Thomas was born two months after the city of La Junta began construction on a new building to house the Woodruff Memorial Library. It was his family that played an important role in the history of the city of La Junta and Otero County. His grandfather, also named Thomas, was a Boston lawyer who, in 1879, acquired propery in the practically dead town of La Junta. He described the land as "...unsaleable and seemed almost valueless."
Thomas' grandfather would not make La Junta his home until 1895 but, by 1885 he had managed to acquire at bargain prices most of the property in the original town site. In 1890, when the Santa Fe Railway built locomotive repair shops and a roundhouse and moved administrative offices to its new division headquarters in La Junta the town had much potential. The wealth of Woodruff grew with the community and he generously contributed to the community's development. Schools, libraries and parks, almost every civic improvement, was in one way or another the beneficiary of Woodruff gifts.
One hundred years later, his gifts to the community continue to benefit local citizens. Most notably is that of Woodruff Memorial Library, originally the Young Folks Library, that Woodruff personally handpicked the books for in 1888. After Woodruff's death he left the library five lots that had been selected by Woodruff as the 'proper place for the location of a public library building', a check for $16,208.60 to start a building fund, property to be sold and proceeds added to the building fund, plus rental income property to be used for library maintenance.
Thomas never did meet his grandfater as he was born just one year after his grandfather's death, but the library his grandfather left behind was a tremendous asset.