Toby Casteel was the husband of Annie Brandywine, father of Luke Casteel and four other sons, who are in prison. He is also the step-grandfather of Heaven and grandfather of Tom, Fanny, Keith and Jane as well as great-grandfather of Darcy Wise and Luke Casteel Jr.
Toby met Annie when they were both 14 and they married and had their five sons, one of them being Luke Casteel. In old age Toby would often whittle using a knife and wood whilst his wife knitted and looked after their grandchildren. When Annie dies, Toby loses his sense of reality and spends years thinking Annie is still alive until he eventually dies of old age at the end of Dark Angel.