In the same 1995 memo from Caputo, she suggested that the Clinton’s host a big party at the White House to celebrate their anniversary -- even doing an interview with Walters to publicize it.
The timing would allow the Clinton’s to sit down for an interview without appearing "too political," Caputo said. "This might be a nice time peg to have the President and Hillary do a special joint television interview with Barbara Walters. A Barbara Walters interview would attract an important audience of women and senior. If we did an interview around the anniversary time peg, it would not appear too political."
In a July 1999 memo, Clinton’s close adviser Mandy Grunwald offered the first lady "style pointers" for an upcoming public appearance, including recommending she "be careful to ‘be real’” and “look for opportunities for humor.” She also warned her to prepare for a few specific questions, including "have you ever used drugs?"
"Don't be defensive. Look like you want the questions: The press is obviously watching to see if they can make you uncomfortable or testy. Even on the annoying questions, give relaxed answers," Grunwald suggested. "Keep your tone conversational… Don't let their [the large audience’s] presence force you to raise your voice or turn your statement into a speech. It's important that your tone stay informal and relaxed and therefore not political.
“Don't use the Administrations [sic] record as your own: You've spent a lot of years saying, ‘My husband did X.' This trip is about you. And you are not an incumbent. Look for opportunities for humor. It's important that people see more sides of you, and they often see you only in very stern situations."
In Caputo’s 1995 memo, she lamented that there was rarely any "historical context" in articles about Hillary, which could put her activities as first lady into perspective and make her seem "less extreme" as she tried to push for universal healthcare.
For that, she suggested enlisting the help of Eleanor Roosevelt: "Eleanor Roosevelt's Birthday -- Eleanor Roosevelt's birthday is in October and it would be wonderful for Hillary to celebrate the birthday with a day of events at the White House. I think it is beneficial to Hillary to do historical events every month or every 6 weeks. These events will help place a context around her and what she is doing as First Lady. We should look for historical events to celebrate that will help put Hillary into an historical context. So often there is no historical context in stories written about Hillary. If we are able to place her in situations which celebrate historical events, it may help to round out her image and make what she is doing seem less extreme or different in the eyes of the media."