Creating a low-cost auto insurance company that sells to those who traditionally can’t afford coverage and then employing cost-effective tactics when it comes time to payout claims has been a successful formula for Chicago’s Richard Parrillo. The prominent insurance magnet, with an estimated net worth of $158 million – relatively modest compared to others in his Lincoln Park neighborhood – is about to test his gilded touch. Parrillo put his Burling Avenue mansion on sale for $50 million -- $18 million over the highest asking price for any residential real estate in the Chicago area and more than double the highest price ever paid in the region.

