Webb was born to a military family in Corona, California. At the age of 15, Webb began writing editorials for his high school newspaper while living in suburban Indianapolis. At the height of the protests against the Vietnam War, he created his first controversy when he criticized the use of a female drill team to rally students for the war effort.
Webb later attended journalism school at Northern Kentucky University, where he was on staff at the student newspaper, The Northerner, but dropped out. He started his professional career in journalism by first working for the Kentucky Post and then as a statehouse correspondent for the Cleveland Plain Dealer. Webb investigated government and private sector corruption, a passion that would highlight his entire career as a journalist.
In 1988, Webb joined the San Jose Mercury News as a staff writer. He helped expose freeway retrofitting problems in the 1989 Loma Prieta earthquake and wrote stories about computer software problems at the California DMV.
In August of 1996, the San Jose Mercury News published Webb's "Dark Alliance", a 20,000 word, three-part investigative series which alleged that Nicaraguan drug traffickers had sold and distributed crack cocaine in Los Angeles during the 1980s, and that drug profits were used to fund the CIA-supported Nicaraguan Contras. Webb never asserted that the CIA directly aiding drug dealers to raise money for the Contras, but he did imply that the CIA were aware of the transactions (Webb's 1999 book, Dark Alliance, substantiated these allegations with copious references).
"Dark Alliance" received national attention. At the height of the interest, the web version of it on San Jose Mercury News website received 1.3 million hits a day. According to the Columbia Journalism Review, the series became "the most talked-about piece of journalism in 1996 and arguably the most famous -- some would say infamous -- set of articles of the decade."
Webb supported his story with documents obtained through the Freedom of Information Act, including a 450-page declassified version of an October, 1998 report by CIA Inspector General Frederick Hitz. According to Webb and his supporters, the evidence demonstrates that White House officials, including Oliver North, knew about and supported using money from drug trafficking to fund the contras, and these officials neglected to pass any information along to the DEA. The 1988 report from the Senate Subcommittee on Narcotics, Terrorism and International Operations commented that there were "serious questions as to whether or not US officials involved in Central America failed to address the drug issue for fear of jeopardizing the war effort against Nicaragua."
Almost immediately, denials began to emerge of the assertions Webb made in "Dark Alliance". Subsequent reports in the Washington Post (Oct 4, 1996), Los Angeles Times, New York Times (Oct 21, 1996) tried to debunk the link between the Contras and the crack epidemic. However, as Richard Thieme observed, the major news outlets focused primarily on attacking him or criticizing irrelevant parts of the story itself, leaving Webb's thesis virtually intact. Because of these attacks, Webb created a web site that contained primary documents, transcripts, and audio interviews so that people could examine the evidence for themselves.
However, under mounting pressure, San Jose Mercury News executive editor Jerry Ceppos published a retraction on May 11, 1997, claiming the Dark Alliance series fell short of his standards. Webb was reassigned to a suburban bureau one hundred fifty miles from his home. Because of the long commute, Webb quit the paper in December, 1997, but by then his marriage had fallen apart and his career had been destroyed.
Facing increasing public scrutiny from the fallout after Webb's Dark Alliance series, the CIA conducted its own internal investigations. Investigative journalist Robert Parry credits Webb for being responsible for the following government investigations which revealed how the Reagan-Bush administration had conducted the contra war:
On Jan. 29, 1998, CIA Inspector General Frederick Hitz published Volume One of his internal investigation. This was the first of two CIA reports that eventually substantiated many of Webb's claims about cocaine smugglers, the Nicaraguan contra movement, and their ability to freely operate without the threat of law enforcement.
On March 16, 1998, CIA I.G. Hitz admitted that the CIA had maintained relationships with companies and individuals the CIA knew were involved in the drug business. Hitz told the House Permanent Select Committee on Intelligence that, "...there are instances where CIA did not, in an expeditious or consistent fashion, cut off relationships with individuals supporting the contra program who were alleged to have engaged in drug-trafficking activity or take action to resolve the allegations." (Pincus, Washington Post, Mar. 17, 1998) Senator John Kerry had reached similar conclusions in 1997, but his findings as well as the surprising admissions from the CIA were generally ignored by the media.
On May 7, 1998, Rep. Maxine Waters, revealed a letter between the CIA and the Justice Department. This letter had freed the CIA from legally reporting drug smuggling by CIA assets, a provision that covered the Nicaraguan contras and the Afghan rebels.
On July 23, 1998, the Justice Department released a report by its Inspector General, Michael Bromwich. The Bromwich report claimed that the Reagan-Bush administration was aware of cocaine traffickers in the contra movement and did nothing to stop the criminal activity. The report also revealed a pattern of discarded leads and witnesses, sabotaged investigations, instances of the CIA working with drug traffickers, and the discouragement of DEA investigations into contra-cocaine shipments. The CIA's refusal to share information about contra drug trafficking with law-enforcement agencies was also documented. The Bromwich report corroborated Webb's investigation into Norwin Meneses, a Nicaraguan drug smuggler.
On October 8, 1998, CIA I.G. Hitz published Volume Two of his internal investigation. The report described how the Reagan-Bush administration had protected more than 50 contras and other drug traffickers, and by so doing, deliberately thwarted federal investigations into drug crimes. Hitz published evidence that drug trafficking and money laundering had made its way into Reagan's National Security Council where Oliver North oversaw the operations of the contras. According to the report, the contra war took precedence over law enforcement. To that end, the internal investigation revealed that the CIA routinely withheld evidence of contra crimes from the Justice Department, Congress and even the analytical division of the CIA itself. Further, the report confirmed Webb's claims regarding the origins and the relationship of contra fundraising and drug trafficking. More importantly, the internal CIA report documented a cover-up of evidence which had led to false intelligence assessments. According to Robert Parry, these erroneous assessments were passed on to Congress and eventually, major media outlets, which used the false datasets to criticize the accuracy of Webb's Dark Alliance expose.
Dark Alliance: the book
In 1999, Webb published the controversial Dark Alliance series in its full, uncensored form, complete with extensive source citations. The book entitled, Dark Alliance: The CIA, the Contras, and the Crack Cocaine Explosion, received favorable reviews.
Although moved to investigate itself concerning Webb's premise of a "Dark Alliance" between the Contras and elements of the CIA, Inspector General Hitz found "no direct or indirect" links between the CIA and the cocaine traffickers.
The book includes an account of a meeting between a pilot (who was making drug/arms runs between San Francisco and Costa Rica) with two Contra leaders who were also partners with the San Francisco-based Contra/drug smuggler Norwin Meneses. According to eyewitnesses, Ivan Gomez, identified by one of the Contras as a CIA agent, was allegedly present at the drug transactions. The pilot told Hitz that Gomez said he was there to "ensure that the profits from the cocaine went to the Contras and not into someone's pocket."
According to Webb, Judd Iverson, a San Francisco defense attorney who represented former Contra Julio Zavala, discovered compelling evidence demonstrating that "agents of the U.S. government were intricately involved in sanctioning cocaine trafficing to raise funds for Contra revolutionary activity". (Dark Alliance, pp. 92-95) Soon after, members of the Justice Department persuaded U.S. District Court Judge Robert Peckham to seal the documents in the case.
After leaving San Jose Mercury News Webb went to work for the California Assembly Speaker's Office of Member Services and served as a consultant to the California State legislature Task Force on Government Oversight. As a member of the Joint Legislative Audit Committee, Webb investigated charges that Oracle Corporation received a no-bid contract award of $95 million in 2001 from former California Governor Gray Davis. Webb was hired by the Sacramento News and Review, after being laid off in 2003 with the rest of the former Speaker's staff as part of a house-cleaning when the new House speaker took over.
On December 10, 2004, he was found dead from gunshot wounds to the head. While acknowledging two sets of wounds was unusual, coroner Robert Lyons determined it was suicide. It subsequently became known that Webb had been suffering from clinical depression for many years.
(1997) Media Hero Award, from the 2nd Annual Media & Democracy Congress.
(1996) Journalist of the Year, Bay Area Society of Professional Journalists.
(1994) H.L. Mencken Award, by The Free Press Association for the series in the San Jose Mercury News on abuses in the state of California's drug asset forfeiture program.
(1990) Pulitzer Prize, in General News Reporting, awarded to the Staff of the San Jose Mercury News for its detailed coverage of the October 17, 1989, Bay Area earthquake and its aftermath. 
Quote: "If we had met five years ago, you wouldn't have found a more staunch defender of the newspaper industry than me ... I was winning awards, getting raises, lecturing college classes, appearing on TV shows, and judging journalism contests. So how could I possibly agree with people like Noam Chomsky and Ben Bagdikian, who were claiming the system didn't work, that it was steered by powerful special interests and corporations, and existed to protect the power elite? And then I wrote some stories that made me realize how sadly misplaced my bliss had been. The reason I'd enjoyed such smooth sailing for so long hadn't been, as I'd assumed, because I was careful and diligent and good at my job ... The truth was that, in all those years, I hadn't written anything important enough to suppress."
Celerino III Castillo & Dave Harmon (1994). Powderburns: Cocaine, Contras & the Drug War. Sundial. ISBN 0889625786 (paperback) ISBN 0809548550 (hardcover; Borgo Pr; 3rd ed.; 1995).
Note: Hitz, then CIA Inspector General, was the person who first mentioned the secret agreement between CIA and the Department of Justice, in March 1988, when testifying before the House Intelligence Committee.
Robert Parry (1999). Lost History: Contras, Cocaine, the Press & "Project Truth". Media Consortium. ISBN 1893517004.
Peter Dale Scott & Jonathan Marshall (1991). Cocaine Politics: Drugs, Armies, and the CIA in Central America. University of California Press. ISBN 0520214498 (paperback, 1998 reprint), ISBN 0520073126 (hardcover, 1991), ISBN 0520077814 (paperback, 1992 reprint).
Webb, Gary (1998). Dark Alliance: The CIA, the Contras, and the Crack Cocaine Explosion. Seven Stories Press. ISBN 1888363681 (hardcover, 1998), ISBN 1888363932 (paperback, 1999).