James Haller Ottaway, Sr., turned his 1936 purchase of a New York semiweekly into a small chain of medium-sized but immensely profitable newspapers that he sold to Dow Jones in 1970 for $37 million in stock. By the 1980s Ottaway's worth had skyrocketed to more than $250 million as he earned a prominent place on the Forbes list of the four hundred wealthiest Americans. None of Ottaway's papers was known for exceptional editorial quality--a Pulitzer Prize was never awarded to an Ottaway newspaper.

However, the Ottaway newspapers always strove to be close to the small communities they served, and most turned out to be enormously profitable. After Dow Jones bought the chain, Ottaway began to serve on the company's board of directors, engineering the purchase of ten additional community newspapers. In 1984 Ottaway retired from the board of directors of Dow Jones and Ottaway Newspapers, but he continues to serve as an acquisition...