Ruben W. Freeman Keith was born ( Bible, Nov. 17, 1872 )-(Tombstone, Sept. 14, 1871) he died March 4, 1942 (Bible & Tombstone). Even through Sam and Belle Starr lived close to Freeman Keith in 1880, Freeman was only 8 or 9 years old, even younger than Belle's daughter Pearl.
Pearl was born in September 1868. Pearl went to school for a while in Briartown, so Freeman may have been in school at the same time with Pearl. For that matter, both Alma and Anna Arnett could have been in school at the same time as Pearl. The only school was one small room, built of part log and part rough sawed lumber. The heating was done by a large "stick and mud" chimney, however they only had school in the summer. As the school was only one room, they all would have known one another.
The fact they knew each other may not have been significant at that time. Belle Starr did not become famous until after her death in 1889 and the novel The Legend of Belle Starr" was published in New York's National Police Gazette.
Freeman could not have kept the horses for Belle and the Jesse James gang. The James gang rode in the 1870s or early 80s. Freeman did not come to Oklahoma until 1880. Freeman was only 10 or 11 when Jesse James was shot by Bob Ford (an ex member of his gang) to collect a reward of $10,000 in St. Joseph, Missouri, April 3, 1882. The gang probably disbanded in July of 1881 after an Alton to Chicago express train was robbed of $30,000 in Jackson Co. Missouri, July 15, 1881.
Freeman didn't get married and start his own home until 1892. He would have only between 18 or 19 and not yet married, without a home of his own, when Belle Starr was killed in 1889.
I don't know where William Freeman grew up. He may have lived with his father, Joel M. Keith but most likely he lived with his grandfather, James McClure, as a boy before he married. His grandfather, James McClure was a cousin(?) of Tom Starr. Maybe it was in William Freeman's grandfather's barn that the horses were kept for Belle, Cole and Younger. Charley McClure (an Uncle of William Freeman) was shot as part of some revenge killings in his own home by an outlaw gang in 1911, With all of this happening in and around him there is not much doubt William grew up with crime figures all around him.
William Freeman may have been living with his grandfather, James McClure and at 13 through 19 and he could have kept his grandfather's horses for the so called Younger/Belle gang. Also he could have kept horses for other gangs after he got married and had his own home in 1892, but Belle Starr had been dead for three years when he got married.
However, Frank James and Cole Younger may have been still been active at that time. Belle's Son, Ed Reed's gangs and other gangs were still active then. Freeman was 22 or 23 and married during the train robberies of Bill Cook gang.