Stressing aggressive news coverage, Robert Wills developed the Milwaukee Sentinel as the leading local newspaper in the city in the 1960s. He started his career in Milwaukee as a reporter in 1951, but spent most of his career as editor of the Sentinel from 1962 to 1991. Wills later became President and Vice Chairman of Journal Sentinel Inc. and Publisher of the Milwaukee Journal.
He retired in 1993, having served the Milwaukee newspapers for 42 years.
Wills has always been a champion in promoting freedom of the press. He was a founder of the Wisconsin Freedom of Information Council and served as its first president from 1979 to 1986.
He served as national president of the Society of Professional Journalists from 1986 to 1987. During his presidency, SPJ launched Project Watchdog, a First Amendment public education program, which he championed around the country. Wills served on the Sigma Delta Chi Foundation board of directors from 1993 to 1996. He was president of the Milwaukee SPJ Chapter, which in 1973 gave him its Newsman of the Year Award. The chapter later renamed its Freedom of Information award the Robert H. Wills Freedom of Information Award.
Wills is also a past president of both the Wisconsin Newspaper Association and Wisconsin Associated Press. A winner of the WNA Distinguished Service Award, he has helped choose Pulitzer Prize winners over the years. He also has served on the Media-Law Relations Committee of the Wisconsin Bar.