In the mid-1990s, Chester was dating a woman named Elka Brand. Together they welcomed a son, Jimmy, but decided they no longer wanted to be together. At that time, Chester also decided to adopt Elka’s other son, Ischia, in an effort to keep the two brothers together.
Chester married his first wife Samantha in 1996, and they welcomed Draphine Sebastian in 2002. Three years later, Chester and Samantha got a divorce.
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