Webb attended Georgetown Law Center from 1972 to 1975, graduating with a Juris Doctor degree.
While at Georgetown, he wrote his first book, Micronesia and U.S. Pacific Strategy.

From 1977 to 1981, Webb worked on the staff of the House Committee on Veterans Affairs.
During this time, he also represented veterans pro-bono.
Webb taught at the Naval Academy and was criticized for a 1979 article published in Washingtonian magazine, titled "Women Can't Fight" (see "2006 Senate campaign" below).
He attended the 1980 Republican National Convention in Detroit and led the Pledge of Allegiance in the opening session.

During the Reagan Administration, Webb served as the nation's first Assistant Secretary of Defense for Reserve Affairs from 1984-87.
In 1987, he served as Secretary of the Navy, becoming the first Naval Academy graduate to serve as the civilian head of the Navy.
As Navy Secretary, Webb pushed the appointment of Alfred M. Gray, Jr. as Commandant of the Marine Corps, hoping that Gray could reshape the Corps into the elite unit it once was.
Webb resigned in 1988 after refusing to agree to reduce the size of the Navy.
Webb had wished to increase the Navy to 600 ships.
As revealed in The Reagan Diaries, President Ronald Reagan wrote on February 22, 1988: "I don't think Navy was sorry to see him go."

In a 1990 New York Times opinion piece, Webb opposed further U.S. military escalation in Saudi Arabia during Operation Desert Shield citing lack of a coherent strategy and consent from the United States Congress.
He also warned against a permanent military presence in the Middle East.
Seven months before the beginning of the 2003 Iraq War, Webb wrote an essay for The Washington Post in which he
questioned whether an overthrow of Saddam would "actually increase our ability to win the war against international terrorism" and pointed out that the measure of military success can be preventing wars as well as fighting them.
He charged, "those who are pushing for a unilateral war in Iraq know full well that there is no exit strategy if we invade."
He concluded, "the Iraqis are a multiethnic people filled with competing factions who in many cases would view a U.S. occupation as infidels invading the cradle of Islam.... In Japan, American occupation forces quickly became 50,000 friends.
In Iraq, they would quickly become 50,000 terrorist targets."

During the 2004 presidential campaign, Webb wrote an op-ed piece for USA Today in which he, as a military veteran, evaluated the candidacies of John Kerry and George W. Bush.
He criticized Kerry for the nature of his opposition to the Vietnam War in the 1970s while affiliated with the Vietnam Veterans Against the War, and accused Bush of using his father's connections to avoid service in Vietnam.
Webb wrote that Bush had "committed the greatest strategic blunder in modern memory" with the 2003 invasion of Iraq.

Webb supported Nebraska Senator Bob Kerrey's campaign for the 1992 Democratic presidential nomination.
In 1994, he endorsed incumbent Democrat Charles Robb for reelection to his Senate seat, over Webb's former Naval Academy classmate Oliver North; like Webb, both Robb and North were decorated Marine veterans of the Vietnam war.
Webb subsequently endorsed Republican George Allen over Robb in 2000, and then ran against Allen himself in 2006.
Webb attended Georgetown Law Center from 1972 to 1975, graduating with a Juris Doctor degree. While at Georgetown, he wrote his first book, Micronesia and U.S. Pacific Strategy.
From 1977 to 1981, Webb worked on the staff of the House Committee on Veterans Affairs. During this time, he also represented veterans pro-bono. Webb taught at the Naval Academy and was criticized for a 1979 article published in Washingtonian magazine, titled "Women Can't Fight" (see "2006 Senate campaign" below). He attended the 1980 Republican National Convention in Detroit and led the Pledge of Allegiance in the opening session.
During the Reagan Administration, Webb served as the nation's first Assistant Secretary of Defense for Reserve Affairs from 1984-87. In 1987, he served as Secretary of the Navy, becoming the first Naval Academy graduate to serve as the civilian head of the Navy. As Navy Secretary, Webb pushed the appointment of Alfred M. Gray, Jr. as Commandant of the Marine Corps, hoping that Gray could reshape the Corps into the elite unit it once was. Webb resigned in 1988 after refusing to agree to reduce the size of the Navy. Webb had wished to increase the Navy to 600 ships. As revealed in The Reagan Diaries, President Ronald Reagan wrote on February 22, 1988: "I don't think Navy was sorry to see him go."
In a 1990 New York Times opinion piece, Webb opposed further U.S. military escalation in Saudi Arabia during Operation Desert Shield citing lack of a coherent strategy and consent from the United States Congress. He also warned against a permanent military presence in the Middle East. Seven months before the beginning of the 2003 Iraq War, Webb wrote an essay for The Washington Post in which he
questioned whether an overthrow of Saddam would "actually increase our ability to win the war against international terrorism" and pointed out that the measure of military success can be preventing wars as well as fighting them. He charged, "those who are pushing for a unilateral war in Iraq know full well that there is no exit strategy if we invade." He concluded, "the Iraqis are a multiethnic people filled with competing factions who in many cases would view a U.S. occupation as infidels invading the cradle of Islam.... In Japan, American occupation forces quickly became 50,000 friends. In Iraq, they would quickly become 50,000 terrorist targets."
During the 2004 presidential campaign, Webb wrote an op-ed piece for USA Today in which he, as a military veteran, evaluated the candidacies of John Kerry and George W. Bush. He criticized Kerry for the nature of his opposition to the Vietnam War in the 1970s while affiliated with the Vietnam Veterans Against the War, and accused Bush of using his father's connections to avoid service in Vietnam. Webb wrote that Bush had "committed the greatest strategic blunder in modern memory" with the 2003 invasion of Iraq.
Webb supported Nebraska Senator Bob Kerrey's campaign for the 1992 Democratic presidential nomination. In 1994, he endorsed incumbent Democrat Charles Robb for reelection to his Senate seat, over Webb's former Naval Academy classmate Oliver North; like Webb, both Robb and North were decorated Marine veterans of the Vietnam war. Webb subsequently endorsed Republican George Allen over Robb in 2000, and then ran against Allen himself in 2006.
Jim Webb