Douglas Caddy was educated at Georgetown University School of Foreign Service (B.S. degree) and New York University School of Law (J.D. degree).

While a student he developed right-wing opinions and as a teenager became a strong supporter of Barry Goldwater.

In September, 1960, Doug and William F. Buckley established the far right group, Young Americans for Freedom (YAF).

After graduating from New York University School of Law in 1966 Doug went to work for General Foods Corporation.

Doug left General Foods and joined the Washington Law firm of Gall, Lane, Powell and Kilcullen. In 1970 E. Howard Hunt became a client of the company. When Charles Colson invited Hunt to join the White House staff in 1971, Doug provided him with a character reference.

On the 17th June, 1972, Frank Sturgis, Virgilio Gonzalez, Eugenio Martinez, Bernard L. Barker and James W. McCord were arrested while in the Democratic Party headquarters in Watergate. Doug and Joseph Rafferty arranged to represent Sturgis, Gonzalez, Martinez, Barker, McCord, Hunt and Liddy.

On 10th July, 1972, Earl J. Silbert filed a “motion to Compel Testimony of Grand Jury Witness Michael Douglas Caddy. At issue were 38 key questions that Doug refused to answer. According to Doug, these “38 questions was to attempt through my lips as their defense attorney to implicate and incriminate Hunt and Liddy in the break-in.” On 13th July, Doug once again refused to answer these questions and therefore John J. Sirica  sent him to prison.

In recent years Douglas Caddy has moved to the left. He describes himself as a “progressive-liberal” who supported Al Gore for President in 2000 and Howard Dean for President in 2004 and belongs to People for the American Way (ACLU).