When Barack Obama was elected the 44th U.S. president in 2008, he was the first African-American man to win the office. Whenever anyone runs for president, their personal and public record is examined carefully, by their political opponents but also by the public and by the press.

Through this process, things are sometimes brought up from a candidate’s past that they might rather be forgotten. Such was the case when in 2008 Obama’s disputed potential connection to a radical ’70s-era leftist organization called the Weather Underground first came to national attention.

Prior to winning the presidency, Obama’s home base was in Chicago. His career in politics began in the Illinois State Senate before he represented the state as a U.S. Senator.

Prior to his career in politics, Obama taught law at the University of Chicago law school, as Biography notes. Also a member of the University of Chicago faculty was Bill Ayers, a founder of the radical leftist and anti-Vietnam war organization called the Weather Underground.

In 1975, the Weather Underground claimed responsibility for a violent explosion in the U.S. State Department in Washington, D.C. No one was hurt, per the FBI website. 

During the 2008 campaign, a relationship between Obama and Ayers surfaced. This news nearly derailed Obama’s presidency.

What was the Weather Underground?

Also called the Weather Underground Organization, the Weather Underground was first founded in 1969 as the Weatherman, per Britannica.

At that time, the controversial war in Vietnam was raging, and similar organizations were forming across the U.S. to oppose the conflict. Rooted in Marxist philosophy, the core tenets of these organizations were often anti-war and anti-imperialist.

Some groups chose peaceful means by which they sought to attain these goals. Others chose direct action, confrontation, and violence. For their part, the Weather Underground chose the latter, beginning in 1969 when members of the group attacked teachers and professors and gave inflammatory radical speeches at schools in the northeastern U.S.

These aggressive and violent tactics naturally drew the attention of law enforcement agencies. As a result, the Underground had largely gone off the radar by 1970.

Due to Bill Ayers involvement in the Weather Underground, he lived as a fugitive for a number of years before charges against him were dropped and he once more resurfaced. After that point, Ayers (pictured) wrote books and taught law at the University of Chicago, where Obama was also a law professor.

When Obama’s potential relationship to Ayers was revealed, Obama characterized it as if they knew each other only in passing (via The Hill). Research performed during Obama’s 2008 presidential campaign uncovered evidence, though, that might not be the full story.

The Obama and Bill Ayers connection

When pressed on the nature of his relationship with one-time wanted fugitive and left-wing radical activist Bill Ayers, Obama said (via The Hill) that Ayers was “a guy who lives in my neighborhood,” adding that he was not someone Obama exchanged “ideas with on a regular basis.”

Deeper examination into documentation at the Richard J. Daley Library at the University of Illinois at Chicago, though, proved both Obama and Ayers served on the same charitable boards. A fundraiser and kickoff for Obama’s 1995 run for the Illinois state Senate also took place at Ayers’ home. 

After Obama was elected for a second term, both he and Bill Ayers even attended the same wedding, as The Hill reports. When pressed on any potential conflict or influence Bill Ayers may have on his thinking, Obama said (via The Hill) “[T]he notion that somehow as a consequence of me knowing somebody who engaged in detestable acts 40 years ago — when I was 8 years old — somehow reflects on me and my values doesn’t make much sense.”

Bill Ayers disapproved of Obama’s presidency

Regardless of the true nature of Barack Obama and Bill Ayers relationship, Obama won the presidency twice, in 2008 and again, in 2012. Although Ayers admitted he liked Obama as a person, he also made clear that he disagreed with Barack Obama’s policies in several instances.

Via an interview with Real Clear Politics in 2013, Ayers even said he believed Obama should be put on trial at the Hague for war crimes over drone strikes. At that point the academic also gave the Obama administration a failing grade.

“Every [U.S. president] goes into office, an office dripping with blood, and adds to it,” Ayers said. “Every president in this century should be put on trial, every one of them … For war crimes. Absolutely,” Ayers continued. 

The Weather Underground once more made headlines in 2022 when it was announced that Kathy Boudin died from cancer at the age of 78. Boudin was a former Weather Underground member who spent time in prison for an armored truck robbery during which three people were killed (via The Guardian).