Caleb was born to Scarlett and Carlos Winifred, along with his older twin sister, Mary. His younger siblings, Opal and Gerard, were born shortly after. Ever since he was a little boy, he had wanted to join the military, against his father's wishes. His father wanted him to be an athlete.
In The Sims, Caleb is an old man and lives in a different house that in The Sims 3 with his younger second wife and his son with her, William. He is a General in the army, despite his old age.
In The Sims 3, Caleb has a large family, but loses his wife and a daughter to a house fire. Shortly after, he marries a much younger woman, Rosa, and has a child, William.