VISITING THE NATIONAL PORTRAIT GALLERY for the first time in 2006 turned out to be a meaningful experience for Wayde McIntosh. Studying for a BFA in painting at the Maryland Institute College of Art, he made the short trip from Baltimore to Washington, D.C., specifically to see the inaugural exhibition of the Outwin Boochever Portrait Competition. Fifty-one portraits were on display, including “Sam and the Perfect World” by David Lenz, the first prize winner.

The portraits were made by a diverse slate of artists from across the United States, each approaching their subjects in unique and innovative ways. Walking through the show, McIntosh was so moved by what he saw, he thought, “I wish I could be in this show.” But he didn’t believe it was possible. He recalls the experience in the video below.


WAYDE MCINTOSH, “Legacy,” 2017 (oil on Dibond). | © Wayde McIntosh, Collection of the artist


More than a decade later, a friend encouraged McIntosh to enter the competition, which occurs every three years. His doubts remained, but he went ahead and did it, submitting a portrait of Jordan Casteel to the 2019 Outwin Boochever Portrait Competition. His goal all along was to get into the show. The jurors were impressed. He not only got into the show, he tied for third prize.

When “The Outwin 2019: American Portraiture Today” exhibition opened, McIntosh said he dreamed about showing at the Smithsonian museum, calling it a “historic institution.” The exhibition is on view through Aug. 30, 2020.

It’s been an “amazing ride” he said on Instagram, describing the other finalists in the exhibition an “astounding” group of artists.

McIntosh, who lives and works in Brooklyn now, was recognized for “Legacy” (2017), a small painting he made of Casteel in 2017. She is his friend and a fellow Yale alum. (He earned an MFA from Yale in 2013. She completed hers in 2014.) Casteel is also a celebrated portrait painter.

Born in Denver and based in Harlem, Casteel is known for depicting people who aren’t ordinarily the subjects of paintings—people on the subway, local business owners, people around her neighborhood, African American men, in particular. “Jordan Casteel: Returning the Gaze,” her first major solo museum exhibition is currently on view at Stanford University’s Cantor Arts Center.

In the video, McIntosh says his painting of Casteel “deals with a lot of the social issues currently going on in the United States and have been going on since the birth of the United States.”

Wayde McIntosh says his portrait of Jordan Casteel “deals with a lot of the social issues currently going on in the United States and have been going on since the birth of the United States.”

Measuring about 8 x 10 inches, the portrait has a photographic quality, is rich in narrative detail, and depicts the artist’s real space (see last image). A framed image of the March on Washington is displayed on the wall. A bookshelf full of books dominates the background. Many of them are art books; One volume is about Van Gough. There’s a red, black, and green African American flag tucked between books and an issue of Time magazine can be seen, featuring “Black Lives Matter” on the cover.

The title of the portrait, “Legacy,” references her family’s intergenerational commitment to activism, civil rights, and the arts. Her mother, Lauren Casteel, is a foundation leader whose spent her career providing a voice and opportunities for underserved populations, including women, children, people of color, and the economically disadvantaged. In 2014, she was inducted in the Colorado Women’s Hall of Fame.

Margaret Buckner Young (1921-2009), the artist’s grandmother, was a professor of educational psychology at Spelman College and children’s book author who served on the boards of the Metropolitan Museum of Art and Lincoln Center in the 1980s, when such representation was extremely rare for African Americans at major cultural institutions. She also supported Dance Theatre of Harlem and Harlem School of the Arts.

Casteel’s grandfather is Whitney M. Young Jr. (1921-1971). He was among the speakers at the 1963 March on Washington in his capacity as executive director of the National Urban League. Casteel was named for Vernon E. Jordan, who succeeded Young as leader of the civil rights organization.

On Instagram, Casteel said she was honored McIntosh made a portrait of her and thrilled with the outcome: “@waydemcintosh just got 3rd place in the Outwin Boochever Portrait Competition!! This is the painting he submitted and got the prize for!!! And it’s a painting he did of me!!! I’m so in wonder and gratitude for the knowledge, wisdom, friendship, and laughter this man has brought to my life. I am beyond lucky to call him a best friend y’all…”

Upholding a formidable family legacy, Casteel is garnering early acclaim for making portraits that document and uplift the community, portray dignity, and make visible the often unseen. “Jordan Casteel: Within Reach,” her first solo museum exhibition in New York, opens at the New Museum on Feb. 19.

Reflecting on his intent, McIntosh says: “In the painting, I think [Jordan’s] acknowledging her legacy but she’s also asserting herself as a dominant presence.” CT


“The Outwin 2019: American Portraiture Today” is on view at the Smithsonian’s National Portrait Gallery, Washington, D.C., Oct. 26, 2019-Aug. 30, 2020


PEOPLE’S CHOICE One of the 2019 finalists will receive the People’s Choice Award. The public can vote for their favorite portrait through April 24, 2020


A catalog is published to document each cycle of the portrait competition. Featuring Wayde McIntosh’s portrait of Jordan Casteel, the most recent edition, “The Outwin Boochever Portrait Competition 2019: American Portraiture Today,” is offered in the museum shop and will be available more widely later this year. “The Outwin Boochever Portrait Competition 2016: American Portraiture Today” features Amy Sherald’s first place portrait “Miss Everything (Unsuppressed Deliverance)” (2016) on the cover. “Jordan Casteel: Returning the Gaze” documents Jordan Casteel’s first major museum exhibition, which was organized by the Denver Art Museum, her hometown museum. Due in April, “Jordan Casteel: Within Reach” accompanies the artist’s forthcoming solo exhibition at the New Museum in New York.


Artist Wayde McIntosh discusses his portrait of Jordan Casteel, which tied for third prize in the National Portrait Gallery’s 2019 Outwin Boochever Portrait Competition. | Video by National Portrait Gallery


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