From February to May 1880, Anderson stole horses from the Mescalero Apache reservation as well as cattle from ranchers on the Colorado River to whom they sold for $10 a head to White Oaks businessman Thomas Cooper.
Later meeting up with Dave Rudabaugh, the three rode into White Oaks the following day and attempted to gun down deputy sheriff James Redman but were forced to flee after a crowd of 30 or 40 local residents took to the streets.
Following the siege at Stinking Springs (near present-day Taiban, New Mexico), he was arrested with the rest of Billy the Kid's gang after surrendering to Pat Garrett and convicted in December 1880.
Thanks in part to the efforts of Pat Garrett and others, Anderson received a presidential pardon from President Grover Cleveland in 1896 and worked as a U.S. customs inspector for a time.
Serving as sheriff of Terrell County, Anderson was eventually ambushed and killed by cowboy Ed Valentine when he responded to a call at a local saloon in Sanderson.