He might not have known him when he lived in his first crib, but Josh has been pals with former 'Million Dollar Listing New York' man Michael Lorber for some time.
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Michael Lorber knows a lot about real estate -- he also knows a good deal about dressing as a debonair sea captain.
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Vintage Edith and Josh Flagg! Note: Edith has and will always be fierce, even if her grandson is slouching in the photo.