[1] His parents were Lilian (née Edelman) and Samuel Benson, who owned a showroom for Studebaker automobiles in Washington Heights.

[3] In 1933, Benson was one of 20 students expelled from the City College of New York, for participating in an anti-war protest against the campus ROTC during his sophomore year.

[9][10][11] Working with Socialist leader Norman Thomas, Benson organized an ad hoc legal fund for activist Marion Cieply and Irwin Rappaport, a shop steward.

[8] Although the lawsuit was eventually dismissed because the events had taken place before the LMRDA, also known as the Landrum–Griffin Act, had been passed, the case marked the start of a decades-long collaboration between Benson and Summers.

[8] Legal scholar Michael J. Goldberg wrote, "Clyde Summers and Herman Benson spent the rest of their careers working together as the leading figures in the union democracy movement, with Summers providing the legal expertise and Benson providing the street smarts, organizing and fundraising skills, and willingness to work for a pittance".

[10] Benson independently confirmed the allegations, and organized support for Schonfeld as he ran for union president, lost, and was expelled, until his expulsion was overturned in court.

[10] Despite their initial successes in working with Schonfeld and others, the shocking murders of several union dissidents and reformers convinced both Benson and Summers that more needed to be done to protect them.

[10] Following the murder, Benson sought publicity for Wilson's story, which was broken by Frank Porter in a major four-part series in The Washington Post.

[12][10] Working again with Norman Thomas, Benson helped coordinate a committee of 21 co-sponsors calling for a full investigation by the United States Department of Justice into the two murders and racketeering in the painting industry.

[12] In 1969, Benson founded the Association for Union Democracy (AUD), a non-profit organization, and asked Summers to join as an active member of its Board of Directors.

[1] In Benson's own obituary, which he wrote himself in the third person prior to his 100th birthday,[1] he quipped that "his last, dying words" were: "This is the time for a donation to the Association for Union Democracy.