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My Sinclair Ancestry – The Mystery of James Sinclair the Ploughman

Where does my Sinclair surname come from? The simple answer, as with most Sinclairs from Scotland, is Caithness in the far north. But the detailed answer is far from clear. This is the first of several articles I shall be publishing about the search for that name, who it came from, and what is yet to be discovered.

This blog will describe the search for the earliest known Sinclair ancestor of mine, who can only be identified back to 1887: James Sinclair.  I do not know where he came from before that year, nor do I know what happened to him after that year. He is a complete mystery. The second piece, which will follow this one, will tell of the life of James’s son, my great grandfather, also named James but known as Jimmy Sinclair, born in Caithness in 1887.

 A lot more is known of Jimmy, who held me, as a baby, in his arms in Edinburgh where he lived for most of his adult life, married to May Jane Maguire. A future post will explore how I have used DNA, and particularly YDNA (that of the male chromosome handed down only from fathers to sons), to try and find the truth of my Sinclair past. That past is still a mystery. I hope by sharing these stories, of lives and of research, that someone, somewhere, may help unlock this mystery. If not, these articles will stand as a record for all that I know, and eventually be published in a book about my family history. To go to the blog about the life of Jimmy Sinclair, son of James Sinclair please click:

My Sinclair Ancestry – Jimmy Sinclair, 1887-1964

Of the Sinclair pieces coming out on this site, this first one will of necessity record the most detail of research that has been undertaken. As will be read below, it sadly becomes a list of one area after another which has been examined in depth but with no answer found. Such, sometimes, is the nature of genealogical research. The only solution is to keep going. I had desperately wanted to solve this mystery for my Dad’s sake whilst he was still alive, but did not manage to – he died in 2019. Yet breakthroughs can sometimes occur out of the blue, so I shall never give up.

James Sinclair Birth Record from 1887

The facts from 1887 are as follows. My great grandfather, Jimmy, was recorded as being born James Sinclair, on 2 September 1887, in a house in Wick High Street. His parents were named as James Sinclair and Margaret Simpson. They signed their names to that effect. The birth was assisted by Jimmy’s grandmother, Mary Simpson (maiden name Cook), who was a midwife. It took place in a dwelling where some of the Simpson family were living, having moved away from the Isle of Stroma off the northern coast, where they originated.

Jimmy Sinclair as a baby with his grandmother Mary Simpson (born Cook)

Jimmy’s mother, Margaret Simpson, has a clear family history which can be traced forward to this day and back in time through many generations living on Stroma. She and her Simpson family have numerous descendants who still live in Caithness, mostly in and around Thurso and along the north coast. Those who I know now, mostly come from the families of Simpson, Sutherland and Mackenzie, and it was a joy to meet up with a dozen or so of them when I visited in 2022. In spite of several generations difference in our cousinly connection, they all treat me as close family.

With Simpson descended cousins in Thurso, Caithness, July 2022

Margaret’s story will be told another time. Suffice to say that she was born on Stroma, which lies north of Caithness between the mainland and Orkney. In 1887, she was working, as a domestic servant, at Barrogill Mains, a farm attached to Castle Mey in the north of Caithness. She was to return to her job there a while after Jimmy’s birth, whilst he remained with her Simpson family in Wick, with whom he grew up.

Margaret Simpson in the 1880s - from the Johnston Collection
Margaret Simpson (now Dunnet) in the 1940s

Who Jimmy’s father was, and what happened to him after the birth, is the biggest mystery in all my family tree. On the birth record, he is recorded, with his own signature, as James Sinclair, father. His occupation is listed as Ploughman. Under his name is written Hillhead, which is probably where he (as opposed to Margaret) was from.

After the birth, almost nothing was ever heard, or recorded of this James Sinclair. Family rumour, through Jimmy’s half-sister, Minnie, who I used to holiday with as a child in Huntly, North East Scotland, was that James died tragically soon after the birth, drowned in the Pentland Firth which lies north of Caithness including around Stroma. Nothing is known of James before 1887, not his place of birth, his parents, where he lived, or any other family members. Other than the supposed death by drowning, no information has been passed down the generations as to who James Sinclair was.

Minnie Dunnet (became Rhind) who passed down the tale of James Sinclair drowning. Minnie lived with Jimmy Sinclair in Edinburgh in the 1920s when training then working as a nurse, so she knew him well and was his closest (half) sibling.

For several years, my father searched for details of James and what happened to him. Over the last decade, I have continued that search. Neither of us found anything, nor have other family who have looked. This has undoubtedly not been helped by the fact that James Sinclair was probably the most common male name at that time in Caithness, the county being where the Clan Sinclair come from, and James being such a popular name at that time in Scotland.

Below are listed the outcomes to date of the umpteen searches my parents, I and others have undertaken for James Sinclair the Ploughman. Occasionally there has almost been a breakthrough, when a vague connection was found, but none of these have proved substantive.

There were several ploughmen called James Sinclair listed in Caithness newspapers during the 1880s, often appearing in ploughing competitions, but their details cannot be specifically identified. It was by nature an occupation which was needed more at some times of the year than others, so ploughmen tended either to move around a lot, or to work in different ways in the winter months, such as fishing or other land work.  

The name Hillhead applies to a number of different locations in Caithness, as well as further afield ranging from Sanday in Orkney down to Glasgow. Locally, there are Hillheads in Sarclet, Latheron, Dunnet, and Wick. The latter would seem most likely as Jimmy was born in Wick, and there was a Hillhead Farm just to the north of Wick which employed ploughmen, but there is no record in censuses or valuation rolls of a James Sinclair living or working there in the 1880s. These days that area is called Hillhead, and there is a Primary School of that name there.

From censuses and birth records, there were scores of James Sinclairs in Caithness and further afield who were of an age to have fathered a child in 1887. None has been found with an address linked to a Hillhead (living or born there). Nor has any definitive suspect been found of that name in a census. Farming, crofting, blacksmith and ploughmen connections have come up, but nothing precise enough to follow up. One ploughman became a Railway Porter, moved to Edinburgh and had more children, but his signature is very different from that on the birth record, so no connection can be proved.

Several James Sinclairs are recorded as dying at sea in the years after Jimmy’s birth, but none of these events occurred near Caithness, nor is there often any way of knowing the background of any recorded as dead at sea as no details are given on any available death certificates. One James Sinclair from Forss, Caithness, a 38 year old carpenter, died at sea near Le Havre of Heart Disease, but there is no way of knowing if this was the right James. One death involved cannibalism, which was interesting if unpleasant, but as with all the others it was impossible to know where that James Sinclair had come from.

Many newspaper articles of that period record deaths at sea of local fishermen and sailors in and around Caithness and Orkney. Some were Sinclairs, but none name a James Sinclair.

No graves in Caithness have been identified which show a death of a youngish James Sinclair in the years immediately after Jimmy was born.

Margaret Simpson had a child with another man, John McGregor, five years after Jimmy was born, then married a different man, John Dunnet, two years after that, and had four or five children with him – one of whom was Minnie (Williamina Dunnet) from whom the family tale of James’s drowning came from. One of my fondest possessions is the Dunnet Holy Bible, listing family members back to 1824. 

Most Kirk Session records have been checked in Caithness for that time and no mention was found of James or the birth – although it was discovered that Margaret sought payment from John McGregor for her daughter by him, born after Jimmy.

Kirk Session record from 1892 showing that Margaret Simpson ensured that the second father of one of her children, John McGregor, paid Paternity costs to her - there is no record of anything like this regarding James Sinclair.

No emigration, army or prison records have been found with a relevant James Sinclair on them – checked on the possibility that he did not drown but went elsewhere, which I always hold as a possible explanation for his disappearance.

DNA has also provided no answers so far. YDNA tests indicate that there is no paternal line DNA that I share with the Clan Sinclair or its members, and the DNA is rather linked to a range of different surnames with Scottish, and more distantly Irish, links, none of which are Sinclairs. Autosomal DNA shows many Caithness connections but as the link is several generations back, it has not been possible so far to differentiate between Simpson and Sinclair ones, and there are few matches with any Sinclair names in their tree and none with the name in recent times. The best match has been with a Sinclair from Orkney, but he and I do not share YDNA which confuses the picture – he is a true member of the Sinclair Clan, I am not. More of this will be described in the third, YDNA, piece which will appear on this site about the Sinclair search.

None of the people who I have contacted about this have been able to come up with anything new in the search, be they cousins, DNA matches, or researchers. None of Jimmy’s known descendants who have tracked down so far know anything either – that is no one who descends from any of his six Sinclair grandchildren, all born in Edinburgh: Eddie, David (my grandfather), Tommy, May, Joan, or Hughie.  I have advertised in many places online looking for known details and no one has been forthcoming. Cousins in Caithness have asked all their older relatives: some knew of Jimmy and a few had even met him, but none had any information about his father James.

Summer 2022 in Thurso Royal British Legion Club discussing shared Simpson and mystery Sinclair family history.

As James signed his name on the birth record, it seems likely, although not certain, that he was recording his real name. The drowning story seems less likely but still quite possible as Jimmy’s half-sister clearly believed it.

In genealogical research, it is important to stick to the known facts and pursue them mercilessly, but also to question assumptions and look for alternatives. I have done both, and thus far found nothing. I am sure that the above list is not exhaustive, but the searches so far have been. One day, maybe, a researcher, or a DNA match, or a cousin, might come up with a breakthrough. I would give a lot for that to happen, and will keep searching myself. But, sadly I will not be holding my breath.

Next time: the story of Sapper Sinclair from Wick – the life and in particular the military service of Jimmy Sinclair, Sergeant Major in the Royal Engineers.

2 Comments

  1. Peg Wiley

    Hello Malcolm. I’ve read both your blogs so far. Fascinating history on the church. Also, on James the Ploughman. I look forward to more of your writings!

    Cousin Peg Wiley

  2. Melissa Keigher

    Fantastic post Malcolm. Very much looking forward to parts II and III!

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