A trove of details has been sent to The Royal Gazette on the life of James Outerbridge, a Bermudian pilot in the Second World War shot dead at the age of 20 while attempting to escape a prisoner of war train in Italy.

The appeal for information came from Italian historian Daniele Celli, writing from the city of Rimini in an effort to find a face and story behind the plain military gravestone in the local military cemetery.

James was killed by a guard on May 1, 1943, as he attempted to slip away while the train paused.

Bermuda Legion caseworker Carol Everson speculated that the escape attempt could have been well-founded — although supposedly being transported to another prison camp, James and other POWs ran a grave risk of execution, she said.

Former Whitney Institute student J Hubert Jones recalled a painting of the late pilot prominently displayed on the wall at the front of the school’s assembly hall, when he started there in 1945. James’s brother, John Outerbridge, shared his class, and their mother, Ms Edith Urma Outerbridge, was “always proud to tell students her son died at war serving our country”.

“I suspect there are quite a few ‘Whitneyites’ living today that schooled with James or know more about him,” Mr Jones added.

Colin Pomeroy of Devon in the UK, author of the book The Flying Boats of Bermuda, wrote that Flight Officer Outerbridge had piloted a Vickers Wellington MkVIII torpedo bomber HX522 of No 458 Squadron of the Royal Australian Air Force, “which took off from Luqa, Malta, at approximately 2020 hours on March 24, 1943, but failed to return to base after ditching off the coast of Sicily after an engine failure”.

All the other crew, with the exception of James, returned safely to the UK at the end of the war, he added.

Mr Pomeroy continued: “He is buried at the Ravenna Commonwealth War Graves Commission Cemetery, north west of Rimini on the Italian Adriatic coast.

“The rest of the crew were Fg Off G Buchanan, Fg Off GWF Barnett, F Sgt DJ Tunney, Fg Off AC Main, and F Sgt JCO Wilson.”

JoEllen Outerbridge DeMarco, of Sarasota, Florida, recalled her first cousin, 13 years older than she, who had been away at school in the UK while she was growing up.

“I do remember when Aunt Enith received notice of his death and the family congregated at Dean Hall,” she recalled.

“Enith Outerbridge was my father, Earl Outerbridge’s sister. She had been married in New York but after her divorce and return to Bermuda she went back to her maiden name. Her grand nephew, Bill Outerbridge, who lives in Bermuda, visited Jimmie’s grave in Ravenna a year or so ago and as a memorial to his Bermuda roots left a jar of Outerbridge peppers, a bottle of Gosling’s rum and a Bermuda flag at his grave. He described the grave site as a beautiful, serene spot.”

Mr Outerbridge confirmed the story, saying he’d also “just received back a portrait of Jimmy from his cousin Barbara Faber who lives in Florida, which used to hang in Dean Hall, Smith’s, which was the family homestead”.