Cass was born into a bad family. Cass' father died of a heart attack and his mother, Claudia, disowned him due to a childhood event. One of Cass' brother died of the same disease that would almost claim his daughter's life. Cass is the brother to Morgan and Stacey Winthrop. Cass is an attorney. Cass is known to be a cassanova with the ladies. He began seeing Felicia Gallant, a romance novelist, in the early 1970's. When Cass came to Bay City in 1982, he resumed his fling with Felicia. However, the cassanova part of Cass got to him, and he cheated on Felicia with Cecile de Poulignac. However, that did not last a while. Cass fell in love with Kathleen McKinnon in 1984. A year later, they were engaged. Cass' marriage to Kathleen was delayed because she was paralyzed by Carl Hutchins. However, on their second chance to the altar, Cass was kidnapped by Cecile and became a love slave to her in Tanquir. After that ordeal, Cass and Kathleen were married.
However, Kathleen was "killed" in a plane accident, which Carl planted a bomb on. Cass returned to Bay City after grieving for Kathleen. However, Bay City did not realize that their favorite friend, Cass, was not Cass at all. It was Rex, Cass' evil lookalike. Rex tooked over Cass' life and eventually fell in love with Nicole Love. However, Cass "killed" Rex and regain his life. Cass and Nicole were about to be married, but Frankie Frame proved that Nicole was the one who killed Jason Frame, her uncle. Cass and Frankie became a super couple. Cass and Frankie became engaged. However, in Frankie and Cass' first attempt to become man and wife, Frankie was kidnapped. After Frankie was recovered, Frankie and Cass were married. Frankie found out that Cass' dead wife, Kathleen, was still alive. Frankie made Cass choose, and he chose Kathleen. Cass did not know that Frankie had been pregnant with his child and later miscarried. Cass and Kathleen relived their comic adventures. However, after Frankie was "killed" in the Lady Killer video by Carl, Cass went back to Frankie.
Cass was poisoned by Frankie's best friend, Christy. Cass and Frankie were later married in Italy and conceived a child, Charlie. Charlie developed the same child that claim his brother. Cass developed manic depression and had to be admitted into the hospital. Today, Cass still takes his medicine for his disease. In 1996, Cass suffered another loss when The Bay City Stalker claimed his wife, Frankie Frame. He grieved for months and months. Cass still mentions his beloved Frankie. In 1998, Cass has consumed his life with someone's sick plan of renacting Felicia's novel, Embers in the Snow. Cass is fearful for his life because his character dies in Chapter 13. Also, Cass has developed a flirtatious relationship with Lila Roberts. Sparks seem to fly whenever the two are around each other.