In 1881, he left teaching to work for the Philadelphia Press, where he was musical art and literary editor until 1878.

Returning to the newspaper business, he was editor of the Philadelphia Press from 1877 until 1880.

Following his graduation from Cornell in 1869, he worked as a journalist for the Philadelphia Press.

His father was the art editor of the Philadelphia Press while his mother was a sculptor.

Upon his return to Philadelphia, he worked as an illustrator for the Philadelphia Press until 1902.

As a captain in a black company from Pennsylvania, he sent stories to The Philadelphia Press.

In 1892, he left that newspaper and began illustrating for the Philadelphia Press.

Shinn has said of his experience at the Philadelphia Press:

After graduating, Paine worked for the Philadelphia Press until 1901.

From 1880 until his death he was editor and part proprietor of the Philadelphia Press.