NEW YORK, NY.- In one of the more surprising turns in his life, Toddrick Brockington, a felon for 26 years and now head of a mentoring program, will attend a gala where his portrait will be a major attraction.

The oil painting is part of the Art Show held by the nonprofit Art Dealers Association of America (ADAA) at the prestigious Park Avenue Armory on Manhattan’s Upper East Side. The show has been held for 35 years to raise money for the 130-year-old Henry Street Settlement, a community services organization for residents of the city’s Lower East Side.

The show, running Nov. 2 to Nov. 5, has always had an unusual uptown-downtown relationship, linking the increasingly unequal worlds within New York and in the country as a whole. This year the connection between the two worlds is underscored more than usual with paintings by Kate Capshaw, a former actress, who painted the portrait of Brockington.

A selection of 20 oil paintings in her series Unaccompanied — large portraits of young people experiencing homelessness — will also be shown at the Dale Jones Burch Neighborhood Center, a former fire station that is now part of the Henry Street Settlement. That show runs from Oct. 31 to Nov. 19.

This is the first time the Art Show has linked to an exhibition downtown; it will be free to the public, meaning “the community can connect and be part of it,” said David Garza, president and CEO of Henry Street Settlement.

Capshaw’s painting of Brockington will appear uptown at the Armory. The downtown show will include a painting by Capshaw of three brothers in Brockington’s program, which focuses on guiding and supporting boys and young men who are vulnerable and at risk of getting caught up in the criminal justice system.

The ADAA is a membership organization of about 200 fine art galleries nationwide. Henry Street Settlement serves about 50,000 people each year: half through its visual and performing arts classes free to those in public housing; and half through its social services helping the unhoused, the unemployed, those needing help to feed themselves and their families, and those struggling with mental health issues.

The relationship between the two institutions means that “while being a beacon of the glamour aspect of the city, it can help the real people of the city,” said Lisa Corinne Davis, one of the artists whose work will be exhibited at the Armory.

The amount raised by the Art Show for the Henry Street Settlement — about $1 million annually through its gala benefit and ticket proceeds — is the organization’s largest donation of discretionary money, giving it the ability to respond to crises as they occur, such as the COVID-19 pandemic or asylum-seekers, Garza said. Most of Henry Street Settlement’s funding comes from government agencies, earmarked for specific programs.

Capshaw, 69, who has been painting for about 15 years, started creating portraits in 2016 of homeless youth and those living on the edge in Los Angeles. Since then, she has traveled to other cities to paint young people as part of the series.

Each painting, 64 inches by 44 inches, portrays the subject staring directly at the viewer at eye level, mostly unsmiling, against a black background representing a lack of refuge.

“I think the night is when you really realize that you haven’t a shelter,” Capshaw said.

In 2019, three of the paintings were selected as finalists in the Smithsonian National Portrait Gallery’s juried show, the Outwin Boochever Portrait Competition, and were shown on a national tour.

Capshaw does not sell her work, but all the other pieces from the 78 galleries represented at the show will be on sale, priced from about $10,000 to $5 million, said Maureen Bray, the ADAA’s executive director. Tickets to the Art Show are $20 until Wednesday, then $30. Students are half-price at the door, and children under 12 are free.




Every ADAA member is invited to submit a proposal to the fair; half of those displayed are selected by all those members who submitted proposals and half by the Art Show committee, which is made up of members, Bray said.

Jameson Green, 31, an up-and-coming artist from Hudson, New York, was one of those chosen for the first time. His work, nightmarishly cartoonish and filled with symbols of the nation’s violent past — such as nooses — brings to mind the work of cartoonist Robert Crumb and is also influenced by German artist Max Beckmann.

One of his recent shows in Brussels was called “Mud Made Monsters,” a phrase from a song by one of his favorite rappers, Pusha T. “The characters in those paintings were very much going through their own trials, tribulations and developing as people and, in a lot of cases, some of the darker elements took the forefront,” Green said.

His creatures represent Green’s philosophy that “even in the best of us, we have the sides to us that are undeniably destructive. And they really can get out of hand if we don’t keep them in check.”

There is darkness but also wit. A sign in one of his paintings reads, “Colored Only,” but the world “Colored” is crossed out and replaced with POC.

“We relabel something with the idea of thinking that label will make things better,” he said. “However, the path still comes with its challenges that are unique to the people who are experiencing it.”

Davis, 65, a Brooklyn-based artist, is a first-time exhibitor at the show but a longtime attendee.

Her art, which is part of a number of private and public collections, including the Museum of Modern Art, the J. Paul Getty Museum and the Victoria and Albert Museum in London, takes issue with the modernist notion of the grid, which “stood for universality, for oneness,” she said.

“As an African American woman of light skin who went to a Quaker school and grew up in an Orthodox Jewish neighborhood, I don’t understand that notion of oneness. So I’ve always been tweaking with the idea of unity,” she said.

One way is to distort the grids, which are what the eight colorful paintings that she is showing in the Art Show do. They seem to lead the viewer in one direction, then veer off into another one.

People are always trying to find patterns in things and people, and too often, “those patterns are faulty — they don’t tell you the truth,” Davis said.

That thought leads back to Brockington, whose 53 years of life have taken many shapes and paths. He served 26 years in prison for homicide. Released in 2017, he often dropped by Henry Street Settlement’s Jobs Plus program looking for employment.

Then one day his employment counselor told him the Henry Street Settlement had received funds to create a position called “credible messenger,” mentoring and inspiring young people. Brockington created the Mentoring and Nurturing program about five years ago from his own lived experience.

The idea of being an invited guest at a gala where his portrait will be shown is one path he certainly did not expect. But he is more than good with it.

“One of the great things is knowing this portrait will be around long after I’m gone,” Brockington said. “If one person asks, ‘Who is this person?’ and my story is told, it might ignite the same fire I had within me to just go out and help people.”

This article originally appeared in The New York Times.