CNN  — 

Frank Sinatra may be best remembered for his velvety voice, booze-fueled partying and associations with some of the most beautiful women in Hollywood. But he was also a romantic husband to Barbara, his wife of 22 years, an engaged citizen who befriended several US presidents, and a painter who embraced abstraction.

Glimpses into Ol’ Blue Eyes’ life – the public persona and his more private side – will be on display at Sotheby’s upcoming New York sale of the estate of Barbara Sinatra (who passed away last year) in December. Drawn from their residences in Beverly Hills and Malibu, and the house Barbara purchased in Rancho Mirage, California after her husband’s death in 1998, the more than 200 lots range from professional memorabilia to personal items that cast a new light on the performer.

Frank Sinatra with his fourth and final wife, Barbara Sinatra.

“People think of Sinatra as an entertainer, a singer and actor, somebody who liked to have a lot of fun with his friends, and a drinker, but ultimately what this sale illustrates is that he was very politically engaged and intellectual,” Mari-Claudia Jimenez, managing director of Sotheby’s Fiduciary Client Group, said in a phone interview.

The last large major Sinatra auction was held by Christie’s in 1995, when Frank and Barbara organized what they jokingly called a “garage sale” after they sold their Rancho Mirage home. That auction of 250 lots raised $2.07 million, far above the presale estimate of $1.5 million.

This December’s auction has an overall estimate of $3.5 million, though Sotheby’s is hoping the Sinatra mystique will pull in far more.

The singer and the showgirl

Barbara, a former model and Las Vegas showgirl, was Frank’s fourth and last wife. In her memoir, “Lady Blue Eyes: My Life with Frank,” she recalled how her “romantic husband went out of his way” to make her feel “loved and cherished every day, taking the time to express his feelings,” leaving little notes and cards for her to find.

The couple first met as neighbors in the early 1960s, 10 years before he finally kissed her at a party thrown by Eva Gabor. They were married in 1976.

Oliver Barker, Sotheby's European Chairman, fields bids for Andy Warhol's "Self Portrait" from 1963-64, during the Contemporary Art Evening Auction at Sotheby's on June 28, 2017 in London, England.
How do art auctions really work?
03:09 - Source: CNN

Frank’s proposal was convoluted. First, he threw two huge jewels onto the bed (including an emerald-cut 20-carat diamond) and told her to pick one. Then, after having the chosen stone set, he dropped it into a glass of champagne for her to discover.

The 20.60-carat engagement ring carries an upper estimate of $1.5 million and is the top piece of jewelry in the sale, though there are several other pieces of note, including classic designs by Van Cleef & Arpels, Bulgari, David Webb and Marina B – one of Barbara’s favorite designers.

In her memoir,  "Lady Blue Eyes: My Life with Frank," Barbara Sinatra described how her husband went out of his way to make her feel "loved and cherished every day, taking the time to express his feelings."

“He loved buying jewels for her and spontaneously surprising her in interesting ways,” Jimenez said. “There was a time when he’d put bracelets and rings in her pockets for her to find. One time, they were watching television, eating popcorn and she found a diamond ring inside the popcorn box.”

All the presidents’ friend

Frank Sinatra and John F. Kennedy at the latter's 1961 inaugural gala.

Having first met John F. Kennedy as a young senator, Frank had actively campaigned for Kennedy’s presidential bid in 1960 and helped plan his inaugural gala. The auction includes a dedicated copy of Kennedy’s 1955 book “Profiles in Courage,” signed when he was still a senator, as well as a deluxe edition of the inaugural gala program and three volumes of Kennedy’s public papers, containing messages, speeches and statements he made as president.

“The intellectual aspect of his relationship with various presidents is important. It wasn’t just about being the entertainment director. I think he felt like politics was part of his civic duties and part of being a good American citizen,” Jimenez said.

The auction also includes signed books by or photographs of Harry Truman, Gerald Ford, Richard Nixon, Ronald Reagan, Jimmy Carter, George Bush and Bill Clinton.

Frank Sinatra with President Ronald Reagan, a personal friend who he tirelessly supported.

Frank supported Nixon in 1972 on feeling the Democrats had shifted too far to the left and they developed a close friendship, holidaying together. Ronald Reagan was another friend whose presidential campaign he supported tirelessly through fundraising galas, as well as a personal donation reportedly of $4 million. Nancy Reagan can be seen in the background of a photograph taken of the Sinatras as they cut their wedding cake.

Come paint with me

While the 1995 featured several impressionist paintings and works by American artists, the upcoming Sotheby’s auction includes a few fine art paintings that the couple had kept. On offer are a 1973 Norman Rockwell portrait of Sinatra he had commissioned and posed for, and a 1938 Walt Kuhn oil on canvas, “Girl With Turban (Zuleika),” which took pride of place in the couple’s living room and reminded Barbara of her days as a show girl.

"Girl With Turban" (1938) by Walt Kuhn once hung in Barbara and Frank Sinatra's living room.

The auction also includes several abstract works painted by Sinatra himself.

“He found painting relaxing and had constructed artist studios in all of his homes,” Jimenez said. “He would mostly give them to friends and a few have come to the market. The most well-known was a work that belonged to Ronald Reagan and was sold in 2016 for $223,500.”

Jimenez notes that while Frank was more interested in collecting figurative works, as a painter he focused on abstract art, creating work in the style of artists he admired, like Piet Mondrian, Robert Motherwell and Kazimir Malevich.

“There is in the sale a couple of clown paintings that are meant to be more allegorical about how he felt as an entertainer wearing a mask on stage, but that is the only time really when he’s done something more figurative,” Jimenez said.

The estate sale will be offered over three separate events: Lady Blue Eyes: Property of Barbara and Frank Sinatra, Lady Blue Eyes: Online, and finally as part of the Magnificent Jewels sale.