Reynolds was the son of Gaines W. Reynolds, a wholesale grocery salesman, and his wife, Anna Louise. He grew up in Oklahoma City, Oklahoma and got his first job in the newspaper business selling papers at the local railroad station. In high school, Reynolds decided he wanted to attend the University of Missouri'sMissouri School of Journalism, and he worked during high school and successive summers at a meat packing plant to pay for his studies. While at the University of Missouri, he was initiated into Pi Kappa Alpha. He graduated in 1927. Reynolds' first business venture was a photo engraving plant. He then purchased and sold the Quincy Evening News in Massachusetts, using the proceeds from that sale to buy the Okmulgee Daily Times in Oklahoma and the Southwest Times Record in Arkansas. Those two papers launched the Donrey Media Group. Operating mostly in small towns, the group grew to include more than 100 businesses, including newspapers, radio stations, television stations, cable television operations, and billboard companies. Perhaps his biggest success came with the ownership of the Las Vegas Review-Journal, the largest newspaper in Nevada. Reynolds interrupted his newspaper career to serve in the military during World War II, initially in military intelligence and, later, as the officer in charge of the Pacific and London editions of the "soldiers' newspaper, Yank, the Army Weekly. He attained the rank of Major, received the Legion of Merit, Purple Heart and Bronze Star Medal during his military service, and returned to civilian status in 1945. He focused his business acumen on businesses located in small but growth-oriented communities, and these communities often were the recipients of the Foundation's earliest charitable grants. Reynolds died on April 2, 1993, on a cruise ship, on the Mediterranean Sea, at the age of 86. A large sum of money from his business ventures went to the Donald W. Reynolds Foundation. There are currently a number of buildings named for Reynolds, including:
Reynolds left three children on his death: Nancy, Donald and Jonathan. Forbes Magazine notes that Reynolds's three children will receive trust income of $50,000 a year for life, but will be left only $1 if they unsuccessfully contest his will. The bulk of the Estate was left to The Donald W Reynolds Foundation. The Donald W. Reynolds Foundation continued his lengthy legacy of charitable giving with funding programs for capital grants, aging and quality of life, cardiovascular clinical research, and journalism. In accordance with its articles of incorporation, the Donald W. Reynolds Foundation was designated to terminate rather than continue in perpetuity. Its board of trustees determined that the foundation would cease to make grants by the year 2022. In fact, the foundation liquidated its assets and closed its doors at the end of 2017.