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Olave Sinclair was probably a close relative of Edward Sinclair of Strome, who was foud of Shetland in the 1530s.John H. Ballantyne & Brian Smith, Shetland Documents, 1195-1579 (Lerwick, 1999), p. 39 no. 55.
Sinclair was involved in the murder of a William Lewis or Lowis and his three servants on Shetland in the silence of night in June 1543.John H. Ballantyne & Brian Smith, Shetland Documents, 1195-1579 (Lerwick, 1999), p. 53 no. 53.Aonghas MacCoinnich, Plantation and Civility in the North Atlantic World: The Case of the Northern Hebrides (Brill, 2015), p. 72. The assailant from Lewis, traditionally described as Hucheon MacLeod, seems to have been Hugh Clan Morrison, brieve of Lewis, of Trotterness, who killed Olave's son, Henry Sinclair, around the year 1551.John H. Ballantyne & Brian Smith, Shetland Documents, 1195-1579 (Lerwick, 1999), p. 71 no. 106: Aonghas MacCoinnich, Plantation and Civility in the North Atlantic World (Brill, 2015), p. 72. In October 1564, Mary, Queen of Scots granted Sinclair a remission from prosecution for this crime.James Beveridge & Gordon Donaldson, Register of the Privy Seal, 5:1 (Edinburgh, 1957), p. 500 no. 1764.
As foud, Sinclair collected feudal rents in money and farm produce due to the Scottish crown and sent them to Edinburgh.Gilbert Goudie, 'Fouds, Lawightmen, and Ranselmen of Shetland', PSAS, 26 (March 1892) p. 191 Rents typically included dairy produce, and the butter, known as the "fat goods" was barrelled in Kirkwall on Orkney and shipped to Leith.Michael Pearce, "Account of George Wishart of Drymme", Miscellany of the Scottish History Society, 17 (Edinburgh: SHS, 2025), pp. 4–5, 8–10, 17. The skipper Robert Boswell took empty barrels and salt to Kirkwall. The produce was sold by the queen's argentar Alexander Durham to contribute to the household expenses of Mary, Queen of Scots.John H. Ballantyne & Brian Smith, Shetland Documents, 1195-1579 (Lerwick, 1999), pp. 251-269: Gordon Donaldson, Third of Benefices (Edinburgh: SHS, 1949), p. xl: James Kirk, Books of Assumption (Oxford, 1995), p. 655 fn. 2: Exchequer Rolls of Scotland, vol. 19 (Edinburgh, 1898), pp. 197, 251, 349. The fat goods were accounted in a local measure called a lipsund.Peter Anderson & John Ballantyne, Personal Correspondence of Sir John Bellenden of Auchnoull (Edinburgh: Scottish History Society, 2023), p. 37.Jennifer Harland et al, "Produce from the Isles", Farmer's Trades and Markets (Sidestone, 2025), pp. 187–197 Sinclair's merchant network included William Mudie of Breckness, Chamberlain of Orkney, John Hart of the Canongate, and Andrew Lamb of Leith and Southtyre.John H. Ballantyne & Brian Smith, Shetland Documents, 1195-1579 (Lerwick, 1999), p. 111 no. 152: Gordon Donaldson, The Renaissance and Reformation in Scotland (Edinburgh, 1983), p. 158.
Olave Sinclair and David Scollay, a burgess of Kirkwall bought a proportion of the Orkney produce or "victual" of 1562 for £295 Scots.Michael Pearce, "Account of George Wishart of Drymme", Miscellany of the Scottish History Society, 17 (Edinburgh: SHS, 2025), p. 9. Orkney produce was recognised in Scottish court culture. In December 1566, during an entertainment written by George Buchanan for the baptism of James VI at Stirling Castle, Latin verses were sung by nymphs and satyrs in honour of the food and hosts, and characters represented the Orkney Islands.'Pompae Deorum Rusticorum dona ferentium Jacobo VI & Mariae matri eius, Scotorum Regibus in coena que Regis baptisma est consecuta', in George Buchanan, Omnia Opera, vol. 2 (Leiden, 1725), p. 405
Sinclair was the proprietor of several farms.Brian Smith, 'Shetland, Scandinavia, Scotland', Grant G. Simpson, Scotland and Scandinavia, 800-1800 (John Donald, 1990), p. 31. He obtained the south house of Reawick in Sandsting by exchange in 1544. In July 1558, Scottish ships from Aberdeen, the Meikle Swallow and Little Swallow, attacked an English fleet. The Scottish sailors took cattle and other goods belonging to Sinclair on Mousa. Sinclair claimed compensation from the owner Thomas Nicholson in the Edinburgh courts.John H. Ballantyne & Brian Smith, Shetland Documents, 1195-1579 (Lerwick, 1999), pp. 49, no. 71, 92 no. 129.
Sinclair's receipts were recorded in the Exchequer Rolls prepared for Murray of Tullibardine as Comptroller. In 1566 he returned £1126 Pound Scots and £330 worth of cereal. The fat goods and wadmell of 1566 were sold to an Edinburgh merchant Robert Watson. Sinclair was censured for not seding his accounts in time to the Privy Council in Edinburgh.John H. Ballantyne & Brian Smith, Shetland Documents, 1195–1579 (Lerwick, 1999), pp. 114–115 nos. 155, 156, 121 no. 163.
In 1567, Sinclair collected £1159.George Powell McNeill, Exchequer Rolls, vol. 19 (Edinburgh, 1898), pp. 333, 376. In subsequent years the Shetland rents were recorded as receipts from Robert Stewart, 1st Earl of Orkney.George Powell McNeill, Exchequer Rolls, vol. 20 (Edinburgh, 1899), p. 339. The Foud owned or maintained a ship, in 1568 the skipper was Robert Boswall.Peter Anderson & John Ballantyne, Personal Correspondence of Sir John Bellenden of Auchnoull (Edinburgh: Scottish History Society, 2023), p. 92.
Sinclair's official work included writing licences and testimonials in favour of Hanseatic League merchant skippers like Johan Kordes of Bremen who was given a permit to use the haven of Baltasound in 1560. In August 1563, Sinclair wrote to the burgomaster and town council of Bremen about Kordes and his unlicensed competitors, who were exhausting the island resources.John H. Ballantyne & Brian Smith, Shetland Documents, 1195-1579 (Lerwick, 1999), pp. 80 no. 121, 104-5 no. 140.Bart Holterman, The Fish Lands: German trade with Iceland, Shetland and the Faroe Islands (Walter de Gruyter, 2020). HANSdoc Database, Bremen 2-R.11.kk, Bart Holterman, 2017 In September 1567, Sinclair prepared a testimonial for Gerdt Hemeling of Bremen whose ship and cargo of salted fish had been taken from his trading base at "Drosteness" (Dunrossness) by the Earl of Bothwell, who was briefly Duke of Orkney. Sinclair employed a legal clerk or writer called Peter Hog who was the scribe of his official documents and helped Sinclair add his signature with his "hand led on the quill". Hog was called the "Sheriff Clerk of Shetland". Sinclair's servant Henry Nauchty also wrote documents.John H. Ballantyne & Brian Smith, Shetland Documents, 1195-1579 (Lerwick, 1999), pp. 123-5 nos. 166, 167.
A Scottish chronicle, the Diurnal of Occurrents mentions that Bothwell had dinner with Sinclair in Shetland in August 1567 after his flight from the battle of Carberry Hill. Diurnal of Occurrents (Edinburgh, 1833), p. 123 The English ambassador in Edinburgh, Nicholas Throckmorton, wrote that Sinclair, the "principal man of the Isle named Fogge", was a supporter of Bothwell, and would help Bothwell escape the pursuing force led by William Kirkcaldy of Grange and William Murray of Tullibardine.Robert Keith, The History Of the Affairs of Church and State In Scotland, vol. 1 (Edinburgh, 1734), pp. 458-9 citing British Library Cotton Caligula C/I f.48.
In January 1568, Bothwell wrote of his meeting with the Bremen merchant and skipper Gerdt Hemeling at Sinclair the receiver's house, probably meaning the house at Brow near Dunrossness.John H. Ballantyne & Brian Smith, Shetland Documents, 1195-1579 (Lerwick, 1999), p. 126 no. 171. He had hoped that Hemeling's ships and those of a Hamburg trader would join his fleet. Grange and Murray arrived at Unst and disturbed Bothwell's plans. He joined with the Hamburgh merchant at Scalloway and sailed to Norway.John Hosack, Mary Queen of Scots and her accusers, 2 (Edinburgh: Blackwood, 1874), p. 592: Agnes Strickland, Letters of Mary, Queen of Scots, vol. 1 (London, 1842), pp. 245-8. Bothwell took the Pelican, one of Hemeling's ships, with him.John H. Ballantyne & Brian Smith, Shetland Documents, 1195-1579 (Lerwick, 1999), pp. 121, 128: James Beveridge, "Lady Anne Bothwell: The Scottish Lady", The Scottish Historical Review, 1:4 (July 1904), p. 384: Gilbert Goudie, Diary of the Reverend John Mill (Edinburgh: SHS, 1889), p. lxxxviii fn.
Olave Sinclair wrote a testimonial for Gerd Hemeling on 15 September 1567 at Laxfirth. It stated that the Bremen merchant traded at the harbour of Drosteness (Dunrossness) and paid his customs. Bothwell had taken a ship from Dunrossness and spoiled its cargo of salt fish.John H. Ballantyne & Brian Smith, Shetland Documents, 1195-1579 (Lerwick, 1999), p. 123 no. 166.
Olave Sinclair made his will in 1571 and divided his estates between his three sons according to traditional udal law.T. Manson, 'Shetland in the Sixteenth-Century', Ian Cowan & Duncan Shaw, The Renaissance and Reformation in Scotland (Edinburgh, 1983), pp. 207, 209. James VI confirmed the ownership of lands by his son William Sinclair in March 1579.John H. Ballantyne & Brian Smith, Shetland Documents, 1195-1579 (Lerwick, 1999), p. 241 no. 260.
Arthur Sinclair of Eisweck (Eswick) was Sheriff Depute of Shetland in March 1572.John H. Ballantyne & Brian Smith, Shetland Documents, 1195-1579 (Lerwick, 1999), p. 144 no. 190. Laurence Bruce was appointed tacksman of the foudry in 1571, and was known as the foud.Peter D. Anderson, Robert Stewart, Earl of Orkney, Lord of Shetland (John Donald, 1982), pp. 167-8. By April 1573, Bruce was "undoubted foud, sheriff depute and chamberlain of Shetland".John H. Ballantyne & Brian Smith, Shetland Documents, 1195-1579 (Lerwick, 1999), p. 151 no. 199.
Complaints against Laurence Bruce in 1576 included the use of false measures to increase the profit of customs and duties. For almost 30 years, farmers on Bressay had used a weight for butter called a "bismeyr" made with Olave Sinclair's consent by William Urving of Trondra. Bruce introduced a new larger "bismeyr".John H. Ballantyne & Brian Smith, Shetland Documents, 1195–1579 (Lerwick, 1999), p. 195.
One of his sons was contracted to marry Katrine Halkat in 1547. She was a daughter of Robert Halkat, kirk minister of North Maving or Northmavine.John H. Ballantyne & Brian Smith, Shetland Documents, 1195-1579 (Lerwick, 1999), p. 58 no. 84. A daughter married Richard Leask, who was murdered in a feud by a servant of Henry Sinclair of Sandwick.Gilbert Goudie, Diary of the Reverend John Mill (Edinburgh: SHS, 1889), p. 177.
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