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Ulysses S. Grant was the only President to have two Chief Justice nominations opposed by the Senate. Both candidates' names were withdrawn prior to a vote due to indications the men would be formally rejected:

George Henry Williams (1873)

The Senate Judiciary Committee declined to recommend Attorney General Williams to the full Senate. He was later forced to resign as Attorney General when caught accepting a $30,000 bribe from Pratt & Boyd in exchange for dropping charges of fraudulent customs entries against the company.

Caleb Cushing (1874)

Cushing's nomination was withdrawn when he was strongly criticized for his earlier anti-war stance and inconsistent behavior when serving in the US Senate. On one or more occasions, Cushing publicly supported causes he later voted against.

Others Rejected as Chief Justice

John Rutledge, (1795) Rutledge was a recess appointment by President Washington, but the Senate believed he was mentally incompetent and declined to confirm his nomination. Rutledge attempted suicide when he learned of the rejection.

Roger B. Taney, (1835) Andrew Jackson's nomination of Roger B. Taney for Chief Justice was tabled indefinitely, but he was ultimately confirmed when the political composition of the Senate changed a few months later.

Abe Fortas, (1968) President Johnson nominated Abe Fortas to replace Chief Justice Earl Warren, who was planning to retire, but conservative members of the Senate saw him as an extension of Warren, whom they disliked due to his progressive leadership. Fortas also raised eyebrows by accepting a total of $15,000 from corporations in exchange for public speaking engagements at universities. The Senate filibustered Fortas' nomination, and his supporters weren't able to muster enough votes for cloture. Fortas was forced to resign in 1969 after accepting a $20,000 retainer for legal advice from a friend and Wall Street financier.

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Q: Which US President had the most unsuccessful nominations for appointing Supreme Court Chief Justices?
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