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Not much is known about Chester's past, but it is possible that he moved from another town to Moonlight Falls because he divorced with his wife, or because the latter died. Chester Swain is very overprotective of his daughter, as seen in his bio.
He is a Sim spoof of Twilight character Charlie Swan: both have first names that start with "Ch" and similar-sounding last names, are single fathers, love fishing and work in Law Enforcement. However, Chester's secret wish to work in Business is exclusive to the spoof.
Another similarity is their zodiac signs, both Chester and Billy Burke (who played Bella's father) are Sagittarians.