Reynolds was the son of Gaines W. Reynolds, a wholesale grocery salesman, and his wife, Anna Louise. He grew up in Oklahoma City 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's Missouri 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.
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.” He attained the rank of major, received the Legion of Merit, Purple Heart and Bronze Star 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 in 1993, and 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 the Donald W. Reynolds Razorback Stadium, the D. W. Reynolds building at Hendrix College, the Donald W. Reynolds Performing Arts Center at the University of Oklahoma, the Donald W. Reynolds Performance Hall at the University of Central Arkansas, Donald W. Reynolds YMCA in Warren, Arkansas, the Donald W. Reynolds Alumni Center and the Donald W. Reynolds Journalism Institute at the Missouri School of Journalism, the Donald W. Reynolds School of Journalism at the University of Nevada, Reno, the Donald W. Reynolds Center at the University of Tulsa, the Donald W. Reynolds Center for Business and Economic Development at the University of Arkansas at Little Rock, the Donald W. Reynolds School of Architecture at Oklahoma State University, and The Donald W. Reynolds Campus and Community Center at Southern Arkansas University in Magnolia, AR.
Donald Worthington 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 continues his lengthy legacy of charitable giving with funding programs for capital grants, aging and quality of life, cardiovascular clinical research, and journalism.
Reynolds was often praised for his visionary business skills, since he bought rural newspapers, helping to keep them in print. However, critics often cite the fact that the Donrey Media Group paid wages lower than industry standards, making it difficult to attract and retain good people. Turnover at Donrey papers tended to be very high. But he was also known for his cruelty when it came to the bottom line. Forbes called Reynolds remarkably "consistent in ruthlessness," with "a single-minded devotion to business," with "not much use for compassion." He even bragged about breaking the legs of a union protestor at his photoengraving plant by running him over during a labor dispute.