[citation needed] Churchill was born in Colombo, British Ceylon,[1] to Alec Fleming Churchill (1876–1961), later of Hove, East Sussex, and Elinor Elizabeth, daughter of John Alexander Bond Bell, of Kelnahard, County Cavan, Ireland, and of Dimbula, Ceylon.

Alec, of a family long settled at Deddington, Oxfordshire, had been District Engineer in the Ceylon Civil Service, in which his father, John Fleming Churchill (1829–1894), had also served.

[1][3] Soon after Jack's birth, the family returned to Dormansland, Surrey, where his younger brother, Thomas Bell Lindsay Churchill (1907–1990), was born.

[10][11] Churchill left the army in 1936 and worked as a newspaper editor in Nairobi, Kenya, and as a male model.

[15][11] Churchill resumed his commission after Nazi Germany invaded Poland in September 1939 and was assigned to the Manchester Regiment, which was sent to France in the British Expeditionary Force.

On one occasion, to a general who had commented on his weaponry, Churchill is said to have replied "Any officer who goes into action without his sword is improperly dressed.

Jack's younger brother, Thomas Churchill, also served with and led a commando brigade during the war.

[20]: 41  As the ramps fell on the first landing craft, he leapt forward from his position playing "March of the Cameron Men"[21] on his bagpipes, before throwing a grenade and charging into battle.

[22] Churchill later walked back to the town to retrieve his sword, which he had lost in hand-to-hand combat with the German regiment.

[5] As part of Maclean Mission (Macmis), in 1944, he led the Commandos in Yugoslavia to support Josip Broz Tito's Partisans from the Adriatic island of Vis.

The landing was unopposed, but on seeing the gun emplacements from which they later encountered German fire, the Partisans decided to defer the attack until the following day.

Afterwards, he was transferred to a special compound for "prominent" POWs, including some actual or suspected relatives of Winston Churchill – within the grounds of Sachsenhausen concentration camp.

In late April 1945, Churchill and about 140 other prominent concentration camp inmates were transferred to Tyrol and guarded by SS troops.

A German army unit commanded by Captain Wichard von Alvensleben moved in to protect the prisoners.

[23] The prisoners were released, and after the departure of the Germans, Churchill walked 150 kilometres (93 mi) to Verona, Italy, where he met an American armoured unit.

Churchill, one of the first men on the scene, banged on a bus and offered to evacuate members of the convoy in an APC despite the British military orders to keep out of the fight.

Of the experience, he said: "About one hundred and fifty insurgents, armed with weapons varying from blunder-busses and old flintlocks to modern Sten and Bren guns, took cover behind a cactus patch in the grounds of the American Colony....

][26] After the massacre, he coordinated the evacuation of 700 Jewish doctors, students and patients from the Hadassah hospital on the Hebrew University campus on Mount Scopus in Jerusalem, where the convoy had been headed.

He also enjoyed sailing coal-fired ships on the Thames between Richmond and Oxford,[27] as well as making radio-controlled model warships.