Portrait Of The Mayoral Artist As A Spirit-Seeker

Stop to examine City Hall’s new portrait of John DeStefano and you may find your ego dropping away momentarily, allowing you to connect with not just New Haven’s longest-serving mayor but, through beauty, God. If Gerald York has anything to say about it.

That’s the goal of New Haven’s York, who painted the portrait. That’s why he paints pictures. That’s the approach he took to painting DeStefano’s portrait over the past six months.

The new portrait of New Haven’s outgoing two-decade incumbent mayor was officially unveiled in City Hall at 4 p.m. Thursday. It took a place alongside many other portraits of New Haven’s former mayors. The boisterous and nostalgic ceremony doubled as reunion of the many mayoral staffers who have worked under DeStefano in his 20 years in office.

Earlier in the afternoon, York was in his second-floor Erector Square studio, gathering together supplies for the unveiling. Wearing a tan coat over a dark suit, the 54-year-old painter sat to discuss his process, leaping up occasionally to make his points with the help of some of his paintings and drawings and sculptures.

“The whole reason I work is that I want people to have an experience of beauty,” York said. That experience can be transformational, spiritual, he said.

“For example, this drawing,” York said, standing up to point out a charcoal drawing he made of a woman’s head. A viewer who pauses before the drawing, a receptive viewer, may experience ​“a momentary lapse, where the ego drops off.” That release opens into a kind of ​“oneness, a connection with essence,” York said.

“I want people to remember their essence, their connection to the ground of being,” York said.

While the viewing of a portrait can be an opportunity for the viewer to drop the ego, for the subject of the painting, it can be a chance to inflate the ego. Asked about this, York pulled out a book of Diego Velazquez paintings. He pointed to the cover — an image of Juan de Pareja, painted around 1650.

Pareja wasn’t a nobleman; he was a painter who worked under Velazquez. The master painted Pareja as a warm-up to a painting of the Pope. The painting wasn’t meant to aggrandize Pareja, to present him as anything other than himself.

“If you stand in front of this painting,” York said, ​“time drops off between you and him. You can see the dignity in the man. This is life itself. That’s where God is.”

While York refers to the history of art, he also questions it. After speaking about Velazquez, he jumped up and pointed to a picture of another historical painting: John Singer Sargent’s Lady Agnew of Lochnaw. The 1893 portrait depicts Agnew draped over an armchair, leveling a sultry stare at the viewer.

Next to it on the wall hung York’s portrait of Kerry Alys Robinson, the head of the National Leadership Roundtable on Church Management — an executive, like many of York’s clients. Robinson sits up in her armchair, shoulders square to the viewer, wearing a suit.

“I was updating that motif,” York said. He called the Robinson portrait a modern version of the Agnew portrait, showing a strong modern woman.

York has been making portraits since the first grade. As an undergraduate at Yale in the late ​‘70s, he studied architecture. It was a compromise between practicality and artistry, since he was initially too nervous about earning a living to go for a career in art.

After graduation, he worked as an architect for several years. It never felt right. ​“I wanted something more personal, less technical,” he said. ​“It just wasn’t me.”

“That’s where faith comes in,” he said. ​“It’s so daunting to take that first step.”

Eventually, a ​“miracle” struck. York suddenly got a commission to go to Italy to carve a marble portrait of a wealthy benefactor to Michigan University.

“As I say, God,” York said. ​“The only way to put a life like mine together is if some kind of miracle happens over and over again.”

He quit his architecture job and flew to Italy.

York now works full-time as a portraitist. He said each painting takes him about six months.

York’s first step is learning about his subject, and working on preparatory sketches, to arrive at the composition. That can take a month, he said.

In the process, York learns about his subject’s character, values, and motivations, all of which informs the final painting. ​“There’s always an unfoldment of who the person is,” York said.

It’s a matter of reaching the real person, stripped of a public persona, York said.

In the case of the mayor, York learned that the DeStefano contains seemingly opposing elements in his character.

“The mayor is a very strong man,” York said. DeStefano has been willing to take a stand on difficult issues, on principle, York said. He mentioned the residency card battle, when DeStefano issued ID cards to all city residents, regardless of immigration status; and DeStefano’s hand in the creation of the START community bank, when he took on a larger regional bank.

So the composition had to show that strength and forcefulness, York said. He said he and DeStefano settled on an oak desk for the background of the painting, which ​“has a certain strength to it.”

“At the same time, John has a very receptive side to him,” York said. DeStefano is not ​“overbearing” or ​“dogmatic,” York said. That side of the mayor needed to come through in the composition.

York posed the mayor half-sitting on the desk, his arms relaxed, lightly holding his reading glasses. ​“Like someone’s coming into his office to talk to him,” York said. ​“It’s a balanced pose. He’s waiting to hear everything you have to say.

Early on, York did a full-size pencil study to finalize the composition. Then came a smaller oil study, to get the colors right, to ​“balance the color scheme.”

“You want to have warm against cool, light against dark,” York said.

York painted the mayor during eight sittings of two hours each. He focused on the mayor’s face during those sittings. He had a mannequin outfitted with the mayor’s suit, to work on depicting the mayor’s torso when the mayor wasn’t sitting for him.

During the sittings, York focused on representing the mayor’s features, but he also worked on finding the right facial expression.

“I try to establish a rapport by trying to make a connection with him on a human plan, so that the genuine side of him comes out,” York said. It’s clear when he’s arrived there, when he’s reached that genuine part of his subject, he said. ​“It kind of just rings.”

York’s portrait will now take a place on wall of City Hall, where portraits of all of New Haven’s other former mayors also hang. All the way back to Roger Sherman.