The Volokh Conspiracy
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Today in Supreme Court History: November 12, 1975
11/12/1975: Justice William O. Douglas resigns.

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Douglas made his name as a trustbuster at the end of FDR's second term. He clearly had his eye on the White House, so Roosevelt, who didn't like men with a lean and hungry look, appointed him to the Supreme Court, an offer Douglas couldn't quite turn down. (Roosevelt did the same thing with James Byrnes, who eventually resigned from the Court because he found it too boring.) According to Ronald Radosh's famous book on the Rosenbergs, Douglas, though aggressively "left", was also strongly anti-communist, and for a long time refused to intervene in the Rosenberg case because he felt the communist party wanted the Rosenbergs to be martyrs, and the party's whole legal strategy was to accomplish that goal. Later, according to Radosh, he changed his mind, but the rest of the Court, except (unsurprisingly) Frankfurter, the lone Jew on the Court, "rammed through" the Rosenbergs' execution in collusion with Attorney General Brownell.
Probably the most inept legal mind ever to sit on the Court. No justice ever cared less about doctrine, or giving plausible guidance to lower courts, lawyers, and clients, or creating rules that would be workable, than Douglas.
At the time Roosevelt appointed him he wanted results not reasons, and he got what he wanted.
He would have resigned right after his stroke but the Congressman who had tried to impeach him (Gerald Ford) was now President and would pick his successor.
As for his opinions, he was considered left wing, but most Americans now agree with them.