In 1989, Staines published In the Grip of the Sandinistas: Human Rights in Nicaragua 1979–1989, under the auspices of the International Society for Human Rights (of which he was UK secretary-general), analysing the Sandinistas in Nicaragua from 1979 to 1989. He was then the editor of Human Rights Briefing.

Staines is a libertarian who described in a 2000 publication, how he became a libertarian in 1980 after reading Karl Popper’s The Open Society and its Enemies. He joined the Young Conservatives whilst at Humberside College of Higher Education, “because they were the only people around who were anti-Socialist or at least anti-Soviet”. Having joined the Federation of Conservative Students, he described his politics as “Thatcher on drugs”. He relates that at college he was a “right-wing pain in the butt who was more interested in student politics than essays”, who went on “to work in the various right-wing pressure groups and think tanks that proliferated in the late eighties”. He once said, “I never wore a ‘Hang Mandela’ badge, but I hung out with people who did”.

In 2002, Staines was banned from driving for 12 months for drink driving. When he was convicted of the same offence six years later, he was asked in court by District Judge Timothy Stone whether he had an alcohol problem and replied: “Possibly.” He was banned from driving for three years, as well as being given an 18-month supervision order and wearing an electronic tag for three months.

In 2006, Staines along with Jag Singh co-founded MessageSpace, a digital advertising agency which operates an advertising network representing dozens of leading political websites. In 2012 it advised the successful Boris Johnson London mayoral campaign. Private Eye reported in June 2012 that MessageSpace was advising the Russian Embassy in London on using social media.