He began the practice of law in Austin, Texas, in 1885. For eight years he was a regent of the University of Texas. He declined appointment as assistant attorney general of Texas in 1892, and an appointment to the state bench in 1896.
Gregory was a delegate to the Democratic National Convention at St. Louis and State delegate at large to the Baltimore convention. He was appointed Special Assistant to the U.S. Attorney General in 1913, in the investigation and proceedings against the New York, New Haven and Hartford Railroad Company.
In 1914, President Woodrow Wilson appointed him Attorney General of the United States, and he held that office until 1919. Gregory was a member of Wilson's Second Industrial Conference in 1919 and 1920.
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