In 1840 and 1846, he published a digest of the decisions of the Supreme Court of Alabama, and in 1849, he was elected Chairman of the State Convention called for the purpose of promoting internal improvements.

A delegate to the 1852 Democratic National Convention at Baltimore, Maryland, Phillips gave a speech in support of Franklin Pierce who received the nomination.

There he was closely associated with Stephen A. Douglas and largely responsible for the final language of the portion of the notorious Kansas-Nebraska Act that specified that the Missouri Compromise of 1820 be "inoperative and void" for Kansas and Nebraska, but not technically repealed.

Fortunately, he had previously secured the friendship of Edwin M. Stanton, later Secretary of War, who, aided by other prominent Union leaders, arranged for their parole and transportation to the South.

After a harrowing trip and a supposed delivery of information to President Jefferson Davis and other Confederate leaders in Richmond, Virginia, they passed on to Savannah, Georgia and ultimately to the expected safety of New Orleans, Louisiana.

Soon his wife, Eugenia, who laughed at and mocked a Union soldier's funeral cortege, was arrested again and treated as a repeat offender,[3] sent to a prison on Ship Island for three months.

Upon her release in October 1862, again securing permission to leave Union-held territory, the family purchased a small house at LaGrange, Georgia where they lived for the remainder of the war.