Mike Gravel, a Democrat who served two terms in the Senate representing Alaska and later ran for president, died on June 26 at the age of 91.

Gravel joined a crowded primary field of Democrats in 2006 to vie for the 2008 presidential nomination, announcing his bid at the National Press Club in Washington. After failing to gain traction, he made a bid for president as part of the Libertarian Party. He did not win that nomination either.

In the above CQ Roll Call archive photo from 1975, Gravel takes the oath of office from Vice President Nelson D. Rockefeller as Gravel’s family looks on.

Gravel made another bid for the Democratic nomination in 2020, but it didn’t last long and he ended up endorsing Vermont Sen. Bernie Sanders.

Elected to the Senate in 1968, he served two full terms but lost his primary race in 1980. Prior to federal office, he served in the Alaska House from 1962-1966.