Before he was Mike D of the Beastie Boys, Michael Diamond was best known as the son of Harold and Hester Diamond. “My mom and dad were completely integrated into the New York City contemporary art world before I was born,” says Diamond of his dealer-collector parents. “Quite a number of the Rothkos that are sold at Sotheby’s today at some point went through my parents.”

After Diamond’s father died in 1982, his mother “didn’t want to continue collecting contemporary pictures,” he says, and pivoted to buying old masters. “We were all quite taken aback when all of a sudden she announced she was switching tacks completely.”

She sold the modern art and started to buy old art. Simultaneously, she sold off the antique furniture in her sprawling Central Park West apartment and bought “really bright contemporary furniture,” Diamond says.

“I think it almost seems like a cliche, where this woman’s husband dies and she immediately goes from contemporary to Renaissance and old masters,” he continues. “I’m sure there was a long line of people saying: ‘Hester what are you doing? You have this incredible collection, why would you ever switch it up?’ ”

But his mother had “this complete faith in her own point of view, and [that guided] her collecting with complete fearlessness,” he says.

After Hester Diamond’s death in February, Diamond and his brother decided to sell her old masters, contemporary art, contemporary furniture, books, and crystals altogether. The collection will be offered in standalone live and online sales as Fearless: The Collection of Hester Diamond at Sotheby’s in January.

The live evening sale will include 60 lots, with an overall value in the range of $30 million.

“The juxtaposition of styles of furniture and paintings and sculpture is honestly, very striking,” Diamond says. “It really is something that’s rare in our world, that we have people like my mom, who are so comfortable in their own point of view.”

Barnett Newman’s Tricycle
Harold and Hester Diamond started out modestly. Harold was a school teacher before he became an art dealer; Hester began as a social worker.

Soon, Harold started as a dealer and quickly acquired a series of deep-pocketed clients, including J. Seward Johnson, one of the heirs to the Johnson & Johnson fortune.

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