Until June 11, 2017 Segal authored the bi-weekly "The Haggler" column in the Sunday edition of The New York Times, in which he printed and attempted to resolve reader-submitted letters about plights in customer service. His column covered companies such as Sears,Apple,Samsung, and many others. It was generally written in a semi-third person style, in which he referred to himself as "The Haggler" rather than "I". His interventions were generally successful.
Segal's December 2010 story about a Brooklyn-based online eyeglass seller, Vitaly Borker, who manipulated his site's Google search ranking through negative publicity received attention from the media and prompted Google to alter its algorithms.
Before joining the New York Times in 2008, Segal worked for 14 years at The Washington Post, four of them spent as the paper's pop music critic and four others as the paper's Style section correspondent in New York City. At The Post, Segal wrote a profile about a British man who sued Wilco for using sounds he'd recorded in the band's album Yankee Hotel Foxtrot. This profile was later published in Da Capo Best Music Writing 2005.
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