Based on Captain John Orr's previously unseen campaign diary and personal documents, this is the first biography of the man who would become Superintendent of the Scottish Naval & Military Academy (SNMA). We follow John during his eighteen months in Portugal and Spain informed by his first-hand accounts of the Battle of Salamanca, the siege of Burgos and fighting in the Pyrenees. Later he fought at Quatre Bras and was wounded at Waterloo. He was retired on full pension in 1821. Ten years later, aged 41, resigning himself that he would no longer be commissioned into a regiment, he enrolled as a captain in the Edinburgh Militia. Almost immediately he was asked to become the Superintendent of the Scottish Naval & Military Academy which was situated in Edinburgh. It had been established six years earlier and was struggling after the Directors had made a number of bad decisions.John's appointment stabilised the SNMA and the enrolment started to grow. He had enthusiasm for his job and managed to mix discipline with affection for the boys. In 1832 the Duke of Wellington became President. By the mid-1840s it had become a successful military college. It sent over a thousand young men into the services, including over a hundred who fought in the Crimean War. Nearly every British army regiment had at least one officer who had studied at the SNMA. Through John's letters, the history of the Academy is interwoven with a description of the Orr family. John died in 1879, aged 89 years old. He was the last surviving member of the Black Watch who had fought at Waterloo. The book is brought to life with paintings and photographs of John, his family, his uniform and pages from his Peninsular War diary. It is an intimate portrait of a soldier who served his country on and off the battle field.