Pitney came to prominence during the 2009 Iranian election protests, where he liveblogged the protest for the Huffington Post by aggregating social media posts from Iranians, including videos and tweets. According to Pitney, over 100,000 comments were left on the popular blog. As a result, Pitney was asked by the Obama administration to be prepared to pose a question from an Iranian at a June 23, 2009 press conference at the White House. In a departure from typical press conference protocol, Pitney was called on second and asked Obama under what conditions the United States would accept the election of Mahmoud Ahmadinejad. While Pitney did not know if he would be called on to ask a question, and President Obama did not know what question would be asked, a number of critics, including members of the White House press corps charged that the question was an example of improper collusion between the White House and a journalist. One of the most prominent critics was Dana Milbank of the Washington Post. Pitney and Milbank engaged in a heated and personal debate on the CNN program Reliable Sources about the question, and according to Pitney, Milbank whispered to Pitney during a commercial break "You're such a dick". This incident spawned the Twitter hashtag #Dickwhisperer.
Pitney left The Huffington Post in 2012 to travel the world and blog about his experience with his wife Karina Newton, former new media director for House Minority LeaderNancy Pelosi. In 2013, Pitney returned to The Huffington Post as head of product. In 2017, he joined NowThis as political director.
^Huffington, Arianna (23 June 2009). "Media Playground: Obama Calls on HuffPost, Michael Calderone Pouts, Ben Smith Calls Us Names, Dana Milbank Gets His Facts All Wrong". Huffington Post. Missing or empty |url= (help)