Cultural loss cited in Churchill portrait theft sentence appeal

Law360 Canada (November 7, 2025, 2:53 PM EST) --

John L. Hill

It was the Canadian equivalent of a break-in at the Louvre. It involved a photograph taken in 1941 during Winston Churchill’s visit to Ottawa, where then-prime minister Mackenzie King invited Yousuf Karsh to photograph the U.K. leader. After delivering a speech, Churchill entered the Speaker’s chamber, where Karsh was waiting with his lights and camera. Pressed for time with the British prime minister, Karsh plucked a freshly lit cigar from Churchill’s mouth just before taking the shot. The result was the U.K. prime minister posing with one hand on his hip and his brow furrowed into a deep scowl.

“I knew after I had taken it that it was an important picture, but I could hardly have dreamed that it would become one of the most widely reproduced images in the history of photography,” Karsh later wrote. In 2016, the scowling photo became the image that now appears on the British five-pound note. Karsh gifted the photo to Ottawa’s Château Laurier hotel.

Sometime in 2022, Jeffrey Wood stole the Roaring Lion portrait of Churchill from the hotel and replaced it with a forgery. The original was sold through a London auction house. The stolen item was later recovered and returned to public display with the assistance of international authorities.

Wood pleaded guilty to theft over $5,000, forgery and possession of stolen property for the purpose of trafficking, receiving a sentence of two years less a day (R. v. Wood, 2025 ONCJ 285).

The sentencing judge identified several aggravating factors, including the theft of a piece of major cultural and historical importance, the deliberate forging and trafficking for profit, and the damage caused to the artwork. Mitigating factors consisted of the appellant’s guilty plea, remorse, lack of prior convictions and the time spent under strict bail conditions. The judge indicated that without mitigation, a three-year prison sentence would have been appropriate.

On appeal, the appellant claimed that the judge erred by relying on foreign case law (United States v. Goldman, 953 F. (3d) 1213 (11th Cir. 2020); United States v. Medford, 194 F. (3d) 419 (3rd Cir. 1999); and a U.K. Appeal Court decision, R. v. Stanton [2013] EWCA Crim 1456), failing to consider a conditional sentence, overlooking his motive to help his brother, and misapplying the concept of “breach of trust.”

The Court of Appeal dismissed all grounds of appeal, affirming that the sentencing judge correctly relied on international cases for guidance due to the limited Canadian precedents, properly acknowledged the intangible cultural harm involved, and appropriately balanced the aggravating and mitigating factors. The reference to a “breach of trust” was metaphorical, referring to the public’s trust in preserving cultural property, not a legal breach under the Criminal Code.

The court concluded that the sentence was appropriate and proportionate, highlighting the importance of denunciation due to the cultural value of the stolen artwork.

Justice Patrick Monahan, with Justice William Hourigan concurring, granted leave to appeal but dismissed the sentence appeal.

Justice Jonathan Dawe advanced a well-reasoned dissent. He disagreed with Justice Monahan’s conclusion upholding the sentence and found that the sentencing judge made errors in principle that affected the outcome.

He concluded that the sentencing judge erred by limiting the analysis to art theft and forgery cases instead of considering the offence within the broader context of property crimes under the Criminal Code. The judge also incorrectly relied on the scarcity of Canadian art-theft cases as a reason to depend on foreign decisions without accounting for differences in sentencing regimes. This approach led the judge to overlook the principle of proportionality (s. 718.1 Criminal Code), which requires comparing the severity and moral blameworthiness of the offence to those of other Canadian property offences, not just art-related ones.

The sentencing judge relied on cases from the United States, the U.K. and New Zealand, where offenders received prison terms ranging from 3.5 to seven years, to support the imposition of a sentence within the penitentiary range. The dissenting justice argued that the judge used these cases not just as guidance but effectively as benchmarks for sentence length, despite the differing legal frameworks abroad.

While recognizing the cultural importance of the photograph, the dissent pointed out that the print’s market value was modest (insured for $20,000 and sold for less than $10,000). Similar Canadian cases involving much larger financial losses, such as fraud against vulnerable victims, had led to reformatory-style sentences rather than prison terms. Therefore, the cultural significance of the item did not elevate this theft to the highest level of property crimes.

The errors significantly affected the sentence, justifying appellate intervention under R. v. Lacasse, 2015 SCC 64. The dissent would have allowed the appeal and replaced it with a conditional sentence of two years less a day.

Justice Dawe stated that the statutory conditions for a conditional sentence under s. 742.1 of the Criminal Code were met; the appellant posed no risk to community safety; and a conditional sentence could still achieve denunciation and deterrence, primarily if structured to be longer or more restrictive than a custodial term, consistent with R. v. Proulx, 2000 SCC 5.

He would have allowed the appeal and replaced the sentence with a two-year less-a-day conditional sentence served in the community.

Following the delivery of the judgment, Canadian Press reported on Oct. 30, 2025, that Lawrence Greenspon, Wood’s lawyer, will seek leave to appeal to the Supreme Court of Canada in the coming weeks, based on reasons put forward by the dissenting judge.

Greenspon said Wood had turned himself in to jail as required, though he will be seeking bail pending the leave to appeal application.

John L. Hill practised and taught prison law until his retirement. He holds a JD from Queen’s and an LLM in constitutional law from Osgoode Hall. His most recent book, Acts of Darkness (Durvile & UpRoute Books), was released July 1. Hill is also the author of Pine Box Parole: Terry Fitzsimmons and the Quest to End Solitary Confinement (Durvile & UpRoute Books) and The Rest of the (True Crime) Story (AOS Publishing). Contact him at johnlornehill@hotmail.com.

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