Some wartime stories are preserved in medals. Others survive in logbooks, photographs, papers and personal mementoes, each adding detail to a life shaped by service. The medal group and archive of RAF Flying Officer Leslie Valentine DFC CdeG does both, bringing together decorations, documentation and first-hand records from one of the most remarkable low-level flying missions of the Second World War. We are proud to present the collection as lot 3139 in our Militaria, Medals & Sporting Guns auction ending 1 October. 

Valentine was the pilot of Douglas Boston “E Easy” on D-Day, 6 June 1944, when he flew at just 50 feet above the Normandy beaches to lay smoke and help shield Allied invasion forces from enemy fire. The International Bomber Command Centre records that Valentine later described the experience as flying “through the gates of hell”.

Highland Light Infantry & The RAF

In 1939, Leslie Valentine was called up for military service and joined the Highland Light Infantry, spending ten months in France before returning to Britain. He later volunteered for RAF aircrew, beginning a new chapter that would take him from infantry service to pilot training.
Valentine trained at Medicine Hat in Alberta, Canada, before returning to Britain for operational training at RAF Bicester and RAF Finmere, where he learned to fly Blenheim and Boston bombers. His first flying logbook, now also recorded by the International Bomber Command Centre, documents his training between October 1941 and August 1943, with stations including RAF Theale, Clyffe Pypard, Medicine Hat, Shawbury, Stradishall, Bicester and Lyneham.

By 1944, Valentine had been posted to No. 88 Squadron, 2nd Tactical Air Force, Bomber Command. The squadron’s operations were mainly flown in daylight and close formation, targeting roads, railway yards, bridges, transport routes and other key supply lines as Allied forces worked to disrupt German reinforcements.

The D-Day Mission

The defining moment of Valentine’s wartime service came on D-Day, when his Boston aircraft was tasked with laying smoke to protect invading troops. The accompanying logbook in this archive includes the entry for 6 June: “Ops ‘D’ Day smoke laying to cover invading troops off Le Havre.” The mission demanded exceptional nerve and precision. Valentine flew low over the invasion area at around 50 feet, releasing smoke canisters while exposed to fire and confusion from the battle below. Contemporary reporting in The Independent records that he had only 46 seconds to release four smoke canisters while flying at 250mph, with German guns firing from inland and Allied forces on the ground unsure of the identity of aircraft flying so low overhead.

Two aircraft were lost during the mission, but Valentine returned safely. His role in the D-Day smoke-laying operation became one of the most powerful episodes in his story, later captured by aviation artist Michael Turner in the print Friendly Smoke, D-Day 6th June 1944. The lot includes a copy of this print, signed by Valentine and Flight Lieutenant John Mackenzie, together with a personal note from the artist.

Medals & Memories

The Valentine’s D-Day flight was only one part of an exceptional operational record. He flew 60 missions with 88 Squadron, including 53 daylight and seven night operations, with targets across France, Belgium, the Netherlands and Germany.

The archive brings that service into focus through the Distinguished Flying Cross medal group, campaign medals, the Croix de Guerre with Silver Star, two logbooks, Boston IV pilot’s notes, photographs, paperwork and the signed Friendly Smoke print. Also included is a separate cased Defence Medal, presented to Valentine by David Cameron at Downing Street in 2012, recognising his earlier service with the Highland Light Infantry before he joined the RAF.

Together, the medals and papers form a powerful record of a pilot whose wartime service stretched from infantry duty to one of the most hazardous low-level missions of D-Day.

A Story Preserved

Leslie Valentine’s story belongs to the wider history of D-Day, Bomber Command and the tactical air war over Europe, but it is also intensely personal. It is the story of a man who began the war in the Highland Light Infantry, retrained as a pilot, flew daylight operations in close formation and on 6 June 1944 took his Boston down to extraordinary low level to protect men landing on the beaches below.

This medal group and archive offer collectors far more than a set of decorations. They preserve the paper trail, visual record and personal context of a remarkable RAF career, including one of the most hazardous and memorable missions of D-Day. The group will be offered in our forthcoming Militaria, Medals & Sporting Guns Auction. 

Browse the catalogue for further details and contact our specialists for condition reports or bidding information.

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