Such was the fate of Bill Doolin, whose gang battled U.S. Marshals in one of the most historic shootouts in the West in 1893. Marshal Heck Thomas tracked Doolin for three years, finally ambushing and killing Doolin on a quiet country road in northeastern Payne County.
Another famous lawman was Bass Reeves, believed to be the first African American deputy marshal west of the Mississippi River. A tough and fearless man, Reeves served for 35 years, longer than any lawman on record in Indian Territory.
Reeves was born into slavery in Texas but escaped to Indian Territory before the Civil War. Reeves was one of 200 deputies commissioned by Judge Isaac C. Parker, the "Hanging Judge," after 1875 to track down criminals in lawless western Arkansas and Indian Territory. Many Indians distrusted white deputies, so Parker believed blacks would be particularly effective lawmen in Indian Territory.
Associated with the Doolin Gang were a few female outlaws, including one of the most famous bad women of all times, Belle Starr.
Judge Parker sentenced Starr in 1882 to federal prison on a horse-stealing charge. After her release, Starr lived quietly on her homestead near Eufaula, until she was murdered on a road one wintry day. Starr's killer has never been brought to justice.