John Dickson , 37 , a high school government teacher from Brewster , Mass . , and his brother-in-law Jim Murray , 34 , an investment banker from Bedford , N.Y. , flew into Chicago on New Year 's Day to join a third friend , only to get up with the sun to drive into Iowa for a day of events with Mr. Obama , Senator Hillary Rodham Clinton , Mitt Romney , Mr. Obama again -- and then a powwow to regroup .