Jack was captured in Libya on 8 April 1941. He was transferred to Italy and spent two years in various camps. At first, in PG 17 Rezzanello, then PG 41 Montalbo, and finally PG 49 Fontanellato. He escaped on 8 September 1943.

On 11 September, following an order from Lt. Col. Hugo de Burgh,, the PoWs left the camp in groups. Around 1 pm, the evacuation was completed, and the Germans arrived roughly two hours later. The escapees spent the night on the banks of the Rovacchia stream (Bund), a few kilometres from the camp. However, it was soon apparent that keeping together some 600 men was impossible. They thus decided to split the group into smaller parties. Some former PoWs, including Jack, volunteered to work on one of the nearby farms, but this arrangement did not satisfy him or his companion,   Costas Jacovides, a Cypriot.

The two approached Bianca Galati in Fontanellato (Parma), who had previously brought them food and were welcomed in her house for a few days.

However, for security reasons, they soon moved in the following weeks to a farm in Cannetolo (Parma), belonging to the Gotti family. Meanwhile, the German offered a reward to whoever could bring them an escaped PoW and threatened harsh penalties for whoever sheltered one.  «In spite of these notices, the Italians did not, as far as I know, give up any prisoners». 

Jack and Costas stayed in Cannerolo from 16 to 27 September, helping on the farm. Their conditions were good: they were fed and slept in a comfortable bed. Their hosts nicknamed them Gianni (Jack) and Mario (Costas).

On 20 September, however, the Germans started combing through the area, catching many PoWs in the farmhouses that were housing them. Thus, Jack and Costas were forced to make a decision: 

Costas decided to stay while Jack left. He departed with Marcus Kane Burman of the African Medical Corps, the dentist at the Fontanellato PoW camp, and his aid, A.B. McLean. The three companions left Cannetolo at 5 am on 28 September 1943, heading north to cross the Swiss border. They crossed the Via Emilia without many problems and reached Costamezzana (Parma), where they were welcomed by a family who let them dry their clothes, drenched in the rain, and sleep in the stable. Every day, they moved to a different locality. Near Pellegrino Parmense, they met David Eraskine, John Dean and Gaston Vian, all from Fontanellato, who were also travelling toward Switzerland.

At the end of the week, they arrived in Morfasso (Piacenza), and here they decided to change their destination. Their objective became reaching the Allied front line in the south rather than crossing into Switzerland.

Their journey southward started on 2 October and, although regretful to retrace  their steps, they felt it was the right choice. In the following days, they crossed the river Ceno and reached Péssola (Parma), where they were invited into the priest’s house to listen to the nine o’clock news. Unfortunately, the news was not reassuring, as the Allies were advancing rather slowly.

During their journey, they always found a family willing to help them, providing them with food and shelter, often in exchange for dental work.

On Saturday, 9 October, they reached Gazzano (Reggio Emilia) with four other former PoWs who had escaped from Fontanellato. They stopped there a few days to rest and resupply.

On 12 October, they climbed the Appennines, guided by a family (with two mules) who was returning home for the winter. Their journey along the Apennines, now covered in snow, lasted 38 days. In November, the three reached Villa Santa Maria (Chieti), where they met two escapees from Fontanellato. Together, they headed towards Frattura (district of Sanno, L’Aquila). The village was on the hills above the Sangro river, from which they could see the Allied troops below.

On 19 November, while they were approaching the frontline, Jack and his two companions were intercepted and captured by a German patrol. During the following days, they were transferred to Lazio, near Frosinone. On 30 November, they were loaded onto a train heading to Germany. Jack, with many other PoWs, decided he wanted to escape:

Florence, however, was 233 kilometres away. The two escapees found refuge in a Franciscan monastery, where they remained for a few days. Later, they reached Santa Brigida, near Pontassieve, where Laing had been welcomed during his journey south before being recaptured.

On 21 December, they were in Florence, guests of an industrialist family, Valvona-Buti, who had already assisted more than 14 escaped PoWs. They spent two months in their house. In January, equipped with fake documents, Jack and Anthony left Florence to reach Venice, escorted by a Communist, Angelo Salvatore. They aimed to cross the Yugoslavian border, contact the Slovene partisans and cross the Adriatic with a boat. The plan, however, did not come to fruition, and they were forced to return to Florence.

On 21 February 1945, they were involved in a new escape plan, this time toward Switzerland. They reached Milan and then left for Laveno, on  Lake Maggiore. They crossed the lake by ferry and went to Cannobio, on the other side. Their instructions were to knock on a coffee house’s door and give the owner a password. He would bring them on a path to Scraggio, where they would meet their guides. The two left at 5 am on 24 February 1945 and reached the top of the mountain around noon. Then, they finally crossed the border and entered Switzerland.

Jack’s journey lasted 168 days (his companions Marcus Kane and McLean also managed to escape and reach Switzerland) and encompassed 44 localities. After the war, Jack received a Mention in Despatches for his bravery during his escape, while Marcus Kane Burman was awarded the MBE for providing healthcare to his fellow PoWs.