James Dolan (computer security expert)

Early Life

James S. Dolan was born on July 20, 1981, and grew up in Chester, New York, where he was raised alongside four sisters. He attended the Tuxedo Park School and was considered gifted from an early age. He later relocated to Brooklyn, though he also returned to Chester at various points in his life.

Military Service

From 1999 to 2006, Dolan served with the United States Marines, completing two deployments during the Iraq War as a data network specialist. In 2003, he served with III Marine Expeditionary Force during the initial invasion of Iraq. His second deployment, from September 2004 to March 2005, placed him with the 4th Civil Affairs Group in Fallujah — one of the most contested areas of the conflict at that time. Dolan was present during Operation Phantom Fury, part of the Second Battle of Fallujah. According to Trevor Timm of the Freedom of the Press Foundation, Dolan frequently cited the impact of his Iraq service as a motivating factor in his subsequent cybersecurity work, particularly his goal of making metadata "transparent and accountable."

Career

Following his military service, Dolan worked in computer security at a large IT company. In 2012, as a side project, he joined Aaron Swartz and Kevin Poulsen in developing SecureDrop — initially called DeadDrop — an open-source platform designed to allow sources to anonymously submit materials to journalists. Dolan served as the lead maintainer of the project.

After Aaron Swartz's death in 2013, Dolan and Poulsen transferred SecureDrop to the Freedom of the Press Foundation to ensure its continued development and broader adoption. As the Foundation's first employee, Dolan conducted outreach and assisted in installations of the platform at numerous prominent news organizations, including The New Yorker, ProPublica, The Washington Post, The New York Times, The Wall Street Journal, and VICE News, among dozens of others.

In 2015, Dolan moved to San Diego, California, to take on the role of head of security at Classy, an online fundraising platform designed for nonprofit organizations — a position he held at the time of his death.

Death

Dolan was found dead in a Brooklyn hotel on December 27, 2017, at the age of 36. Former colleagues have speculated that he died by suicide. He had reportedly developed PTSD stemming from his time in the Marines. Dolan was the second member of the SecureDrop development team to die by suicide, following Aaron Swartz.

Legacy

Following his death, fellow Marines established the James Dolan Memorial Fund through GoFundMe, with the aim of making annual donations to designated nonprofit foundations and projects in his name. SecureDrop, the platform Dolan helped build and sustain, remains one of the most widely adopted secure whistleblower submission systems in journalism.