During the depression era, the C&O started looking for a new advertising slogan to show how smooth and relaxing a railroad ride could be. At about that time, the company's Vice President, Lionel C. Probert, noticed a picture of a sweet little kitten sleeping on a pillow in the New York's Herald Tribune, next to an article on kindness to animals. After seeing the picture, Mr. Probert wondered if he should change his proposed slogan of "Sleep Like a Top" to "Sleep Like a Kitten" to advertise the railroad's new wonderful cooling system - air conditioning.
Upon further investigation, Mr. Probert found that the Herald Tribune's picture, later to become known as the Chessie cat, was created by Guido Gruenewald of Vienna, Austria. Mr. Gruenewald enjoyed creating copperplate etchings of cats and kittens. He watched their various moods and attempted to catch their personalities in his etchings. He died, in 1935, not knowing that Mr. Probert would pay $5 for a copy of his drawing that would become one of the world's most well known cats and an advertising logo for well over 60 years. Although Mr. Gruenewald enjoyed a small measure of recognition late in life, he never realized the great success his works would become and, as many artists, never had the opportunity to enjoy the fame and great wealth his creations realized.
The first ad featuring Chessie appeared in the September 1933, Fortune Magazine. This ad was designed to attract business travelers to the railroads as most families could not afford the luxury of vacations and travel. Over 300 requests were received for copies of the ad within two days of its being published.