’s 2015 book “Class Divides: Yale ’64 and the Complicated Legacy of the Sixties,” which charts the formative convergence of the Kennedy presidency, the civil rights movement and the opportunity of a Yale education in the lives of Gillette’s classmates.

For Gillette, no member of the class of 1964 better exemplified a determination to reconcile the clashing perspectives that emerged from the ’60s than Lieberman. 

“He found it troubling to end his political career outside the party of John Kennedy. For years he had been buoyed by the company of others he considered centrists like himself,” Gillette wrote in the book. “Like Ronald Reagan before him, Lieberman felt at the end of his career that he had not left the Democratic Party so much as it had left him.”

Jethro Lieberman also said that the Senator did not become more conservative over the years, but instead, labels changed. 

Kaiser, on the other hand, believes that Lieberman’s views shifted dramatically over time. He said that Lieberman’s “departure” from the liberalism of his youth was exemplified by his support for McCain in 2008.

“Joe, in the early ’60s, was a Democrat and convinced liberal,” Kaiser said. “If I told Joe in 1962 that in 2008, he will be supporting a conservative super-hawk Republican president over the first Black American president, a liberal Democrat, he would not have believed it.”

Kaiser clashed with Lieberman over the years, occasionally approaching the senator about the policy choices that seemed so discordant with his past views. While Lieberman hated to be disagreed with, Kaiser recalled, he never got angry — an observation that Migdal also shared.

“Like Ronald Reagan before him, Lieberman felt at the end of his career that he had not left the Democratic Party so much as it had left him.”

—Howard Gillette ’64


Upon his death, Lieberman’s political contemporaries, including Lamont, DeLauro and Sen. Richard Blumenthal LAW ’73 released statements acknowledging their disagreements with the senator but affirming respect and gratitude for years of public service.  

When asked by the News about Lieberman’s legacy, Kaiser, his college friend and longtime peer, emphasized his character over his policy accomplishments. 

“Will he be remembered at all? Yes, he will,” Kaiser said. “Because he was the first Jewish candidate for vice president and because he was an extremely decent person who everybody liked. He’ll be a symbol of likable decency, that might survive for a while. But his contributions were temporal, temporary.” 

The Yale College class of 1964 will celebrate its 60th reunion in May.


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