While working as a speechwriter for President Bill Clinton from 1998 to 2001, Glastris wrote drafts of more than 200 speeches on a variety of subjects such as education, health care, and the budget. He helped write the State of the Union addresses in 1999 and 2000. In 1999, Glastris traveled with President Clinton to Turkey and Greece and wrote the President's address to Greece. Glastris developed Clinton's "DC Reads this Summer" program. This program "put over 1000 federal employees as volunteer reading tutors in Washington, DC public schools." In 2000, he was also responsible for co-writing the President's address to the Democratic convention in Los Angeles.