In late 2005, a campaign to draft Webb to run for the Senate in 2006 began on the internet, promoted by netroots activists such as those at the blog Raising Kaine.
On February 7, 2006, he announced that he would seek the Democratic nomination for the 2006 Senate race against incumbent Virginia Senator George Allen.

In the Democratic primary on June 13, 2006, Webb faced longtime businessman and lobbyist Harris Miller.
Webb won with 53.5% of the vote, in a race with low turnout.

On August 11, 2006, an incident occurred in which Allen used the word macaca to refer to S.R. Sidarth, who was filming an event as a "tracker" for the Webb campaign.
A poll the following week showed Webb gaining 10 percentage points.
The race, which at one point looked like a sure win for Allen, became one of the most watched and closest races of the 2006 elections.
Webb's entry into the race and primary victory changed the political landscape.
Political analyst Larry Sabato said in May that "Jim Webb is George Allen's worst nightmare: a war hero and a Reagan appointee who holds moderate positions.... Allen tries to project a Reagan aura, but Webb already has it."

On September 7, 2006, Webb released his first television advertisement, which included footage of a 1985 speech by Ronald Reagan that praised Webb's service as a Marine.
The next day, the Chief of Staff for the Reagan Library wrote Webb's campaign on behalf of former first lady Nancy Reagan, urging them not to air the advertisement saying it was neither fair nor respectful because it gave the impression of an endorsement.
The Webb campaign disagreed, saying, "What Reagan said about Jim Webb, that belongs to Jim Webb, frankly."
The library said they ask all candidates to refrain from using the former president's image but declined to say if they would request the Allen campaign to remove the image of Reagan used on his campaign website.

Five female graduates of the United States Naval Academy held a press conference, decrying Webb's 1979 article, "Women Can't Fight."
The women said Webb's article contributed to an atmosphere of hostility and harassment towards women at the academy.
Webb was later endorsed by nine military women who stated that Webb is a "man of integrity" who "recognizes the crucial role that women have in the military today."

In October 2006, the Allen campaign issued a press release quoting several passages from Webb's novels with sexual content, including graphic references to female anatomy and purported pedophilia, homosexuality and incest, citing a passage in which a Southeast Asian father ritually places the penis of his young son in his mouth.
The press release said that the passages showed a "continued pattern of demeaning women".
Allen's campaign refused to tell a local radio news station, WTOP-FM, whether it in fact had issued a news release on the matter.

In response, Jim Webb explained to The Washington Post, "I actually saw this happen in a slum in Bangkok when I was there as a journalist."
According to an article on Raw Story, the conservative website CNS News cited a case in Nevada in which a Cambodian mother was arrested for a similar act.
According to the CNS article, an office manager for the Cambodian Association of America confirmed it is a cultural norm in Thailand and Cambodia.

On November 9, 2006, after AP and Reuters projected that Webb had won the seat, Allen conceded the election.
Although the margin was narrow – less than half of 1% of the total vote and therefore small enough under Virginia law to allow demanding a recount – Allen stated that he would not challenge the result.
In late 2005, a campaign to draft Webb to run for the Senate in 2006 began on the internet, promoted by netroots activists such as those at the blog Raising Kaine. On February 7, 2006, he announced that he would seek the Democratic nomination for the 2006 Senate race against incumbent Virginia Senator George Allen.
In the Democratic primary on June 13, 2006, Webb faced longtime businessman and lobbyist Harris Miller. Webb won with 53.5% of the vote, in a race with low turnout.
On August 11, 2006, an incident occurred in which Allen used the word macaca to refer to S.R. Sidarth, who was filming an event as a "tracker" for the Webb campaign. A poll the following week showed Webb gaining 10 percentage points. The race, which at one point looked like a sure win for Allen, became one of the most watched and closest races of the 2006 elections. Webb's entry into the race and primary victory changed the political landscape. Political analyst Larry Sabato said in May that "Jim Webb is George Allen's worst nightmare: a war hero and a Reagan appointee who holds moderate positions.... Allen tries to project a Reagan aura, but Webb already has it."
On September 7, 2006, Webb released his first television advertisement, which included footage of a 1985 speech by Ronald Reagan that praised Webb's service as a Marine. The next day, the Chief of Staff for the Reagan Library wrote Webb's campaign on behalf of former first lady Nancy Reagan, urging them not to air the advertisement saying it was neither fair nor respectful because it gave the impression of an endorsement. The Webb campaign disagreed, saying, "What Reagan said about Jim Webb, that belongs to Jim Webb, frankly." The library said they ask all candidates to refrain from using the former president's image but declined to say if they would request the Allen campaign to remove the image of Reagan used on his campaign website.
Five female graduates of the United States Naval Academy held a press conference, decrying Webb's 1979 article, "Women Can't Fight." The women said Webb's article contributed to an atmosphere of hostility and harassment towards women at the academy. Webb was later endorsed by nine military women who stated that Webb is a "man of integrity" who "recognizes the crucial role that women have in the military today."
In October 2006, the Allen campaign issued a press release quoting several passages from Webb's novels with sexual content, including graphic references to female anatomy and purported pedophilia, homosexuality and incest, citing a passage in which a Southeast Asian father ritually places the penis of his young son in his mouth. The press release said that the passages showed a "continued pattern of demeaning women". Allen's campaign refused to tell a local radio news station, WTOP-FM, whether it in fact had issued a news release on the matter.
In response, Jim Webb explained to The Washington Post, "I actually saw this happen in a slum in Bangkok when I was there as a journalist." According to an article on Raw Story, the conservative website CNS News cited a case in Nevada in which a Cambodian mother was arrested for a similar act. According to the CNS article, an office manager for the Cambodian Association of America confirmed it is a cultural norm in Thailand and Cambodia.
On November 9, 2006, after AP and Reuters projected that Webb had won the seat, Allen conceded the election. Although the margin was narrow – less than half of 1% of the total vote and therefore small enough under Virginia law to allow demanding a recount – Allen stated that he would not challenge the result.
Jim Webb