Caleb Cushing has the dubious distinction of being blocked by the Senate from presidential appointment more than any other person in the history of the United States. Cushing was rejected not once, not twice, but four times.
Cushing was nominated to become President John Tyler's treasury secretary in March 1843. Both men faced stiff opposition. Tyler had broken with the Whig party that had elected him to the presidency two years earlier, and the Whigs controlled the Senate. Cushing was himself a member of the House and had alternately supported, then voted against, Tyler's anti-Whig vetoes. Not amused with his flip-flopping, the Senate voted against Cushing's nomination. Tyler resubmitted Cushing as his treasury nominee, and again it was defeated. Later that same day, Tyler again resubmitted Cushing's name, and again, the Senate rebuffed him -- for the third time in a single day
Unfortunately, Caleb Cushing's streak of political bad luck would continue. Thirty years later, President Ulysses S. Grant nominated him for chief justice of the Supreme Court. This time, it was the Republicans who sunk him by leveling allegations that Cushing advised Confederate president Jefferson Davis during the Civil War. Cushing eventually left Washington, appointed by President Grant as ambassador to Spain.