In 1943, Paisley went with the Eighth Army into Sicily and then into Italy. Whilst he was on active service in Italy he received the news that his younger brother Alan, aged fifteen, had died at home from scarlet fever and diphtheria. In June 1944, Paisley took part in the liberation of Rome and rode into the city on top of a tank, an event he recalled 33 years later when Liverpool won the 1977 European Cup Final in Rome's Stadio Olimpico. Paisley's regiment moved on to Florence where they encamped at ACF Fiorentina's Stadio Artemio Franchi. In Florence, Paisley saw boxing exhibitions by Joe Louis and Sugar Ray Robinson which generated another sporting interest and one for which he and Bill Shankly shared a passion while they worked together.