Scott was born and educated in Virginia; after brief attendance at the College of William and Mary and study in a law office, he attained admission to the bar. Scott practiced law briefly, and served in the Virginia Militia during the Chesapeake–Leopard Affair. In 1808, Scott was commissioned as a captain in the Light Artillery. He rose to prominence during the War of 1812, and attained promotion to brigadier general. Scott remained in the Army after the war, served in several command positions, and carried out high level staff tasks, including frequent updates to the Army's field regulations. After missing out on appointment as the Army's commanding general in 1828, he received the appointment in 1841; he served in this post until his retirement in 1861, shortly after the start of the American Civil War.
At the start of the Civil War, Scott took steps to defend Washington, DC and ensure the successful inauguration of Abraham Lincoln. Though too old and infirm to take the field, Scott served as Lincoln's principal military adviser at the start of the war, and conceived of the Anaconda Plan; though dismissed by critics who regarded the plan's extended and prolonged blockade of southern ports as too passive, Scott's idea was incorporated into the overall Union strategy which brought about the defeat of the Confederacy.
Winfield Scott was born on June 13, 1786, to William Scott (1747–1791), a farmer and veteran of the American Revolution who served as an officer in the Dinwiddie County militia, and Ann Mason (1748–1803). At the time, the Scott family resided at Laurel Branch, the family plantation in Dinwiddie County, near Petersburg, Virginia. Ann Mason Scott was the daughter of Daniel Mason and Elizabeth Winfield, and it was Ann's mother's maiden name that William and Ann Scott selected for their son. He was educated by tutors and in the local schools; his father died when Scott was six, and his mother when Scott was seventeen. In 1805, Scott began attendance at the College of William and Mary, but he soon left in order to study law in the office of attorney David Robinson, where his contemporaries included Thomas Ruffin. By 1807, Scott had attained admission to the bar, and he made a brief attempt to practice law. He also gained his initial military experience as a corporal of cavalry in the Virginiamilitia near Petersburg in 1807, during the response to the Chesapeake–Leopard Affair. (According to biographer John Eisenhower's account, Scott served with the militia without having been officially mustered in.) While serving near Lynn Haven Bay, Scott led a detachment that captured two midshipmen and six sailors from the British fleet, who had attempted to land and purchase provisions. Virginia authorities did not approve of this action, fearing it might spark a wider conflict; they soon ordered the release of the prisoners, who rejoined the crew of their ship.
In October 1807, Scott traveled to South Carolina, intending to establish a law practice. He soon discovered that South Carolina required a one-year residence before granting law licenses, and requested a waiver of the residence period from the state legislature, which was denied. He briefly resided in Charleston, where he intended to practice without appearing in court until he had established residence. Abandoning this idea, he briefly practiced again in Petersburg, but the continued threat of war with Britain coupled with his militia experience led Scott to decide upon an Army career, and he decided to apply for a commission.