A Preview of the Nearly $2 Billion Worth of Art Set to Hit the Auction Block in May

May 12, 20229 min read
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Key takeaways

  • The marquee evening sales that the three biggest auction houses – Christie’s, Sotheby’s, and Phillips – each hold in New York every May are often considered bellwether indicators for the future direction of the art market due to both the sheer volume and high quality of the works on offer. 

  • This season, in addition to the traditional marquee sales featuring blue-chip Impressionist, Modern, and Contemporary art, Sotheby’s and Christie’s are each staging standalone, single-owner sales from two of the best collections of contemporary art in recent memory. Many of the leading works from across the series of sales are expected to achieve record-setting prices, with close to $2 billion expected to flow into the art market as a result over the next two weeks. 

  • At times of volatility in the broader financial markets, collectors often regard fine art as an investment hedge since art values don’t necessarily follow the direction of the stock market. Additionally, examinations of past cycles in the art market have shown that art prices generally tend to rise during high inflationary periods.
Banksy’s ‘Choose Your Weapon’ (2009). Spray paint and emulsion on board, in two parts, 93 ¼ by 96 ⅛ inches. Image courtesy of Sotheby’s. 

This spring, Yieldstreet is proud to be working with The Canvas, the premium art market newsletter, to deliver in-depth analysis surrounding the blue-chip contemporary art market and the marquee May sales in New York. If you’d like to receive more exclusive coverage from The Canvas to get access to the same insightful reporting that the art world’s top collectors rely on to navigate a rapidly shifting art market, we encourage you to join their insider community by subscribing here

Marquee May sales in New York 

For the art market at least, the month of May can mean only one thing: the arrival of the marquee evening sales that the world’s three biggest auction houses – Sotheby’s, Christie’s and Phillips – each stage in their New York salesrooms. The auctions feature masterpieces by blue-chip stalwarts such as Picasso, Monet, and Warhol; as well as fresh, in demand pieces by many of the art world’s most highly sought after young contemporary artists.

This season, both Sotheby’s and Christies are hosting historic single-owner sales in addition to their usual offerings of Impressionist, Modern, and Contemporary highlights. Christie’s has the collection of Thomas and Doris Ammann, the sibling co-founders of the Zurich-based gallery, Thomas Ammann Fine Art. Both siblings are now deceased, and their collection featuring some of the finest works by Andy Warhol, Cy Twombly, Robert Ryman, Brice Marden and Sigmar Polke is being sold with proceeds from the sales going to charities supported by their eponymous foundation. 

Meanwhile, over at Sotheby’s, the auction house will offer the second half of the historic Macklowe collection, the first half of which achieved $676.1 million when it was sold last fall. The artworks featured in the two-part sale include some of the very top artists of 20th and 21st century and are a reflection of the exquisite personal tastes of real estate tycoon Harry Mackowe and his ex-wife, Linda. 

Both sales – in addition to each auction house’s respective Impressionist, Modern, and Contemporary evening auctions, as well as the 20th Century and Contemporary Art Evening auction at Phillips – contain a surfeit of high-quality works, many of which are expected to achieve record-setting prices with close to $2 billion expected to flow into the art market over the next two weeks as a result. 

As The Canvas previously reported in our first article with Yieldstreet, the art market is currently riding a wave of significant upward momentum that has left many in the industry looking to this season’s auctions as a bellwether indicator of the wider health of the international art market. Below, we dive deep into some of the major highlights of the season in order to give Yieldstreet’s investors an insider’s preview for what to expect before all the excitement is set to go down. 

Female & artists of color expected to shine

Christie’s 21st Century Evening Sale, scheduled for Tuesday May 10th, features defining artworks from a diverse array of artists who are helping to define the direction that the art world is heading in. Many of these artists are also featured in Yieldstreet’s Art Equity Funds. 

The second lot of the sale is a 2018 portrait by the Ghanaian painter, Amoako Boafo, currently one of the most sought-after artists in the contemporary art world, whose works are in the permanent collections of leading museums such as the Guggenheim and the Los Angeles County Museum of Art; and who last year collaborated with the Jeff Bezos-owned aerospace company Blue Origin to launch three of his works into space. 

The painting that Christie’s has on offer, ‘Yellow Dress’ (2018), depicts an emotionally intense subject sitting alone at a table, engaged in an intense stare with the viewer. It formed at least part of the inspiration for fashion designer Kim Jones’s Summer 2021 collection ‘Portrait of an Artist’ for Dior, with this painting in particular featured on garments included in the runway show that season. Estimated to sell for between $250,000-$350,000, ‘Yellow Dress’ possesses all the attributes of Boafo’s signature finger painting style in which he applies a mix of pigments and linseed oil to the surface of the canvas with his fingers. 

Through his practice, Boafo sets out to cast the everyday people in his life in a celebratory light while highlighting the Black faces that are often missing from art history. In the past, Boafo’s work – specifically portraits done with a yellow palette such as this one – have far exceeded their pre-sale estimates. In December 2021, for instance, Boafo’s painting, ‘Hands Up,’ sold at Christie’s for approximately $3.3 million, roughly 10 times its pre-sale estimate. 

Another work offered in the same sale is Glenn Ligon’s ‘Stranger #57’ (2012), estimated to sell for between $600,000-$800,000. This conceptual monochrome black painting intricately utilizes text and texture to explore the vastness of the Black experience by addressing black history, aesthetics, and identity. ‘Stranger #57’ is a prime example of the artist’s ‘Stranger’ series which he began in 1996 and draws its text from James Baldwin’s 1953 essay, “Stranger in the Village”. Other works from the same series are in the permanent collections of the Centre Pompidou in Paris, MoMA in New York, and the Art Institute of Chicago. 

Meanwhile, in Phillip’s 20th Century & Contemporary Art Evening Sale, one of Yayoi Kusama’s highly regarded ‘Infinity Net’ paintings, ‘Untitled (Nets),’ is up for sale with an estimate of $5 million-$7 million. Painted in 1959, this particular painting is an excellent example of the artist’s labor-intensive process in which she obsessively covers her canvases with marks of paint to form a hypnotic repetitive pattern that seems to extend into infinity. It was originally acquired directly from the artist by the German sculptor Günther Uecker.

Yayoi Kusama’s ‘Untitled (Nets)’ (1959). Oil on canvas, 51 1/2 x 45 7/8 inches. Image courtesy of Phillips

The Banksy of it all

The market for works by Banksy reached a fresh peak last October when the artist’s infamous half-shredded painting ‘Love is in the Bin’ sold for $25.4 million at Sotheby’s in London. Seven months later, both Sotheby’s and Christie’s each have works by the world’s most well-known anonymous artist up for sale. 

At Sotheby’s, Banksy’s 2009 work ‘Choose Your Weapon,’ the only material reproduction of the celebrated original graffiti that mysteriously appeared on the walls of a South London bar overnight, is estimated to sell for between $6 million – $8 million. And at Christie’s, the 2010 ‘Diamond In The Rough,’ which Banksy painted on a steel and glass truck door, is available with an estimate of $3 million – $5 million. Both works have references to Keith Haring’s instantly recognizable cartoon iconography, connecting Banksy’s urban works  to a larger body of political street art that transcends borders and spans history. 

Banksy’s ‘Diamond In The Rough’ (2010). Spray paint on truck door, 75 7⁄8 x 36 5⁄8 x 4 inches. Image courtesy of Christie’s. 

Warhol Mania

No auction season would be complete without at least one work by America’s most famous artist. Andy Warhol is currently the subject of a reviving swirl of interest in both his personal life and work; admittedly a somewhat bizarre phenomena, given that the artist died  decades ago, but one that is reaping untold benefits for those lucky enough to have his works in their collections. 

The most famous of the Warhol works on offer this season,‘Shot Sage Blue Marilyn,’ was the highlight of the single-owner sale of the collection of Thomas and Doris Ammann at Christie’s that took place Monday evening and sold to the mega-dealer Larry Gagosian a jaw-dropping $195 million (including fees). The 40 x 40 inch turquoise painting now has the record for the highest sale price for any American artwork ever sold at auction. 

Other Warhol paintings on offer this season include the macabre 1976 work ‘Skull,’ which carries an estimate of $25 million – $35 million and will be offered in Christie’s 21st Century Evening Sale on Tuesday May 10th. And finally, the artist’s camouflage-toned ‘Self Portrait,’ which Warhol painted just months before his death, is being sold by Sotheby’s as part of the second tranche of works from the famed Macklowe collection. This quintessential Warhol, offered with a $15 – $20 million estimate, is from the artist’s ‘Fright Wig’ series, Warhol’s final body of work. 


If there’s anyone who could potentially wrest away the crown from Warhol as America’s most famous artist, it would be Jean-Michel Basquiat. And given that the price ceiling for the late artist’s works has only continued to steadily rise throughout the pandemic, it should come as no surprise that both Christie’s and Phillips have two important Basquiat works on offer in the coming weeks. 

A highlight of Christie’s 21st Century Evening Sale, Basquiat’s ‘Portrait of an Artist as a Young Derelict’ carries an (on-request) estimate in the region of $30 million. This rare work, a tryptic of painted wood panels, features all of the artist’s celebrated motifs including his signature three-pointed crown and his anatomical studies; and perhaps most importantly was created in 1982, the year that most scholars consider to have been Basquiat’s best, when the young artist was at the height of his artistic prowess. 

And yet, despite its importance, ‘Portrait of an Artist as a Young Derelict’ is dwarfed – at least in scale – by the mammoth eight feet tall, sixteen feel wide painting ‘Untitled,’ (which the artist also created in 1982) that Phillips is offering with an estimate of $70 million as the star lot of its 20th Century & Contemporary Art Evening Sale. 

Regarded as one of the artist’s singular greatest masterpieces, the enormous painting comes to auction from the collection of Yusaku Maezama, the Japanese billionaire and self-professed Basquiat aficionado, who in 2017 bought a different large-scale painting by the artist for $110 million, which to this day remains the highest price ever paid for a Basquiat work at auction.

Jean-Michel Basquiat’s ‘Untitled’ (1982). Acrylic and spray paint on canvas, 94 1/4 x 197 1/4 inches. Image courtesy of Phillips.

In all likelihood, most of us will never be able to afford the sky-high prices that Basquiat’s ‘Untitled’ is expected to achieve when it will be auctioned next week. Luckily though, high quality, original works by all of the aforementioned artists have either already been or are expected to be included in Yieldstreet’s Art Equity Funds. So even though you won’t be taking home that massive Basquiat painting to try and find a place for it in your living room, thanks to Yieldstreet, you can still participate in the rise of these artists’ markets.

Learn more about the ways Yieldstreet can help diversify and grow your portfolio.