following the death of his father in 1894, riley began regretting his choice not to marry or have children. to compensate for this, he became a doting uncle, showering gifts on his nieces and nephews. he had repurchased his childhood home in 1893 and allowed his divorced sister, mary, his widowed sister-in-law, julia, and their daughters to live in it. he provided for all their needs and spent the summer months of 1893 living with them. he took on his nephew edmund eital as a personal secretary and gave him a $50,000 wedding gift in 1912. riley was well loved by his family.