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His political blogs are among the most widely read on the Web. Sullivan is considered and credited by many as a pioneer in political weblog journalism, as he is one of very few prominent political journalists in the United States who started his own personal blog, a grass roots online publication in the early days of blog technology. After producing his blog for a year at Time Magazine, on 1 February 2007 Sullivan moved to the Atlantic Monthly, where his blog received approximately 40 million page views in the first year.
Sullivan is known for his unusual personal-political identity (HIV-positive, gay, self-described conservative often at odds with other conservatives, practicing Roman Catholic, and a non-U.S. citizen who focuses on American political life). He has said that he would like to become a US citizen but is barred because of his HIV-positive status.
His political philosophy includes a broad range of traditional conservative positions: He favors a flat tax, limited government, privatization of social security, and a strong military, and he opposes welfare state programs such as socialized medicine.
A self-identified member of the gay “bear community,” in 2003 Sullivan wrote a whimsical and oft-cited Salon essay on the subject.
In 2006 Sullivan expressed interest (at the suggestion of a reader) in creating a new “award” honoring Nancy Grace. The Nancy Grace Award would be bestowed on those evincing “lack of grace and empathy,” a “misplaced self-regard,” “unflappable self-assurance that [the nominee’s] outrage represents the true moral high ground on any issue,” and a “nauseating level of absolutist self-righteousness on the part of the Nominee.” Kaus suggested that this description perfectly fit Sullivan himself; Sullivan hasn’t mentioned the Grace Award since.
In May 2001, Village Voice columnist Michael Musto said that Sullivan had anonymously posted advertisements for bareback sex (anal sex without a condom) on America Online and the now-defunct website barebackcity.com. Subsequently, the American journalist and activist Michelangelo Signorile wrote about the scandal in a front-page article in the New York gay magazine LGNY, igniting a storm of controversy. Later, in a defiant blog post titled Sexual McCarthyism: An article no-one should have to write, Sullivan confirmed the allegations while arguing that the matters covered by the controversy were private and should not have been put into the public domain by his critics.