Singson started out as a businessman owning tobacco factories manufacturing and distributing Virginia tobacco, a bus transportation company named Partas,a construction company, a radio station, an ice plant, and a tomato paste plant.
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Chavit considered his uncle, Floro Crisologo as a mentor, but eventually had a severe falling out with his cousin and once-confidant Vincent "Bingbong" Crisologo (who was Floro's son) and there were many bloody encounters between the two.
In September 2009, it was reported in the news that he had an affair with Rachel Tiongson at a time that she was still cohabiting with Chavit Singson.