Though long-established and well-documented the Swintons never came to hold as much land or as much power as some other Border families. Nevertheless they have included many distinguished men. Among them was Sir John Swinton, one of the few Scots recorded as having fought on the English side in the Hundred Years’ War. He made an interesting agreement with John of Gaunt, Duke of Lancaster, which included the following among other terms:

Sir John fully justified the trust placed in him, through his conduct in a series of campaigns and particularly at Noyon (between Amiens and Paris) when he fought his way single-handed into the town. About this time, he married a young wife, Joan, who died without children and whose jewels were stolen by Alice Perrers, Edward III’s mistress (who also stole the King’s rings from his fingers as he lay dying). He appealed to the King for their return, but they could not be traced, and it is not altogether surprising that he returned to Scotland soon after. He was one of the Scottish leaders at Otterburn (1388) and married twice more, his second wife being Margaret, Countess of Mar, while his third wife was Margaret Stewart, granddaughter (or some say daughter) of Robert II. He was killed at Homildon Hill (often confused with Halidon Hill, where the first of the Turnbulls died), leading no more than a hundred Scots against the massed ranks of the English archers. The Scots were drawn up in schiltroms, a "hedgehog" formation also used by the Ancient Greeks (who called it the phalanx) and by the Swiss, more or less invulnerable to ordinary infantry but highly vulnerable to archers. Swinton urged them not to "stand like deer to be shot, instead of indulging your ancient courage, and meeting your enemies hand to hand. Let those who will descend with me, that we may gain victory, or fall like men". He was of course right; the only way to cope with the archers was to meet them head-on and accept the necessary casualties in order to break them — for they would have been helpless at close quarters against the massive Scottish spears — but few of the Scots were personally prepared to be among the "necessary casualties". Among those few was a young man, Adam Gordon, who had a long-standing feud with him. Gordon fell on his knees before Swinton, begging for his forgiveness and for the honour of knighthood before they went down to die together. Sir John knighted him on the spot and they led their small body of men down to their inevitable but heroic end.

His son, also Sir John Swinton, fought on the French side in the Hundred Years’ War. At the battle of Baugé (1421) he disabled the Duke of Clarence, brother of Henry V and commander of the English army:

Clarence was then killed, some say by the Earl of Buchan, who led the Scots, though others give the honour to Alexander MacCausland. Sir John was himself killed, along with Buchan, at the battle of Verneuil a few years later; the English commander on this occasion being another of Henry V’s brothers, the Duke of Bedford, Verneuil was, however, the last major English victory; the tide turned decisively in favour of France at Orleans a few years later (again with many Scots involved) and the English who, together with their Burgundian allies had at one time held two-thirds of the country, then lost everything except Calais in the remaining 24 years of the war.

In the seventeenth century, one of the most remarkable members of the family was John Swinton of Swinton, who was originally on the King’s side in the Civil War, but went over to Cromwell in December 1650, possibly after having been captured by English soldiers. He served as a member of the Council of State for Scotland and as a Commissioner for Justice. After the Restoration he was tried for treason; his life was spared but he was imprisoned for some years, and his lands were forfeited to the King and granted to the Earl (later Duke) of Lauderdale. They were restored to his younger son in 1690. This son, Sir John Swinton, was a merchant in London and Holland a founder of the Bank of Scotland as well as a laird and a member of the Scottish Parliament before the Union and of the first UK Parliament thereafter.