Tales of Wild Duncan

Tales of 'Wild Duncan' McGregor

Duncan McGregor was the brother of our great-great-grandfather John McGregor and great-uncle of our grandfather.  He was known for his feats of strength.  Among folk in the district and to his descendants, direct and indirect, he is known as 'Wild Duncan'.

The following are anecdotes about Duncan. I am typing the words directly, quoting from the work of Mr. Perkins Bull. Mr. Bull collected newspaper clippings of obituaries, marriages, and reunions and interviewed old folk in the district in the 1920's to 1930's.

He also made-up questionnaires to be answered. In short, he was a first-rate local historian. His papers are now in the Ontario Archives. They have been microfilmed: there is a set of the films in the Archives and one in the Chinguacousy Branch of the Brampton Public Library. The files are organized by surname. Thus, beside McGregor, there are anecdotes on Wilkinson and Standing as well. Hope you enjoy the following.

Interview with Mr. James Robson

"I remember hearing many stories of Dunc McGregor. One night he heard a noise in his house, and he went down cellar, and there he found a burglar, with his pockets full of Dunc's butter from the prints. Dunc didn't say much to him but made him come upstairs and he put some logs on the stove and made a real hot fire and then had the burglar sit close to it. Of course, the butter melted and ran down the burglar.

"One day Dunc walked into the hotel at Campbell's Cross.  This was when he was a fairly old man. He had a big sack of apples with him. He brought them into the hotel and turned down the sack around the edges until all the apples were nicely displayed. All the boys started helping themselves and I was outside looking through the window at this.

Then I saw Dunc go round locking all the doors and he got out a whip and he started flogging the boys and my! he made those boys skip and jump and he said "I'll learn you boys to take apples that don't belong to you

"Another story I have heard but which I am not prepared to vouch for was that Dunc carried a barrel of beer in a wager up the stairs to the verandah and threw it over.

"He met a man one day on the Etobicoke Bridge and he said to him. "Look here if you can throw your boot as far up the river as I can I'll throw you in." to which the man replied that there was no use in him trying because he knew he couldn't do it before he started. However, Dunc insisted, and the man took off his boot and threw it and of course Dunc threw his farther and so he did pick the man up and throw him in.

"Of course, this Duncan McGregor was just full of deviltry and always doing something like that. A person could tell stories about him all night. I am not prepared to say that any of the above stories were true. They are just what I have heard.

"Dunc and John, the two McGregor brothers lived across the road from each other and both became extremely wealthy men. In fact, Dunc died wealthy. Dunc's son Malcolm was a very clever fellow and went into the lumbering business up north. Dunc owned 350 acres of land in Caledon when he died. However, his son Malcolm went through most of it."

Fighting Days in Peel Now a Fireside Memory Caledon

Duncan McGregor, a dour Scot from Caledon Township, earned a widespread reputation as a man to avoid, although it is said to his credit that he rarely started trouble.  He usually ended it, however. His opponents would find themselves crushed in an embrace that would have surprised a bear. McGregor could lift a three-hundred-pound barrel of salt from the ground into the high wagons of his day with as little effort as the average man could heft a 100-pound bag of flour. One instance of his reputation for strength recites that he met three husky inebriates at Mono Mills one afternoon. The inebriated parties started a dispute and were all for a pitched battle. McGregor casually mentioned his name, and the warlike three turned and ran before McGregor made any move to step down from his cart.

McGregor met Jack Leary, bucko of Chinguacousy Township, at a tavern near Edmonton now Snelgrove, one night. Leary had tilted the glass once or twice at another tavern, and entering the room, offered to fight any man within twenty miles for $20.00. "I'll take ye," said McGregor from a dark corner of the room. "And who are you?" Leary inquired, swaggering over to the corner. "M name's McGregor, Duncan McGregor." "Ah'll have nothing to do with ye," said Leary. McGregor gently intimated that it would be a good idea for Leary to put up the drinks for the house, which Jack did. He did not wait, however, to drink with McGregor. He left.

Notes from Mr. Jos. Williams

"Mr. Jos. Williams remembers when they used to team grain from Caledon, east and west, to Port Credit. There was the McGregors and the Campbells and you couldn't go down too early in the morning to see a good scrap. One incident was that this McGregor played a trick on his neighbour. This neighbour had a load of grain ready to go to market the next morning and McGregor thought it was a good joke to go up and unload it after he had gone to bed. So, McGregor went up and unloaded the grain and put the wagon up straddle the ridge of the barn and then carried the grain up and loaded it all up again and hung a lantern on the end of it.

In the morning about 4 or 5 o'clock when the man got up to hitch up and take his load to town, he found out it was gone from the back door so he struck down to Dunc McGregor's. "Well", Dunc says, "Are you ready? Let's get away quick, I got to see a fellow down at Port Credit." And the man told him that his load of grain was stolen. Well Dunc says "Let's go on, you come with me and maybe we will catch up to. the person that took it". When they got down the road quite a piece, Dunc looked bac'1c, and he says, "What's that light back there, is that on your barn?" "By Jove it is", the man said.  "I'll bet my barn is on fire." So, he hurried back and when he got back to the barn he seen it was the lantern hanging on the back of his load of grain up on the ridge of the barn.  This was a Halloween trick that Dunc played on his neighbour and when the man got to town, him and Dunc settled it in the good old-fashioned way.  It was a good fight, but they broke even, neither one of them was badly damaged.

"They never seemed to go to bed in Brampton. No matter what time of night, you went down the street, you could always see a good fight."

Interview with Mr. Fred Haines, Cheltenham McGregors and McDonalds

"These people were quite a hardy crowd. I never saw them fight myself, but I used to often hear my father tell stories about them.

"McGregor was a very strong man. I remember hearing that one time he was out in front of the grocery store and there was a bag of salt lying there. He said to the storekeeper, "I could pick up that bag of salt and carry it off to my sleigh". The old fellow picked it up and walked off with it. I don't remember this happening myself, my father told me about it."

Annual Report of Peel Women's Institute Historical Research and Current Events

"Among the earliest settlers in this locality were the MacDonalds in the Mountain, who came in the latter part of the 18th century. The Smith's who settled on what is now known as the Brick-yard at Inglewood the McGregor's above Inglewood in 1820. The McColls in 1828. The McClarens and Balmers about the same time."

Archie McCall - Inglewood

"Duncan McGregor Sr. had a fine trotting horse named Tarry. He was always entered in the trots at the Caledon and Erin Fall Fairs.  His son Duncan, was a fine driver and always drove a horse named Buckskin, owned by George Patterson, who now resides in Brampton."

Interview with T.M. Elliott, Cheltenham Re: Gang Fights

"The McGregors and the McDonalds used to have gang fights, but I don't mind much about them. A fellow by the name of McGregor could stand and jump and kick the ceiling in the hotel."

Interview with Miss A.

"Have you any record of Duncan McGregor of Caledon who was a rabid Grit of samsonian strength?" "I did not see this but heard about it at bine(?). In those days when the Tories ruled in Peel with overwhelming strength, when John Millard Campbell and John Coyne were almightly, Dunc used to come for his supplies.

Outside of Chisholm and Elliott's store on the sidewalk were to be found barrels of salt in rows piled two deep. One day a lanky Tory said something politically unpleasant to Dunc who walked up to a prostrate 300 lb. barrel of salt gripped it by its rim in his teeth, and threw it over his head into the back of his sleigh- and­ proceeded to tie his tormentors into a bow knot which he might have done had it not been for the pleadings of his own friends."


McGregor file on microfilm Perkins Bull Collection

Genealogical Section, Chinguacousy Branch Brampton Public Library

Elizabeth McDonald

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Researched: July 2004

Transcribed: December 2007

Editors Note:   Elizabeth welcomes your feedback and  your stories you can share