In 1984, he ran again for the U.S. Senate. Tower decided to retire but Krueger lost in the Democratic primary, caught in the middle between the more liberal State Senator Lloyd Doggett and the more conservative U.S. Representative Kent Hance. In 2010, Krueger's campaign was named by the "Houston Chronicle" as the ninth-worst in Texas' modern political history, saying: "Caught in the middle, Krueger seemed like a bland centrist facing a fiery liberal and a folksy conservative. He ended up finishing third, out of the runoff and out of luck." From 1985 to 1989, he also wrote a regular column on a broad range of public affairs issues, which was carried in newspapers in San Antonio, Dallas, Houston, and Corpus Christi, Texas.