Simon (IV) Preston of Craigmillar

Simon (IV) Preston was a Scottish Nobleman, Provost of Edinburgh, and a close friend of Mary, Queen of Scots, who played a significant role in 16th century Scottish politics. He was born around 1510 at Craigmillar Castle and was the eldest son of George Preston and Isobella Hoppringill.

Early in his career, Simon held political office. He served as Bailie of Edinburgh by 1538 and as Provost of Edinburgh from 1538 to 1543, then again from 1544 to 1545.

Before June 5th, 1543, Simon married Jonet Betoun, the daughter of John Betoun of Creich. By November 16th of that same year, however, the marriage ended in divorce. They had no children.

In May of 1544, during the Rough Wooing, the English invaded Scotland and, after burning Edinburgh, attacked Craigmillar Castle. The castle soon surrendered; Simon Preston, taken prisoner, was marched to London and later released. Once free, Simon restored Craigmillar Castle, adding domestic ranges in the courtyard.

Simon married a second time, sometime after February 7th, 1549, to Elisabeth Menteith, daughter of William Menteith of Wester Kerse. They had at least five children: David, Simon, Marion, Margaret, and Helen.

Simon continued his public service in the years that followed. In 1554, he provided lead for repairs on Holyrood Palace. Three years later, he served as keeper of Tantallon Castle in 1557.

In 1561, Simon joined Mary, Queen of Scots, in her retinue upon her return to Scotland from France. He subsequently served on the Privy Council of Scotland and was reappointed Provost of Edinburgh from 1565 to 1568. During these years, Mary also named him Captain of Dunbar Castle. As Provost, Simon oversaw artillery provisioning and managed tax collection for the baptism of Prince James in 1566. In 1567, he gifted a building complex in Edinburgh for use as a hospital for the poor.

For three weeks in November 1566, Mary, Queen of Scots, stayed at Craigmillar Castle to recover from illness and rest. During her stay, her advisors, including the Earls of Argyll, Bothwell, and Huntly, devised the plan to murder her husband, Henry, Earl of Darnley. This plot became known as the "Craigmillar Bond." The intent was for Darnley to stay at Craigmillar on his return to Edinburgh; however, he did not care for Simon Preston and instead stayed at Kirk o'Field, where he was murdered on February 10th, 1567.

Throughout his life, Simon remained loyal to Queen Mary. However, after her defeat at Langside on May 13th, 1568, he signed a bond with William Kirkcaldy of Grange to defend the young James VI and Regent Moray.

Simon Preston died sometime between 1570 and 1575. His eldest son, David, succeeded him in the barony of Craigmillar.