Prior to the American Civil War, Webster was a lawyer and Maryland state senator from 1855 to 1859.

In the summer of 1862, he recruited the 7th Maryland Infantry Regiment and served as colonel until he returned to Congress on January 1, 1863.

He graduated from Dickinson College of Carlisle, Pennsylvania in 1847, and afterwards taught school and studied law at the office of Otho Scott of Bel Air, Maryland.

[1][2][3] In 1851, prior to being admitted to the bar, Webster was nominated as a Whig for the office of state's attorney, but lost by a margin of ten votes to William H.

[2] During the American Civil War, Webster was colonel of the 7th Regiment Maryland Volunteer Infantry, serving in 1862 and 1863.

He was elected as a candidate of the American Party (Know Nothing) to the Thirty-sixth Congress, defeating Ramsey McHenry.

[1][3] Webster served in Congress, representing Maryland's 2nd congressional district, starting on March 4, 1859.

[1][2][3] In 1865, he was appointed by President Abraham Lincoln as collector of customs at the Port of Baltimore, serving in that position from July 27, 1865, to April 15, 1869.

Afterwards, he resumed the practice of his profession in Bel Air until he was again appointed collector of customs by President Chester A. Arthur on February 17, 1882.