At the end of 1863 and again in late 1864, the Confederate guerrillas of western Missouri trekked south to Texas for the winter. (Winter was the most dangerous season for them, as snow on the ground and a lack of cover made tracking far easier for Union forces.) This photograph shows three bushwhackers enjoying themselves during their long holiday. Two of these men, Archie Clement (1) and Dave Pool (2), were close friends and allies of Jesse James, during and after the war.

When Jesse first joined the bushwhackers at age sixteen, Clement was one of his leaders. Later, Clement served as chief lieutenant to William "Bloody Bill" Anderson (whose band Jesse soon joined), and earned a grim reputation for scalping and dismembering dead Union soldiers. Clement took command of most of Anderson's followers after Bloody Bill's death in late 1864. In 1866, Clement led his followers into a direct confrontation with the Radical state government, culminating in the occupation of the town of Lexington on election day and a wild gunfight with militiamen sent to arrest him. The episode ended in Clement's death. A decade later, Jesse James still voiced anger at Clement's fate.

Like many of the bushwhackers, including the James brothers, Dave Pool belonged to a prominent family in the prosperous Missouri River valley. He too took part in the 1866 occupation of the town, but it appears that he soon abandoned the bushwhacker life. However, he continued to give aid the James brothers after the war.