After selling the Baltimore and Washington City Papers for $4 million, Smith founded New York Press in 1989.
In 2002 Avalon Equity Partners, publisher of a chain of gay alternative weeklies including the New York Blade and the Washington Blade, purchased the paper from Smith, although they continued to publish his 10,000+ word weekly column, MUGGER.
A libertarian Republican[1] (he is an advocate of the legalization of prostitution, gambling, same-sex marriage, and currently illegal drugs), Smith is a contributor to The Wall Street Journal's editorial page, a position that he has held since 1999; he also writes for the paper's "Taste" section.
Other publications Smith has written for include Baltimore's Press Box, The New York Sun, and Jewish World Review.
In March 2008, Smith founded the website Splice Today, which features a variety of authors including Crispin Sartwell, William Bryk, and Mark Judge.