He was known throughout the West by the soubriquet "Prince Hal", and for a variety of comments made by Simpson about Hallowell's "silk socks".

According to historian O. Gene Clanton, Simpson "won the respect and admiration of his colleagues in the House, regardless of party," and his performance in Congress "was, from beginning to end, principled, consistent, and commendable".

Louis F. Post of The Public: A Journal of Democracy wrote that "many absurd stories in explanation of this epithet have been told in print.

From that point forward Simpson campaigned as "Sockless Jerry," spinning his lack of hosiery into the elusive political gold of authenticity.

Colonel Hallowell is a brilliant, experienced and competent man who would add strength to the Kansas delegation; Jerry Simpson is an ignorant, inexperienced lunkhead … who would disgrace the state in congress; scarcely able to read and write, unacquainted with public affairs, without experience as a legislator, raw, boorish, [and] fanatical with the fanaticism of sheer ignorance".

[4] Hallowell died in Crawfordsville, Montgomery County, Indiana, June 24, 1898 of complications relating to consumption.

The funeral of Col. James R. Hallowell occurred on a Sunday afternoon in the residence of Mrs. Laura Doubleday on West Main Street, and the service was attended by a large number of citizens and soldiers from Pennsylvania, Kansas, and Indiana.