While Hess was riding with fellow U.S. Deputy Marshal George Lawson of the Eufaula District on December 4, 1896, the two planned to arrest Dan “Dynamite Dick” Clifton, the last of the Doolin Gang, who they knew to be hiding out on Sid Williams’ farm about sixteen miles from Newkirk, Oklahoma. However, when they found the outlaw, Clifton fired on them with his rifle, and Lawson returned the fire hitting Clifton in the arm and knocking him from his saddle. “Dynamite Dick” then fled through the woods taking refuge in a small cabin. In pursuit, the lawmen trailed him to the cabin, and when the injured Clifton tried to escape again, he was gunned down by the two officers and died just moments later.
Two years later, in February 1898, when Bussey and U.S. Deputy Marshal Gabe Beck were attempting to arrest members of the Miller Gang at Inola, Oklahoma, both lawmen were shot, and the Cherokee Advocate in Claremore, Oklahoma reported they had both probably been killed. However, that was not the case, as both officers survived.
Just two months later, on March 17, 1898, Hess was riding with fellow U.S. Deputy Marshal William Arnold at Claremore when the two tried to arrest a man named Bill Johnson, who resisted. When Johnson shot and killed Deputy Arnold, Hess Bussey returned the fire and killed Johnson.