Chester Ashley (June 1, 1790 – April 29, 1848) was an American politician who represented Arkansas in the U.S. Senate from 1844 until his death.
Ashley was born in Amherst, Massachusetts in 1790; while a child he moved with his parents to Hudson, New York. He was a graduate, with honors, of Williams College; following this, he took a course in law in Litchfield, Connecticut. Ashley moved west upon completion of his education, going first to Illinois, and thence to Missouri. In 1820 he arrived in Little Rock, Arkansas, soon becoming one of the best and most prominent lawyers in the Arkansas Territory; for a time, his partner in practice was Robert Crittenden. Together, Ashley and Crittenden founded Rose Law Firm.
For some twenty years Ashley's practice was the largest in the state, and he became a wealthy man. This led him to try his hand at politics; in 1844 he canvassed the state campaigning for James K. Polk for president; the Democrats were victorious, and Ashley was elected by the state legislature to fill a vacancy in the Senate. Soon after entering, he was made the Chairman of the Senate Judiciary Committee; in 1846, he was reelected to the Senate. Two years later he was taken suddenly ill in the Senate Chamber and died not long after.
Chester Ashley is the namesake of Ashley County, Arkansas.