Among the highlights is a Tiffany & Company Art Deco bracelet set with five Colombian emeralds, each exceeding 10 carats, alongside approximately 20 carats of diamonds. It is estimated at $300,000 to $500,000. An India-inspired Cartier necklace from the 1950s features softly contoured sapphires, emeralds, rubies and spinels — a departure from the house’s more structured aesthetic. It is one of several Cartier pieces custom-made for Ms. Gray and Ms. Stream over the years. There is also a range of smaller, more intimate objects: pinkie rings and charm bracelets.
For dealers, the sale echoes another landmark auction: that of jewelry owned by the American socialite Wallis Simpson, the Duchess of Windsor. “Most of the Duchess of Windsor’s jewelry was made for her, and it reflected her life and her style,” said Russell Zelenetz, co-owner of Stephen Russell vintage store on Madison Avenue, in a phone interview. “That appears to be the case with Gray’s jewelry, too.”
At the center of the jewelry offering is a 49.91-carat top-quality diamond ring, estimated at $500,000 to $700,000. Mr. Poindexter described the diamond as untouched, a rarity in a market that often modifies stones to maximize brilliance.
The ring, like many pieces in the collection, carries a family story. Mr. Stream recounted that his grandmother called his father requesting that he transfer funds to purchase a 70-carat diamond ring.
“He told her that instead of buying the ring, he had wanted to purchase two tugboats [they were in the marine towing business] in her name and they were a good investment,” Mr. Stream said.
That diamond, he said, was apparently later acquired by Richard Burton for Elizabeth Taylor.
A few years later, Ms. Stream called her son with another request for funds, this time for the 49.91-carat diamond — and said the purchase was not up for discussion. “My father still refers to the diamond as the tugboat diamond,” Mr. Stream said.
