The Times-Star strongly supported political boss George B. Cox, to the embarrassment of Charles Phelps Taft's half-brother, progressive reformer and future President William Howard Taft.

On November 23, 1895, the Times-Star ran an editorial proposing a contest to choose a flag for the City of Cincinnati, offering a $50 prize.

[3][4] On January 24, 1896, the commission awarded the $50 to influential illustrator Emil Rothengatter for the design that is in use today.

A bidding war ensued when Enquirer employees pooled their assets in order to make a counter offer.

On August 3, 1958, the Times-Star was sold to Scripps-Howard Newspapers, owners of The Cincinnati Post, which by then had also purchased the Enquirer.