- Challenged Sammy Sosa to a post-game drug test in 2002 after Sosa claimed he would take one if someone offered it to him. The slugger was not amused by Reilly's offer and threatened the writer.
- Founded the Nothing but Nets charity, which supplies mosquito nets to children in malaria-stricken African communities.
- Voted Sportswriter of the Year 11 times while at Sports Illustrated.
- Cowrote the screenplay for Leatherheads, a comedy about mid-1920s pro football that starred George Clooney and Renee Zellweger.
- Showed off his 7-handicap golf ability by winning a father-son golf tournament with his son at Denver Country Club.
- Honored with the prestigious 2009 Damon Runyan Award for Outstanding Contributions to Journalism.