The official record states that on 20th June 1940 he signed an application to join the Canadian Active Service Force. As he held the rank of Major in the 1st North British Columbia Regiment, he signed his application “John MacGregor, Major.” The application was approved and he was appointed to the 2nd Battalion with effect from the 1st July 1940. He was appointed company commander of one of the four companies in the 2nd Battalion.

The UNOFFICIAL story told by highly respected senior officers, differing only in respect of a few days in June 1940  is that on the 2nd June, John rode the ferry across to Victoria and enlisted as a PRIVATE in the 2nd Canadian Scottish Regiment commanded by Lt Col Babty. Now, during the inter war years, General Pearkes VC, Col Cy Peck VC, a Col Nicholson and John had all kept in touch and from time to time met to fight the war all over again. A few days after John had enlisted General Pearkes VC came to inspect the troops. The General marched along the ranks followed by Col Babty as Battalion Commander, by Major Horne as Company Commander,  then by Lt Green and finally by the RSM. The elderly and no longer quite so slim MacGregor stood at attention in the middle of the second rank as the inspecting party approached. Almost without stopping, as he passed John a poker faced General snapped “That man, in your office after parade.” A puzzled Col Babty repeated the order to Jack Horne, Jack repeated it to Lt Green and Denny Green, the Machiavellian planner, passed the order on to the Sergeant Major.

After the parade, a glaring RSM inspected John minutely from top to toe and found a thousand things wrong with his hat, his uniform his shoes, his bearing and ended up calling him “A sloppy soldier” and a disgrace to the Company, the Regiment and to the whole Canadian Bloody Army. The RSM himself marched him in to the office barking “Private MacGregor as ordered Sah.”

The General stared out of the window. Col Babty and Maj Horne were stood stiffly at attention in their own office wondering what it was all about. John, as befits a private soldier stared fixedly at a point in the distance. Then the General turned to face ‘Private MacGregor.’ “Where’s the ribbon Jock?” The General didn’t wait for an answer. “Major John MacGregor V.C. M.C. and Bar, D.C.M. They wouldn’t let you in I suppose. Well your bloody well in now.” He turned to address Col Babty. “You remember this man, he served you well in the last war and he will serve you well in this one. You’ve been looking for a new company commander. You’re lucky it’s going to be John.”

Having been instantly promoted John now needed a new uniform. Brigadier Jack Adams of Brigade HQ, a man who became John’s friend and was a pall bearer at his funeral takes up the story. He ordered a staff car and took John to the tailor’s shop the regimental officers used and recounts the conversation with the tailor thus:-

“I want this man measured for an officers uniform right away.”
“Well sir, I am pretty busy these da—“
“Today. Measure him NOW.”
“Yes sir, right away sir.”
When the measuring was done the tailor asked,
“A second lieutenant, sir?”
“A Major. And while you are writing it down, give him the 1915 Star, War Medal and Victory Medal.”
The tailor straightened up a little. “Yes sir. I have those myself.”
“Have you indeed? Now you can add a Distinguished Conduct Medal to those campaign ribbons. You do have one don’t you?”
The tailor seemed to be getting a bit agitated.
“A DCM? No sir. Never had call for one. Haven’t needed one all the time I’ve been in business. How soon would the Major like his uniform?”
“As soon as possible and let me see, I think you have a couple of Military Crosses too, don’t you John?”
John had picked up on what was going on.
“MC and Bar. Yes sir. I do believe I do.”
“You’ll have those in stock.” The Brigadier said, they’re common enough, but when you order the DCM you’d better get a VC ribbon as well. It’s just one of those isn’t it John?”
The tailor faints and the customers exit smiling.

In 1942, when Col Babty was re-assigned, John was promoted to Lt Col and took over command of the Regiment. From the records he seemed to be a hands on commander giving personal instruction to his recruits before handing them on to their fighting battalions. Throughout this time he was in and out of hospital, never for more than a few days but at a frequency that was unusual for a soldier.

In August 1943 he was sent to Britain for a 4-month detachment. He was able to meet his eldest son who had joined the Royal Canadian Air Force as a Pilot Officer. He was a rear gunner in bombers and been awarded a Distinguished Flying Cross. They both managed to travel to Nairn where John showed him around his childhood home.

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