One day last week, an armored car drew up before a six-story building on Manhattan's East 51st Street. Out stepped a mail carrier clutching a brown-wrapped package. Entering the building, he plunked the package on the reception desk of Jeweler Harry Winston.

Small (5 ft.), swarthy Harry Winston, one of the leading U.S. diamond dealers, thus took possession of his biggest buy this year — the famed gem collection of Washington's onetime No. 1 hostess, the late Evalyn Walsh McLean. As usual, he had shipped it to himself by mail (postage: $159.87,...

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