Possible Clues:

• "The Michelle ___ Podcast"
• "Dreams From My Father" memoirist
• "Becoming" memoirist
• Time's Person of the Year for 2008 and 2012
• 'Becoming' author Michelle
• Justice Kagan appointer
• President with two Grammys
• First president with a Twitter account
• Illinois senator
• Malia or Sasha