At just 27, this this Winchester, Massachusetts born, die-hard Democrat became the second youngest ever head presidential speechwriter ever on a salary of $172,200 per year (£102,000). Obama’s “mind reader” between 2009 and 2013 likes to play the piano and the Red Sox. With over 35,000 followers on Twitter, Jon Favreau has featured on both Time’s “100 most influential” list and Vanity Fair’s “Next Establishment” list and is now one of the founding partners of Fenway Strategies, a consulting firm. He is afraid of flying and had to apologise for grabbing the breast of a cardboard cutout of Hillary Clinton in 2008. Laughing it off, Clinton’s aides commented: “Senator Clinton is pleased to learn of Jon’s obvious interest in the State Department”.