[4] He became co-owner with his brother John of the Cowles Media Company (established in 1935), and in 1937 became co-founder, co-publisher, and editor of Look magazine.

In the 1940 Republican Party presidential primaries, Cowles and his brother supported Wendell Willkie in their newspapers and magazines.

[2] In the fall of 1942 Cowles and Barnes accompanied Willkie, who was serving as special representative of President Roosevelt, in his international tour (North Africa - Beirut - Jerusalem - Soviet Union - Siberia - China).

[8] In his 1985 memoir Mike Looks Back Cowles claimed Willkie had asked him to cover for him during an assignation with Madame Chiang.

The two had absented themselves from a banquet, Cowles said, leaving him to confront an angry generalissimo and three of his gun-wielding bodyguards—later inflated to 'sixty' in Washington gossip circles—who searched the guesthouse and found nothing.

[9] For a time, Cowles owned the infamous "petrified man" the Cardiff Giant, which he bought to adorn his basement rumpus room as a coffee table and conversation piece.