Winford Rhinehart is an important character in Shipwrecked and Single, one of the pre-made neighborhoods in The Sims Castaway Stories. He is a survivor who winds up stranded on the island and is found by the player. He gives the player and other castaways food, but in the end, it appears he has different plans.
At first, he appears to counsel and help the player. He even makes sure that they build their raft in order to return to civilization. When the player has finished building the raft, a mysterious firestorm occurs. It is later revealed by Bart Pittman, in his last breath, that in the end, Winford is responsible for the Queen Solomon's shipwreck. After the player's Sim confronts him, he admits that he had been to the island before and he ultimately only wants eternal youth. He blackmails the player's Sim with their lover's death, claiming to have found an antidote for the disease that infected them. In the end, using the Staff of Tazu at the Sanctuary of Tazu, the player's Sim opens Rhinehart's way to eternal life.
Once Winford drinks from the Chalice of Youth, the player's Sim is given the choice either to banish Rhinehart or reward him by giving him youth, ironically by turning him into a toddler, guided by Amanaki Tama. Either way, the original Dr. Rhinehart is never seen in the game again, unless cheats are used. In the end of the story, a package arrives for him, which contains a weather controlling machine. The player's Sim receives the package instead of him.
- Winford's hair changes during his visible life stages. When he is an elder, he has grey hair. When he is an adult, he has blond hair, and when he is a toddler, he has red hair. Howewer, his genetics are for brown hair.
- Although Winford can be turned into a toddler, he is actually an adult with a toddler appearance. This can be fixed in SimPE, by changing the "Adult" tag to the "Toddler" tag, and changing the aspiration to "Grow Up".
- He greatly resembles Julius Caesar, a deceased Sim from Veronaville.