John "Jack" Knowles, former owner of the Hillsboro Sentry-Enterprise, died May1, 2022, following a battle with vascular dementia. He was 85.

Knowles spent the first 30 years of his journalism career at the Chicago Tribune, starting as a copy boy at 18 years old and working up to editor of the foreign news desk. He left the newspaper in 1989, moving his young family to a small farming community in Wisconsin and purchasing the Sentry-Enterprise. Knowles sold the newspaper to Morris Newspaper Corporation of Wisconsin in 2004.

Paula Kay (Davel) Fredrickson, a longtime writer for The Dodgeville Chronicle, died on May 15, 2022, following a brief illness. She was 76.

After studying journalism at the University of Wisconsin-Eau Claire, she was hired by the Blanchardville Chamber of Commerce to write stories about local businesses. She began her 38-year newspaper career with the Blanchardville Blade-Atlas, and went on to work for The Dodgeville Chronicle, The (Mineral Point) Democrat-Tribune, and the Pecatonica Valley Leader. 

Jon Nels Olson, a longtime reporter and editor who lived in Milwaukee,  died on on Thursday, May 19, 2022, of complications from Myotonic Dystrophy following a fall from his bicycle during the previous month. He was 63.

Olson began his career as the editor of the Middleton Times-Tribune before moving in to work as a reporter and associate editor of The Business Journal. He also produced the television show Business of Wisconsin. He worked as a business reporter for the Milwaukee Journal from 1991 to 1995 and then as a copy editor from the Milwaukee Journal Sentinel from 1995 to 2009.