Simon has been with NPR for over four decades, beginning in 1977 as Chicago bureau chief, and his career encompasses other types of media as well. He has hosted the Saturday edition of Weekend Edition since its inception in 1985, with the exception of a brief period in 1992 and 1993 when Alex Chadwick hosted the show. His books include My Cubs: A Love Story ; Home and Away: Memoir of a Fan ; Jackie Robinson and the Integration of Baseball ; Baby, We Were Meant for Each Other: In Praise of Adoption, about his experiences adopting two daughters; and the novels Pretty Birds and Windy City: A Novel of Politics. He has also hosted many television series and specials, including PBS's Need to Know in 2011–13. He guest-hosted BBC World News America, filling in for Matt Frei, and anchored NBC's Weekend Today in 1992–93.
Controversies
After September 11, 2001, Simon spoke and wrote in support of the "war on terror", publishing an op-ed in the October 11, 2001, Wall Street Journal titled "Even Pacifists Must Support This War." He questioned nonviolence at greater length in the Quaker publication Friends Journal in December 2001, provoking many angry letters, to which he replied in the May 2003 issue. On November 15, 2014, at the beginning of an interview for Weekend Edition Saturday, Bill Cosby and his wife Camille declined to respond to the accusations of sexual assault against Cosby when Simon gave them the opportunity. As narrated by Simon in the interview, Cosby only shook his head no. The rest of the interview focused on the couple's loan of their 62-piece African art collection for an exhibition in Washington, D.C. On December 15, 2018, Simon opened a story on the death of Jakelin Caal by saying, "I do not doubt that U.S. Customs and Border Protection agents did all they could to try to save the life of Jakelin Caal Maquin, a 7-year-old girl from Guatemala, who died in the custody of the United States." Journalist Jon Schwarz from The Intercept criticized Simon on Twitter.
Simon met French documentary filmmaker Caroline Richard during an NPR interview in 2000. They married on September 10, 2000, in a mixed-faith service in Ridgefield, Connecticut, at the home of fashion designer Alexander Julian. They have two daughters, both adopted as babies from China: Elise, in 2004, and Lina, in 2007. They consider themselves a Jewish family. In 2006 Simon and his wife were contacted by police as part of the Alexander Litvinenko poisoning investigation. The family was staying at a hotel near the restaurant at the center of the poisoning incident, and had twice bought food there for their daughter Elise. The health of the family was not affected. In July 2013, in a groundbreaking use of social media, Simon began tweeting his emotions and conversations with his mother during her last days of life, which she spent in a hospital intensive-care unit. "I just realized: she once had to let me go into the big wide world. Now I have to let her go the same way", read one tweet. In March 2015, he published a memoir about her titled Unforgettable: A Son, a Mother, and the Lessons of a Lifetime. He is the nephew of Jack Brickhouse.