10 Most Expensive World War II Items – Objects Owned By Hitler & Churchill

The Second World War is the biggest and hopefully the last global-scale conflict this world will ever see. That said, it was a historic moment that helped shape the modern world. Millions of lives were lost but history was made, hopefully for the better.

That said, artifacts from such a chaotic time have evolved from a commercial standpoint. Many items that survived World War II may have been worth nothing during the time, but now carry heavy price tags that only people with lots of money to splurge can only afford. It looks like a lot of people want a piece of history, even if its past is filled with horror, fear, and agony.

World War II may have been a time of misery and pain, but it was a phase that taught humanity about hope, courage, and bravery. We all want to have something like that, don’t we? Here are the top 10 most expensive World War II collectibles ever sold.

#10 Winston Churchill’s Snuff Box: $24,000


A snuff box is a small ornamented container that holds snuffs, or basically scented powdered tobacco. Churchill gave his personal silver snuff box to the doorkeeper of the House of Commons after he lost his during the Germans’ blitzkrieg attack on London. In 2006, this snuff box was auctioned by Sotheby’s in July 2006.

#9 Churchill’s Typescript: $37,000


This particular item is a typescript detailing a message from Churchill following the invasion of Sicily and the ouster of Mussolini. It also includes several corrections from the man himself. This typescript was auctioned by Sotheby’s for nearly $37,000 back in 2003. (Image shown is not the actual item described)

#8 Peter White’s Archive: $50,000


Peter White was an infantry platoon leader who served in Scotland’s Royal Army. During the war, he documented the daily events which date from January 1st, 1938 to August 10th, 1944. He placed all his recollections of the war in a diary, which also included drawings, sketches, and several news clippings. Also sold with the manuscript were 4 medals, a Kodak camera, and photos processed from the film of the said camera.

#7 Mussolini’s Order of Courage Medal: $123,000


When Benito Mussolini was dismissed by his administration and subsequently arrested in 1943, his possessions were also taken, among which was his Order of Courage medal. The medal survived the war and was auctioned by La Galerie Numismatique in March, 2012 for $123,000. The sale indicated the growing interest of World War II collectors in items once owned by the Italian dictator.

#6 Hitler’s ‘Night Guard’ Luger Pistol: $161,000


It is a known fact that Adolf Hitler was always on his toes when it comes to his safety. So much that his “Night Guards” were issued rare Luger pistols loaded with tracer bullets and fitted with flashlights to keep him safe at night. One of the Lugers survived and surfaced in 2012 at a Rock Island auction. The handgun was sold for a whopping $161,000.

#5 Anne Frank’s Letters: $166,000


While Anne Frank is more known for her diary, which was found after the war, other written works she made also bagged a lot of money. Prior to the invasion of The Netherlands in 1940, Anne Frank and her sister had been corresponding to their pen pals based in Danville, Iowa. The letters managed to survive the years. The memorabilia of Anne Frank include two letters, a postcard, and two passport-size photographs. The letters were authenticated by the director of the Anne Frank Center in Amsterdam. Swann Galleries got hold of the letters and auctioned them for $166,000.

#4 Enigma Cipher Machine: $221,000


The Enigma Cipher machine helped the Allies a big deal in turning the tide of war against the Germans. This spy machine cased inside a wooden box helped the Allies decode secret messages of the German military, which exposed their troop movements, orders, strategies, and other vital information. This particular Enigma Machine was sold by Christies in September, 2011 and reported to be in perfect working condition.

#3 Hitler’s Ceremonial Brass Writing Desk: $422,000


This is practically the desk on which Adolf Hitler signed the Munich Pact, the agreement that would lead to World War II. Engraved on the desk are Hitler’s initials AH and it is fitted with an inkwell. The desk is also adorned with the Nazi’s crest of an Eagle and Swastika. 2nd Lieutenant Jack McConn confiscated the desk from Hitler’s Munich office in 1945 and the piece of furniture soon surfaced at an auction by Alexander Autographs in December, 2011. (Image shown is not the actual desk described in this entry.)

#2 Victoria Cross Medal: $555,000


Sometimes, it is the little known fella who puts himself in great danger to achieve victory. That is the case for Private Edward Kenna of the Australian 2/4th Battalion, who exposed himself to the risk of getting killed just to take out a Japanese machine gun position during a battle near Wewak, New Guinea in 1945. Despite heavy machine gun fire, Pvt. Kenna killed the machine gun crew and was awarded the Victoria Cross Medal. The medal was soon auctioned by Spink & Son in July, 2011

#1 Hitler’s Mercedes Benz 770k: $10 Million


This is the car that chauffeured Adolf Hitler through the hordes of adoring Germans and Nazi supporters before and during World War II. Tracking the classic automobile required careful research and patience. The car was finally identified as Hitler’s after a very thorough study of historical snapshots that linked the German leader to the vehicle. Soon after, German car dealer Michael Frohlich sold the Mercedes Benz to a Russian billionaire.

Allan Jay

By Allan Jay

Allan Jay is FinancesOnline’s resident B2B expert with over a decade of experience in the SaaS space. He has worked with vendors primarily as a consultant in the UX analysis and design stages, lending to his reviews a strong user-centric angle. A management professional by training, he adds the business perspective to software development. He likes validating a product against workflows and business goals, two metrics, he believes, by which software is ultimately measured.


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