In 1895, Older became managing editor of the "San Francisco Bulletin" (later merged with the "San Francisco Call" in 1929). He gained notoriety when he took on the Boss Abe Ruef machine in San Francisco, during the mayoralty of Eugene Schmitz. This led to the corruption trials during the rebuilding of San Francisco following the 1906 earthquake and fire. On September 27, 1907, Older was kidnapped and threatened with murder by private detective Luther Brown, said to be working for the grafters.