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."
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.
"When I was born, my dad was starting to do much better in his business," Diamond says, "and so I had this incredible childhood where I was able to grow up around really amazing modernist pictures, because my dad dealt at home."
The walls were filled with works by Fernand Léger, Pablo Picasso, Mark Rothko, and Barnett Newman, and the dwelling was filled with those artists, who often swung by for visits.
Yet the siren song of St. Marks Place was too loud for the teenage Diamond to ignore.
"Even though it seemed relatively cool to be in an apartment with Rothkos on the wall-and Barnett Newman riding a tricycle around the apartment-being a punk-rock kid, I couldn't wait to get downtown. It all seemed pretty square," he says. (Newman was not a tall man; the tricycle belonged to Diamond's brother.)
Still, Diamond says that his parent's lives affected his professional trajectory.
"I think the biggest gift I grew up with in that apartment in the El Dorado was that my opinion mattered. That was really, really important," Diamond says. "It made it seem like, of course I'm in a band with these kids I grew up with, and we want to make rap music because that's all we listen to. Then of course, we can do that, too."
Hester, for her part, devoted nearly 40 years to old masters, even as she crisscrossed the globe attending avant-garde art music recitals, attending Wagner's Ring cycles, and meeting artists young and old.
"My mom was a practitioner of what I would call 'the immersion practice,'" Diamond says. "She was not a dip-her-toe-in-the-water kind of person; it was sink or swim for her."
There was no lag, he continues, between her initial excitement about old masters and "her literally diving in and learning all she could learn, whether it was going to museums or talking to academics. She'd collect and continue to refine and upgrade her collection as she went along."
Among other endeavors, she was the founding president of the Medici Archive Project, a research institution dedicated to studying the 200-year epistolary collection of the Medici grand dukes. She also donated numerous paintings to museums as her collecting evolved.
This passion continued "really, until the end of her life," says George Wachter, co-chairman of old master paintings worldwide at Sotheby's.
He recalls when a pair of sculptures went to auction in Paris last year, Hester had already been diagnosed with cancer. "I discovered she was the underbidder for them in Paris, for $1.9 million," Wachter says, meaning that she'd bid for them at auction but didn't win. She had submitted the bids while in a treatment facility in Germany.
"She was three to four months from dying, but she had a hunger-she was fearless. She had never seen these sculptures, but she loved them and decided on her own, unprompted, to buy them."
Now, buyers around the world will have a chance to sample a bit of Hester Diamond's taste for themselves.
The lead lot of the sale is Autumn, a sculpture by baroque artists Pietro and Gian Lorenzo Bernini. Estimated to draw from $8 million to $12 million, the work is "jaw-dropping," Wachter says. "I don't think there are many [sculptures by Bernini] in America altogether. There's one at the Met, one at the Getty-but not many, and certainly not one that's secular like this. It's an amazing thing to have."
Other major works include a triptych by the Flemish master Pieter Coecke van Aelst from about 1520, which carries an estimate of $2.5 million to $3.5 million, and two large paintings by Italian Renaissance painter Dosso Dossi, which had been painted for Alfonso I, duke of Ferrara, in the early 1500s. Those carry an estimate of $3 million to $5 million.
There is also a series of contemporary artworks, including a video installation by artist Bill Viola called Ablutions (estimate: $70,000 to $100,000) and a sculpture by contemporary artist Dustin Yellin.
Apart from a massive collection of art books, "at a certain point, she also got absolutely riveted by minerals," Wachter says. "These rocks are really colorful, and she has about 100 of them. And some of them are relatively valuable; we're going to have about 10 of them in the live sale."
Also included in the sale is a selection of Beastie Boys memorabilia from her collection. "It's just trying to capture her vibe-what she loved and cared about," says Wachter.
Despite the current uncertainty of the art market-such factors as the forthcoming presidential election could impact buyer sentiment-Wachter says he's confident that the sale will be a success.
"I feel like this is a whole different ballgame," he says. "This is a great collection. I was practically a nervous wreck for two weeks when I was waiting for [her family] to decide who [they were] going to give it to [to sell.]" The collection, he continues, "is a really special group. She didn't care about the name of the artist, she cared about the beauty of the object-and that's just something that's a fact."
"One thing I loved later in life was going to museum and art exhibitions of all kinds with my mom," he says. "If we'd see something she was less than captivated by, she could speed walk through a major art museum like no one you'd ever seen. She was not interested in wasting her time."