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Charles Otis could boast of friendships with John D. Rockefeller, comedian Will Rogers, and his distant cousin Amelia Earhart. He knew many United States presidents, from fishing trips with Grover Cleveland to card games with Warren G. Harding. He debated with Teddy Roosevelt on whether the Cleveland News would support TR’s Bull Moose Party. When America entered World War I, Charles was appointed to the War Industries Board, where he worked closely with future president Herbert Hoover. Regardless of being active in Washington, he found the spare time to sell a huge amount of war bonds in Cleveland.

In late 1919, when Prohibition was about to come into effect, Charles and close friend John Sherwin, the banker and future stockholder of the Indians, went on a buying spree. They spent the enormous amount of $30,000 on cases of Old Crow bourbon, whiskey, gin, and champagne. Trucks were hired to load the cases and deliver them to Sherwin’s lavish home in Cleveland Heights. Whenever the rich folks threw a high-powered party, Charles was there with all the booze needed. If you wanted something of importance done, there was only one man in Cleveland to call.

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