Cowles then supported the Guthrie's demolition in 2006 for the expansion of the Minneapolis Sculpture Garden next door to the Walker Art Center.

Cowles had a progressive political viewpoint, publishing editorials supporting the civil rights movement and liberal causes.

[6] In 1965, Cowles acquired half-interest in Harper's magazine which during his fifteen-year tenure lost readers and nearly US$2 million.

His handling of Dwight's termination led to his removal as editor in 1983, although his family retained a controlling financial interest in the newspaper.

[6] In a 2006 essay written at the University of Minnesota Hubert H. Humphrey Institute of Public Affairs, Cowles wrote, "The nonprofit sector must reform itself, most notably by initiating some minimum federal standards of behavior and by limiting the lifespan of private foundations to 25 or 30 years so that emphasis is on accomplishment, not process and perpetuation.