Which President’s Supreme Court nominee was the first to fail Senate confirmation?

The first Supreme Court nominees who failed to make it through Senate confirmation were both nominated by President George Washington.

The first Supreme Court nominee who was not confirmed was William Paterson, nominated by President George Washington. Washington withdrew the nomination on the day following its submission. He noted that Paterson was a member of the Senate when the law creating that office was passed, and that the time for which he was elected had not yet expired. For this reason, President Washington felt that this nomination was in violation of the Constitution. President Washington re-nominated Paterson at the beginning of the next Congress a few days later, and Paterson was immediately confirmed. In this case, the failure of the first nomination was due to what might be considered formalities, rather than opposition to the nomination itself.

President Washington's 1795 recess appointment of former Associate Justice John Rutledge to Chief Justice failed to win Senate approval due to an ill-timed speech by Mr. Rutledge in which he vehemently opposed a controversial treaty with Great Britain.

President Washington's nomination of John Rutledge to Chief Justice, in 1795, was the first unsuccessful nomination to fail based on the nominee's political views.