In the era before easy access to photo engraving or stock illustrations, newspapers often had a staff artist. Walter Allman didn't have much interest in an early job in the grain business and he spent his time drawing on the sides of boxes and crates. Soon his talent landed a job at an engraving company and later the Toledo News-Bee. His work was picked up by the Scripps syndicate NEA Service and his comic Doings of the Duffs became a nationwide feature.
It appeared in the Telegram as a regular feature and helped give the paper a boost over the more conservative and less illustrated Tribune.
Allman was the cartoonist from 1915-1924. He died in 1924 at age 42 after suffering a nervous breakdown the year before. Ben Batsford then picked up the pen from 1925-1930.
I understand why the cartoonist drew it that way, he wanted the sight gag to read off the page but Tom Duff has the cleanest basement I have ever seen.
Fans of the Simpsons will recognize this as the original Duffman.