Tag Archives: highwayman

The Dear Loved Boy

The romantic is cursed with a delicate type of blindness, a reckless folly that begins by meaning no harm yet which in the end will taint its imprudent victim with a painful destiny.

“He gained the love of ladies gay
None e’er to him weas coy
Ah, woe is me, I mourn the day for dear Gilderoy”

The romantic sentiment is made from a fey alchemy: soft feelings, gentle indiscretions.  It is responsible for the quiet dismissal of reality; replacing it with an insidious fancy that invades the dull fabric of reason like a golden thread.

“With muckle (much) joy we spent our prime
Till we were baith sixteen
And oft we passed the langsome (long) time
amang the leaves sae green”

Admittedly such a deadly attitude is not as common now as it once was.  This is a cynical world.  But centuries before it was not so much the case. Imagination was different – like prisms, thoughts of love and romance was split like gems to achieve an entirely new purity, a new light.  Men saw a woman’s pale skin as a fleshly metaphor for virtue and truth – though the feminine tint was laced with arsenic.  And women saw romantic possibilities in the dark eyes, slim figure and the feel of restrained muscular strength of her gentleman as he held her on the dance floor.  This was a generation easily deceived by their feelings, more than willing to travel the labyrinth of ardor that stretched before them.

“O, that he still had been content
with me to lead his life,
But ah, his manful heart was bent
to stirring feats of strife,”

Patrick Roy McGregor, known as Gilderoy, Gilleroy, Gilder Roy or Gillie Ruadh (“the Red-haired Lad”) was an outlaw of democratic tastes:  he was a robber, a blackmailer, a cataran (cattle thief) and a murderer.  He and his band of criminals terrorized the lands throughout Aberdeen during the early 17th century.

But he was pretty.  His white skin and auburn hair were not reconciled to his violent tendencies.  And the ladies loved his beauty and were happily blinkered from his misguided daring.  He was ‘bonnie’, ‘handsome’ and ‘winsome’.  Their yearning and tributes appeared in stories, ballads, prose and verse.

“My Gilderoy, baith far and near
was feared in every toon,
And boldly bore awa’ the gear
of many a lowland loon (peasant, rogue)”

The ‘arch rebel’ was finally apprehended in 1636.  McGregor stood trial in Edinburgh with his associates John Forbes, Alistair Forbes, Callum Forbes, George Grant, John McColme, John McGregor McEane, Gillespie McFarlane, Alistair McInneir and Ewin McGregor alias Accawisch.

“At length, with numbers, he was ta’en,
my handsome Gilderoy”

The charges were many; a miscellany of achievements of a dubious personality:  “tressonable usurpatioun of our Souerane Lordis royal power”,  “pat violent handes in the persones of the said Alexander (Hay) and his wyfe, tuik thame captives and prissoneris, for thair ransome and libertie”, involvement in a number of “crewall slauchters” or murders.    His choice of victims was an egalitarian one, preying on common folk, lairds and ministers.  He was supposedly betrayed by his mistress Peg Cunningham, and was able to stab her to death before being arrested.    Even more flamboyant tales claim that he robbed Cardinal Richelieu and picked Oliver Cromwell’s pocket…but a ruffian’s accomplishments had their limits.

He was found guilty on July 29.  The pleasantly fitting Scottish word for verdict (“doom”) was that McGregor be “drawin backwardis upone ane cairt…to the mercat (market) cross of Edinburgh.” Along with John Forbes he would be hung until dead on a gibbet that was considerably higher than that of their associates.  They were also to have their “..heidis be strukin af from thair bodies, with their richt handis, and the said Gilroy his heid and richt hand to be affixit on the eist or netherbow poirt of Edinburgh, and the said John Forbes his heid and richt hand to be put upone the wast poirt thairof.  (heads be struck off from their bodies with their right hands, and the said Gilroy his head and right hand to be affixed on the east or netherbow port of Edinburgh, and the said John Forbes his head and right hand to be put upon the west port thereof)

“To Edinburgh they led him there,
and on a gallows hung;
They hung him high above the rest,
he was sae trim a boy”

Such was his fame that a garden of ballads blossomed directly after his execution, such as “The Scotch Lovers Lamentation:  or Gilderoy’s Last Farewell…To an excellent new Tune, much in request”    Such popularity speaks of an ill-conceived pride, a stumbling thrill, a naïve delight…the ingredients of a misdirected affection. There are times when a passion gallops like an unrestrained fever, and its victim is unprepared to deal with the machinations of its subtle sickness – the extravagance of undisciplined emotion.

Thus having yeilded up his breath,
I bore his corpse away;
With tears that trickled for his death,
I washed his comely clay;
And safely in a grave sae deep
I laid the dear loved boy,
And now forever I must weep for winsome Gilderoy.

Jacobite broadside - Gilder Roy in his genuine Highland Garb.jpg


Stand and Deliver

The 17th century always had the appearance of a ripe old bawd:  good-natured, boisterous, and with a penchant for a pretty rogue.  Overflowing the stays of the 16th century, and with no interest for the baroque frippery of the century that would follow, the 1600’s were born out of taverns and plague, plots and intrigues, typhoid and flowers.

It was a lively time; one that welcomed audacity that was tempered with grace – a type of messy elegance that was not out of place on a muddy road, balancing instruments of persuasion, bullets primed.

It was the time of the highwayman.

These ‘gentlemen of the road’ were common to all centuries, but they seemed to thrive with a guilty panache during this one.  And as the 17th century seemed to possess a special bravura, it saw the blooming of a special kind of flower, ragged yet fragrant:  the highwaywoman.

There was the shoemaker’s daughter, Mary Frith:  ‘The Roaring Girl’, branded four times for thievery, escaping the gallows by the fortuitous means of a 2,000 pound bribe.  In her supposed ‘Confession’ she stated:  “I held very good Correspondence now also with those Grandees of this function of Thievery”.

Joan Phillips, respectable, beautiful and “…eminent for picking of pockets and shoplifting at all country fairs and great markets…”  Hung in 1685, her body was gibbeted:   left to rot in a cage to serve as a deterrent to all would-be miscreants, as well as making sure that it could not be removed for proper burial by her friends.

The ‘Wicked Lady’, Lady Katherine Ferrers, was an aristocrat and an heiress – her portrait shows a face framed with curls and pearls and  a smile that was both dangerous and discreet .  Married at 14, she took to the road in her husband’s absence – whether out of boredom or in order to build up her stumbling fortunes it has never been said.  A whimsical combination of the two situations would be the best guess.  Legend has it that she was shot during a robbery and later died of her wounds.  She was 26 years old.


Now, there is a ballad from around this time – known as “Sovay” or “Sylvia” or “Sylvie” – that tells a very pretty story.

It is about a young woman, about to be married, who is determined to test the loyalty of her fiancé.  She comes upon an idea, one that is typically robust, born from the earthy and daring mindset of the 1600’s.

Her lover, who has been away, is traveling back into town – she knows when, which coach he will be taking, down which rutted path it will be traveling.  The clever lady has decided to dress as a highwayman and waylay this vehicle, shivering with harness and brass traces protesting, and demand all goods that are held inside.

Should her young man willingly give up all his possessions, including his engagement ring, she would shoot him dead.

It is easy to imagine her standing thus:  the sweeping velvet hat, feathers curling to her shoulders, a dark cape reaching to her chin, heavy boots obscuring the feminine sweep of calf and thigh.  Brazen lace cuffs cowered in the breeze that raced unimpeded across the flat coaching road, obscuring hands that fingered two flintlock pistols.  It is easy to hear the clear, brave voice state the iconic demand, both romantic and criminal:  “Stand and deliver!”

Her lover did not.  And they lived happily ever after.

“I did intend and it was to know
If that you were me true love or no
For if you’d have give me that ring she said
I’d have pulled the trigger I’d have pulled the trigger and shot you dead.”