Light-fingered, youthful thief Orval Shaw was more of an annoyance than anything else.
Brought up in less-than-ideal circumstances, he had turned to stealing food and clothing to keep himself going and his antics kept the local police going as well.
Shaw was not very keen on manual labour but he did work, off and on, for his neighbours in the area of Bothwell, a small town in the Chatham-Kent region. His shenanigans, which largely entailed pulling a shirt from a clothesline or helping himself to cigars in the general store, were mostly minor irritations.
Within a few years, though, Shaw would find himself on the run, a fugitive from justice with every law man in Ontario searching for him. For a few weeks in 1929, Shaw was the most hunted man in the province. It was during this time that he paid a short visit to Barrie.
In and out of jail from an early age, Shaw had seen the inside of the Ontario Reformatory at Guelph a number of times and always went away unimpressed.
In 1927, he was up for another stay when he made a last-minute decision to ditch the escorting officer as he was being transferred to jail. The lazy youth was apparently fleet of foot and vanished into the bush under a hail of bullets.
The bush was as comfortable to Shaw as any well-appointed home. He was a skilled outdoorsman and a capable hunter of small game. He was also very good at navigating his way around and could move very quickly and easily from place to place.
Seemingly, the place where Shaw was most at ease was a large wooded area known as Skunk’s Misery. The source of the unusual name of this hardwood and swamp locale southwest of London, Ont., is unknown, but it was a newspaperman’s dream as coverage of Shaw’s escapades widened.
A year passed before Shaw was captured. Dubbed the ‘Mystery Man,' 'Cave Man’ or ‘Phantom’ of Skunk’s Misery, the story got so much coverage that police raids were advertised ahead of time, to the delight of readers who were following each update as if it were the next instalment of a radio soap opera. The police, understandably, were less than pleased.
In September 1928, the police nearly got him. They encountered him driving a stolen car on a country lane and gave chase. The police car stalled halfway across the road, blocking Shaw’s exit, which forced him to take to the fields in the auto. The police opened fire and, out of nine shots to hit the fleeing car, one managed to pierce Shaw’s wrist which caused him to wreck. Off into the woods he went and it was another month before the police had another chance with their quarry.
The October takedown of Shaw was less than dramatic. He was found sleeping in an abandoned cabin in Skunk’s Misery and surrendered peacefully after awakening to a circle of armed officers. That, of course, is not the end of the story.
As Shaw sat in the Kent County Jail, he contemplated his fate as he faced at least 20 charges. He might end up back at his least favourite lodgings, the Ontario Reformatory, or he might get a free train ticket to Kingston. Neither option was particularly appealing.
He had made a friend in the county lock-up, which was a good thing for him but not for his new pal, Peter Brennan. Shaw and Brennan were fairly alike with one exception. Both were averse to hard work, but Brennan chose to be behind bars in the winter months, often breaking minor vagrancy laws to pass the cold weather indoors.
Somehow, Shaw convinced Peter Brennan that breaking out of jail would be a good idea and that’s just what they did. The pair had been sent unaccompanied to the jailhouse cellar to dispose of some garbage when they discovered that one of the windows there had no bars.
On Dec. 22, 1928, they disappeared.
For more than a month, police searched Skunk’s Misery repeatedly, and responded to sightings everywhere in the surrounding area. When a constable near Guelph had a run-in with the duo, the search expanded to that area, but the trail again went cold.
In an unlikely place 200 kilometres away, a summer cottage in Bolsover, Ont., suddenly had a strange car in the driveway. A neighbour contacted the owner of the cottage who learned that the car had been stolen near Guelph. This information generated more interest among law enforcement than the average car theft report.
On Feb. 15, 1929, at three in the morning, four police officers began to encircle the Bolsover cottage. They quickly realized that their targets were already outside. Shaw and Brennan were questioned and, for a little while, it looked like the saga was going have an anticlimactic end. Then, the men bolted.
This time, of the bullets that followed, three of them lodged in the body of Peter Brennan and he fell dead.
Orval Shaw kept running.
The Barrie newspapers began to follow the case in earnest as the story got closer to home. Yet, Bolsover is located well beyond the eastern shore of Lake Simcoe, a nice safe distance away from our town.
That year was shaping up to be one of the best for a man so completely different from Orval Shaw. Ross Underhill was a successful man – grandson of a shoemaker, and son of a man who took that trade to another level and became the manufacturer of shoes.
When the elder Underhill found his health declining, he passed the reins to the younger generation, closed his original plant in York Region and made the Barrie location the company’s headquarters. Fred Underhill, Ross’ father, passed away in 1921.
By 1925, Ross Underhill was vice-president of Underhills Limited, the large shoe factory on Dunlop Street, east of Mulcaster Street. This lakeside plant employed 85 men and created many styles of shoes, much of it from the high-grade leather produced by the Barrie Tanning Company.
In 1929, as Shaw was dodging the law all over Ontario, Ross Underhill was quietly amassing a small fortune through the immense success of his family business. As the last of the four Underhill brothers to remain unmarried, Ross would have been one of the most eligible bachelors in Barrie.
Ross Underhill had plans, though. He had his eye on Agnes Gilchrist, a bookkeeper from Allandale and soon the pair were engaged. At the same time, plans were being drawn up for a most magnificent home to be built for them on High Street. A European honeymoon cruise was booked for July.
Meanwhile, Ross Underhill continued his daily routine of driving to his factory office and storing his shiny new Packard sedan, behind expensive tamper proof locks, in the garage there. Two security men kept watch. Apparently, no one told Shaw that the garage was impenetrable, so off he went with the Underhill auto on Good Friday, 1929.
Shaw took Underhill’s luxury car on a test drive through the back roads of southern Ontario. He stopped to show if off to some friends who were working at the Homewood Sanitarium near Guelph. The police then realized that their man was back in his home territory and picked up the hunt again locally.
On Easter Sunday, the performance limits of Underhill’s Packard sedan were put to the test as Shaw embarked on yet another car chase with the cops. Once he was far enough ahead of his pursuers, Shaw ditched the showy car unceremoniously on the side of rural road and took off on foot.
Ross Underhill was updated by the police and went immediately to Guelph to retrieve his battered vehicle. Inside the car was a collection of military surplus clothing, some dishes, a half-eaten loaf of bread, tools, and a stolen driver’s permit belonging to R.J. Turner of Shanty Bay.
The next month was filled with drama, but no Shaw sightings. The press jokingly called the police scouring of bush lots and chicken coops in southwestern Ontario the ‘Barnyard Derby’.
Local folks began to become sympathetic to the fugitive’s plight.
Ladies left extra pies out to cool on windowsills and farmers turned a blind eye to minor pilfering.
But every good run must come to an end. Two cars with five police officers were creeping through the poor roads of Skunk’s Misery one night when they spotted headlights coming toward them. Turning their own lights off in time, they managed to ambush the other car as it approached.
As he had always done, Shaw fled into the night, but police chauffeur Tom Riding shone the high-powered beam of his flashlight onto the subject until he caught up with him.
Riding tackled Shaw and the pair landed in a pile of old scrap bricks. In the tussle, Shaw scratched, kicked, punched and bit Riding and eventually clobbered him with a brick.
When the other officers arrived, the billy club of C.C. Northcott ended the melee and the legendary bandit was in custody.
With 31 charges stacked up against him, it didn’t look good for Orval Shaw. However, most of these were crimes that required local folks to give testimony and most were unwilling to do so.
In the end, only a handful of charges went to trial and Shaw did some time in Kingston for those. After that, he settled down, married, had a family and remained in the area, peacefully, for the remainder of his life.
Each week, the Barrie Historical Archive provides BarrieToday readers with a glimpse of the city’s past. This unique column features photos and stories from years gone by and is sure to appeal to the historian in each of us.
