[4] In addition, he continued his affiliation with Columbia after receiving his degree, teaching equity and serving as a member and chairman of the law school's Board of Visitors.

[5] Woolsey was nominated by President Calvin Coolidge to the United States District Court for the Southern District of New York, February 28, 1929, but the United States Senate did not vote on the nomination and it expired on March 3, 1929, with the end of Coolidge's presidency.

[3] Woolsey was renominated by President Herbert Hoover on April 18, 1929, to a new seat in the Southern District which had been authorized by 45 Stat.

[8] This decision, which came about in a test case engineered by Bennett Cerf of Random House, was affirmed by a 2–1 vote of the United States Court of Appeals for the Second Circuit in an opinion by Judge Augustus Noble Hand.

His holding was on the technical grounds that the order was signed by the President, not the Secretary of the Treasury as required,[11] and forced the Roosevelt administration to issue a new order signed by the Secretary of the Treasury, Henry Morgenthau Jr. Judge Woolsey assumed senior status on December 31, 1943, due to disability.