James Stilwell was born in 1920 in Texas and moved to Klamath Falls in 1931 with his parents Fred and Ica Mae and 7 brothers and sisters. His school years passed at Riverside Elementary and Klamath Union High, where he graduated in 1938. He was enrolled at Armstrong College in Berkeley, California, but left it to enlist in the U.S. Navy following the bombing of Pearl Harbor. He was stationed from 1942 to 1945 in Navy Intelligence in Southern California. During his lifetime Stilwell did various jobs like loading hay at a Poe Valley ranch, hawking newspapers, driving dump trucks, and, after his discharge from the military, working as an accountant with Southwell & Stilwell. In 1957, he launched his real estate business, James F. Stilwell & Co., as a broker and private investor, where he worked until his retirement in 2000. In 1961, Stilwell was asked to lead a campaign to build a new, updated hospital. As the General Chairman of the 1963 Campaign to raise funds, he managed to raise $1.3 million in 15 months. Initially the hospital was named Presbyterian Intercommunity Hospital, when it opened in 1965. Then in 1979 it was renamed the Merle West Medical Center after Merle West Trust which gave the hospital $1 million. James Stilwell had been disappointed with this decision as it honored just one individual instead of many, who helped build the hospital. In 2007, the hospital was given its current name of Sky Lakes Medical Center. As realtor and investor, James Stilwell specialized in commercial and industrial properties. He helped form a Babe Ruth baseball league, was key person in creating the Shasta Plaza Shopping Center (now the Klamath Mall), has assisted in reopening the Esquire Theater as the Ross Ragland Theater, and in creating many downtown, South Sixth Street and Washburn Way businesses.