Yousuf Karsh's famous black and white 1941 portrait of Winston Churchill shows the British prime minister scowling directly at the camera, with one hand on his waist and the other resting on the head of a cane. It is the scowl to end all scowls, designed to reduce offenders to a gibbering mess.

What you see: A vintage gelatin silver print of a portrait of Winston Churchill, taken by Yousuf Karsh in 1941 and printed in the 1940s or 1950s. Heritage Auctions estimates it at $3,000 to $5,000.

The expert: Nigel Russell, photographs director at Heritage.

I wanted to start by talking about how this photo came about. Could you tell the story of how Karsh got this image? He set up a studio in Ottawa in the early 1930s. He was friendly with the Canadian prime minister Mackenzie King. He had a reputation in Canada, but he wasn’t that well-known. Churchill was doing a tour during World War II. He came to Washington and then Ottawa to get support for the war. He gave an electrifying speech in Ottawa. The Canadian Prime Minister asked Karsh to take a picture of Churchill, but apparently, no one told Churchill he was going to have his picture taken. He was annoyed to begin with. He lit a cigar, puffed away, and said, “OK, you can quickly take the picture,” very angrily. Karsh held out an ashtray [so Churchill could] take the cigar out of his mouth. He didn’t. He ignored him. Karsh made his final settings [on his camera] and just before taking the picture, he said, “Excuse me, Sir,” and took the cigar out of his mouth. That’s why you get a scowling look in the picture.

This image made Karsh’s reputation. How soon did he know the strength of what he had? When he took the photo, he knew it was good and important, but he didn’t know how important it would be. He went from a Canadian photographer to an international photographer. It launched his career of photographing heads of state and important people around the world.

I was thinking about that act–plucking the cigar from Winston Churchill’s mouth–and I’m not sure I’d be brave enough to do it… Karsh was a rather small man, and Churchill was an imposing figure who wasn’t paying any attention to him. He felt the need to get his attention and probably felt he didn’t have much to lose. He was not a very important photographer at the time, so he just did it. There is another photo that’s not very well-known because it’s just not the same, where Churchill is smiling. I think Churchill was actually impressed with what Karsh did, and let him take another picture.

When I think of Winston Churchill, I think of this photo. That’s the image that winks into my head. What makes it so effective? It’s exactly the way you picture him giving powerful speeches in World War II–a powerful, no-nonsense person. It’s one of those few instances where the portrait is what you imagine the personality of the person [to be] and conveys something more than a plain portrait. It makes you feel you have an idea that you can understand the person better.

How is the image a testament to Karsh’s talent? A couple of things make Karsh the most important portrait photographer of the mid-20th century. From a technical point of view, he was excellent–impeccable technique, fantastic lighting, print quality, all of that. The Churchill portrait marked a turning point. From then on, he’d try to get the subject to make a unique expression that shows their inner power, or shoot them in such a way that you wouldn’t normally see.

We know he took the photo in 1941, but I don’t see anything about the date when he printed this one. Can we pin that down? We don’t know exactly when he printed this particular one, but we are listing it as a vintage print. It’s an early print. Karsh did early prints at different sizes, 8 1/2 by 11 inches or 11 by 14 inches. We know it was early because he signed it in white ink, which he seemed to stop doing sometime in the 1950s. It has silver mirroring, which a photograph doesn’t get unless it’s quite old. It’s an oxidation of the silver in the print. If you hold it at an angle, there’s a silvery sheen to the darker areas of the print. Usually it takes 50 years or so to show up. Another indication of age is the print is warm in tone. It’s printed on cream paper, where later prints were on white paper.

The secondary market for photographs didn’t evolve until the 1970s. For whom would Karsh have made this gelatin silver print of his Churchill portrait? I think you have to look at it a little differently. Though the fine art photography market wasn’t created until the 1970s, there was a market for portraits of statesmen and celebrities. People would buy a portrait of someone they admired and hang it in their study. Karsh didn’t make a huge amount of money [from these prints] but you see early prints of Einstein, Charles De Gaulle, Dwight Eisenhower… even though the market for fine art photography didn’t exist, there was a market for this kind of portraiture earlier.

And it was not part of a limited edition? Right. Not until you get to the 1970s, to the fine art market, does he start making larger sizes and start doing editions.

How often does this pre-1970s print show up in auction records? I did a search in general of all different Karsh Churchill prints. There have been 187 up for auction since 1987, so about five or six a year, of which maybe one is vintage, or maybe less than that. [Standard reminder: 187 auction results doesn’t mean 187 individual prints went to auction. Some might have been the same print, consigned twice or more.]

And to be clear–because there was demand for portraits of statesmen before the 1970s, there would be more vintage prints of Karsh’s Churchill portrait floating around than you’d get for other types of vintage prints. Yes. I would say from a vintage point of view it’s fairly popular.

How involved would Karsh have been in physically making the print? From what I’ve read, he printed in the darkroom with assistants. He might have been supervising. It’s not clear if he handmade each print himself or if he told his assistants what to do. He was certainly not like some photographers who let their assistants do [the work] and never entered the darkroom. He was very much hands-on.

Is the world auction record for a Karsh photograph a Churchill photograph? And if so, what is it? It’s interesting. I did a search and it turns out the auction record for any Karsh is this image, and it was set at a Beijing auction house by a vintage 8 by 10 in 2015. That was kind of the peak of the Chinese art market auctions. It sold for $39,713. The next-highest result is for a vintage 16 by 20. It’s unusual because he didn’t [normally] make vintage prints that big. It would have been a special order in that size. It sold at Sotheby’s in 2008 for $20,000. Later on, once the photography art market got going, he made 16 by 20s and 20 by 24s.

Of all the collectible photographs of Churchill, is this the one that collectors want most? Oh yeah, by far. If someone’s looking for a Churchill portrait by any photographer, they gravitate toward this one. It’s one of the few where we do have crossover appeal to people who collect Churchilliana, people who collect World War II in general, and people who want a nice Churchill portrait.

Do collectors care if the portrait is vintage or not? A lot of the people who want this picture like it in the later, larger size. We sold a 20 by 24 for $11,300.

What condition is the print in? Silver mirroring is noticeable at an angle, and there are a few small spots of retouching. It’s in overall good condition.

How many Karsh Churchill portraits have you had at Heritage? In all, we’ve sold 11 since we’ve been having photograph auctions [the house began holding them in 2004]. Of those, three were vintage.

As we speak I’m looking at a digital version of the print. What is it like in person? Again, it gets into the realm of connoisseurship. Later black and white prints reproduce fine digitally. They’re what you kind of expect. With vintage prints, there’s a color to them, a warmth to them. The paper often has a bit of texture to it that you can’t see [in a digital reproduction]. It’s really nice to see them in person. They have a certain presence that you don’t get in later prints.

How to bid: The vintage print of Yousuf Karsh’s 1941 portrait of Winston Churchill is lot #73197 in the Photographs Signature Auction at Heritage Auctions in New York on April 6, 2019.

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