Sinclairs of Roslin in Orkney

The first Sinclair who sailed over the Pentland Firth to Orkney was Sir Henry of Roslin (died sometime before September 1337), who had been appointed as King Robert Bruce’s baillie in Caithness prior to August 1321. Sir Henry had been charged with recapturing a fugitive accused of treason who had fled to Orkney, but the Norwegian baillies there refused to give him up. On reporting this back to the Scottish court, King Robert sent a letter of complaint on 4 August 1321 to the King of Norway, demanding (amongst other issues), that Alexander Brown, a Scottish subject, must be surrendered to his baillie according to the treaty both countries had signed at Inverness in 1312. Sir Henry had a base in Caithness at ‘Tannachkegis’, which Dr Barbara Crawford suggests was most likely Tannach, near Wick, and given the close association between Caithness and Orkney, having been one joint earldom under Norwegian rule for centuries, there were probably several other occasions when Sir Henry had to sail across the Pentland Firth.

Sir Henry’s heir, Sir William, made a prestigious marriage when he married Isabella, eldest daughter of Malise, Earl of Caithness and Orkney, from Malise’s second marriage to Margery, daughter of Hugh, Earl of Ross, and Mariota, sister of King Robert Bruce. Isabella would have been born sometime between 1325 and 1329, so she was quite young when they married sometime after 28 May 1344. The powerful Earl of Ross arranged her marriage, and he was also the King’s Justiciar ‘north of the Forth’. During Malise’s trial, having been accused of treason for selling his earldom of Strathearn to an Englishman, the Earl of Ross had been his advocate and protector. Sir William Sinclair would have also regularly sailed across to Orkney on his wife’s behalf to look after her property there, collecting the rents and dealing with the tenants, just as he did with her properties in Caithness.

Once their son, Henry, became the Earl of Orkney in 1379, more Scots and evermore Sinclairs appeared in the north; the earliest on record is a Thomas Sinclair who, in 1364, is recorded as ‘the baillie of the King of Norway’. This Thomas may have been the son of Thomas, the King’s standard-bearer who died in battle at Dunbar in 1296, a younger brother of Sir Henry of Roslin (the baillie of Caithness). A John Sinclair is noted as one of the arbiters in a case between Haakon Jonsson, the Governor of Orkney and the Bishop of Orkney in May 1369. Both Sinclairs were active in Orkney prior to Henry being granted the earldom and would have been appointed to those positions through the influence of the Earl of Ross. Moreover, Thomas had been appointed by the Norwegian King himself, indicating the Sinclair family had a close relationship with Norway already. When Earl Henry I died around 1400, all we know is that ‘he retired to the parts of Orkney and possessed them to the latter part of his life and died Earl of Orkney, and for the defence of his country, was slain there cruelly by his enemies.’ After Henry’s death, his mother Isabella is mentioned as overseeing the Orkney earldom on behalf of her grandson, Earl Henry II, who, it is believed, never visited Orkney. On Isabella’s death around 1418, Henry II’s brother John, was appointed ‘Lord of Shetland’ by the Norwegian King, confirming the Sinclair family enjoyed the continuing trust of the Norwegian King.

The incursion of Sinclairs into Orkney and Shetland continued; another Thomas Sinclair, possibly a son or grandson of Thomas, the baillie of Orkney and certainly a close relative, was the ‘Warden of Orkney’ in 1424, dealing with complaints of the people against David Menzies of Weem, whom Earl Henry II (died 1 February 1420) had appointed as guardian to the earldom during his son William’s minority. In 1438, a Thomas Sinclair, ‘son of the late Davy Sinclair’ is involved in a land dispute over Toab or Tollhope in Orkney. Alexander Sinclair is recorded as a witness for Earl William in 1446 and in 1455, and Sir John Sinclair was a cannon in Orkney until 1481. In 1480, Sir Christy Sinclair was a witness in an Orkney land dispute and it can be seen from Lord Henry’s Rentals, compiled between 1497 and 1503, that Sir John Sinclair had land in north and south Sandwick, a Gilbert and Richeart Sinclair were both in South Ronaldsay, the Bu of Karstane in Stromness was occupied by a Magnus Sinclair, whilst an Alexander Sinclair, David Sinclair, his son William, and a James Sinclair all held land in the Stromness area at reduced rents, which suggests a connection to the earldom family.

In the Skat of Shetland drawn up sometime between 1507 and 1513, we find Henry Sinclair in the lands of Skatness and Burrowland and Sande Sinclair in Sumburgh, all in Dunrossness. This Henry and Sande are likely ‘my brethers sons’ which Sir David Sinclair of Sumburgh, an illegitimate son of Earl William Sinclair, mentions in his testament in 1506, but which brother he refers to, is unknown.

Although their names are recorded, these growing numbers of Sinclairs in the islands cannot be linked into the earldom Sinclair family tree with any precison. Some of the many families may have commenced with illegitimate offspring of the early earldom Sinclairs, but we will never know because there are inadequate records during that time. All we do have is several of their later descendants’ insistence on their descent from the Sinclair earls, and as J. Storer Clouston commented, ‘the families of Warsetter, Essinquoy, Flotta, and Campston were all descended from Sir William Sinclair of Warsetter, though only the first legitimately.’ Sir William also spawned the Sinclairs of Strom and Brugh in Shetland and there may be other lines in the islands descended from his brother, Lord Henry, who certainly had at least one recorded illegitimate son William – he became the Vicar of Latheron in Caithness.

The lack of records in the islands can firstly be blamed on Earl Patrick Stewart who, during his tenure of the earldom in the early 1600s, deliberately destroyed all the records in Kirkwall, including the ancient Law Book of Orkney. Secondly, in 1657, Sir Oliver Cromwell had any remaining records in the islands packed up and transported south to Edinburgh by ship, which sank at sea in a storm. However, some records remained untouched in the Danish archives or in private hands and thanks to the sterling work of people such as Joseph Storer Clouston in his Records of the Earldom of Orkney and Brian Smith and John R. Ballantyne in their Shetland Documents series, the Orkney and Shetland Sinclair trees on this and the following pages are an attempt to bring the Sinclair family trees in the islands up to date, verifying the accuracy from the few original documents left; and where there is uncertainty, the entries have been marked thus: (?)

Nina Cawthorne


Sir Henry Sinclair, Lord of Rosslyn [baillie of Caithness] ( -bef. Sep. 1337) m. c.1306 Alicia de Fenton, dau. of Sir William de Fenton of Baikie (Angus) and Cecilia Bisset of Beaufort (Inverness)
(?) John Sinclair ( -bef.1336)
Margaret Sinclair ( -1418) m.(1) Sir John Sinclair of Herdmanston m.(2) Thomas Stewart, Earl of Angus
Sir William Sinclair, Lord of Rosslyn ( -bef.1367) m. Isabella ( -abt.1418), dau. of Malise of Strathearn (Perthshire), Earl of Orkney and Caithness, and Marjory, dau. of William, Earl of Ross
David Sinclair ( -aft.1391)
Henry I Sinclair, 1st Earl of Orkney, Lord of Rosslyn ( -bef.1402)  m.(1) (?) Florentia, Princess of Denmark, m.(2) Jean, dau. of Sir Walter de Haliburton, of Dirleton (East Lothian)
William Sinclair ( -bef.1469) m. Agnes (?) Chisholm [ancestor of Sinclair of Dryden]
John Sinclair [life-grant of the Lordship of Shetland, 1418] m. (?) Ingeborg, natural dau. of Valdemar, King of Denmark, and Tova Little, dau. of the Commissioner of Rugen
Beatrice Sinclair m. 1411 Sir William Borthwick ‘of that ilk’
Elizabeth Sinclair m.(1) Sir John Drummond of Cargill and Stobhall (Perthshire)
m.(2) aft.1428 Patrick Dunbar, Master of March
Janet Sinclair m. (?) Sir James Sandilands of Calder (West Lothian)
Jean Sinclair m. Sir John Forrester of Corstorphine (Edinburgh, Midlothian) ( -1448)
unnamed dau. m. William (or Alexander) Cockburn of Skirling (Peebleshire)
unnamed dau. m. (?) unnamed Heron of Marieton (Kirkcudbrightshire)
(?) Catherine Sinclair m. Sir Alexander Ramsay of Dalhousie (Midlothian)
unnamed dau. m. (?) unnamed Tweedie of Drumelzier (Peebleshire)
Mary Sinclair m. Thomas Somerville of Carnwath (Lanarkshire)
Marjory Sinclair m. 1409 Sir David Menzies of Wemyss (Fife)
Margaret Sinclair m. bef.1422 James Cragy of Huip, Stronsay (Lawman in Orkney)
(?) unnamed dau. m. unnamed Hay, Lord of Erroll (Perth and Kinross)
Henry II Sinclair, 2nd Earl of Orkney, Lord of Rosslyn (c.1375-1 Feb 1420) m. Egidia, dau. of Sir William Douglas of Nithsdale and Egidia Stewart
Beatrix Sinclair ( -c.1462) m. c.1425 James ‘the Gross’, 7th Earl Douglas, 1st Earl of Avondale
William Sinclair, 3rd Earl of Orkney, 1st Earl of Caithness, Lord St. Clair, Lord Chancellor of Scotland (c.1407-bef. 21 May 1480)  m.(1) Elizabeth ( -11 Nov. 1451), dau. of Archibald, 4th Earl of Douglas
William Sinclair, Baron of Newburgh [ancestor of Lords Sinclair] ( -1487) m. c.1458 Christian Leslie, dau. of George, Earl of Rothes, and Christian Haliburton of Dirleton
Sir William Sinclair of Warsetter [ancestor of Sinclair of Warsetter] ( -1523/7) m. Elene Gordon, dau. of Sir George Gordon, 2nd Earl of Huntly, and Elizabeth Hay
David Sinclair of Brugh ( -aft.1536)
William Sinclair ( -aft.1536)
Sir James Sinclair of Brecks (South Ronaldsay) ( -1536) m. Barbara, dau. of Andrew Stewart, Lord Avondale, and Margaret Kennedy of Dunure
Margaret Sinclair m.(1) bef.1550 James Tulloch of Lambholm (Orkney)
m.(2) c.1563 Magnus Halcro of Brough (Rousay)
Katherine Halcro (c.1558- ) m. Rolland Hamilton
Janet Halcro (c.1560-aft.1630) m.(1) c.1579 René Elphinstone of Hammiger, Stromness (Orkney)
Barbara Elphinstone (c.1580-aft.1623) m. J. Pearson of Newcastle, England
Robert Elphinstone of Hammiger (c.1582-1628) m. 1614 Elizabeth Smyth
Henry Elphinstone (c.1585-1607)
m.(2) bef.1609 William Sinclair of Eday ( -1624)
Gilbert Sinclair ( -1600)
Elspeth Sinclair ( -bef.1624)
Alesone Sinclair ( -aft.1624) m. c.1610 William Sinclair of Warsetter
Edward Sinclair ( -bef.1636) [eldest son, infest in his father’s lands, 1623]
George Sinclair [heir to his grandfather, 1636]
William Sinclair ( -aft.1636)
James Sinclair (-aft.1536)
Henry Sinclair ( -aft.1536)
Sir Edward Sinclair of Strom (Shetland) (nat. son) ( -1560) [ancestor of Sinclair of Strom and Brugh, Shetland] m. Margaret Dischington
Agatha Sinclair m. William Groat of Duncansby (Caithness)
Margaret Sinclair
Magnus Sinclair of Warsetter ( -bef.1546) m. Janet Keith ‘of that ilk’
John Sinclair of Tolhope [Sinclair of Tolhope] ( -bef.1579)
Magnus Sinclair ( -aft.1487) [witness for his father William ‘the Waster’ in 1487]
Elizabeth Sinclair m. John Glendonwyn of Glendinning and Parton (Roxburghshire)
Henry Sinclair, Lord Sinclair (c.1460-1513) m. Margaret Hepburn, dau. of Adam Hepburn, Master of Hailes, and Helen Home, dau. of Sir Alexander Home of Home

Map of Orkney (click to enlarge). Courtesy of Baynefield CartoGraphics Ltd

An impression of Earl Henry I’s castle at Kirkwall with St Magnus Cathedral and the Palace of the Yards. From ‘Cathedral, Palace and Castle: The strongholds of Kirkwall’ by Peter Anderson, in Stones, Scalds and Saints, edited by Doreen J Waugh.

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