The Orangeville Desperado had a notorious career

Over the years this column has offered short biographies of Wellington County people who achieved fame and distinction elsewhere. There were also a few who built more dubious careers.

One of them was a fellow with the unassuming name of Bob Cook, who spent his early life in the Orangeville area. Beginning in 1906 he commenced a life as a criminal, famed for his aggressive nature and his skill at breaking out of jails, both locally and as far away as Colorado and Idaho.

As a young man, Cook involved himself in a number of bar fights and brawls. That got the attention of the authorities, but it was not unusual behaviour during that time for young men in their 20s. Most matured into lawful and useful citizens.

Bob Cook took a different road. As he grew older his antics became more violent and aggressive. In the fall of 1906, Cook attended the fall fair at Grand Valley. He became inebriated and violent, accosting strangers and taking a swing at people he did not like. The local constable soon wrestled Cook into a pair of handcuffs and escorted him to the Grand Valley jail.

Grand Valley authorities should have asked for their money back on their steel lockup. Cook sprung himself loose in less than two hours, and walked away and out of town with one of the bars as a souvenir. About month later, the county constable with two local officers attempted to arrest Cook in Orangeville. Cook pulled out a knife, cut one of the officers deeply across the hand, and then made his escape.

During the winter of 1906-1907 Cook left Orangeville and worked for the winter in a lumber camp in northern Ontario. He returned to Orangeville in late April. He was still on the “wanted” list there. When one of the town constables tried to arrest Cook, he produced a pair of revolvers, pointed them at the constable, and backed away, making good his escape.

Two days later Cook married a young woman named Florence Reid, who seemed to have seen something romantic in his law-defying behaviour. Cook realized that it would be impossible to live in the Orangeville area. The newlyweds hopped a train and moved west, settling in Oxbow, Saskatchewan.

That move did little good. Police traced the couple and advised the Mounted Police that Cook had a history back in Ontario. The Mounties arrested Cook, but the Orangeville police balked at the cost of bringing Cook home to face a court. When he was released, he and Florence packed their bags and moved from Oxbow to Boise, Idaho.

Bob Cook’s history with police in Canada was not known in Boise, but he soon built up a record there. Boise police arrested him for stealing a gun. He managed to break out of the jail, but his freedom was brief. Police arrested him again, this time for jail breaking, and he received an additional term in jail.

Cook served part of the sentence, plotting ways he could break loose. He engineered an escape that astounded authorities in Idaho, breaking out of the jail with a dozen fellow inmates. That jailbreak made headlines all over the Untied States.

In the ensuing months Cook was reported in other towns in Idaho, and towns to the south in Colorado. In October of 1909 he resurfaced back in Ontario. Reports of his return jogged the memories of police, who made plans to restore him to custody. His wife Florence had long abandoned him, claiming he was an abusive husband, and had returned to Ontario.

On the morning of Oct. 30 Bob Cook boarded a train to Orangeville. About noon he showed up at the door of Mrs. Thomas Reid, his mother-law. He didn’t seem interested in seeing his wife. Rather, he demanded some of his clothing, which he believed she had been storing. Mrs. Reid claimed she had none of his belongings. Cook began to utter abusive language, and then became violent, smashing some of Mrs. Reid’s furniture before he left, muttering threats under his breath.

That afternoon Mrs. Reid called on Magistrate Patullo, and swore out a complaint that resulted in a warrant for Cook’s arrest.

News of Cook’s return circulated through the area that evening. Two constables, one of them James Halbert, who had been wounded by Cook in the 1906 arrest attempt, spotted Cook on Broadway in the middle of the business section. The street was busy with Saturday night shoppers. Realizing he had been seen, Cook slipped into the Hughes and Norris men’s wear store.

The constables cornered Cook inside the store. He was menacing them with a knife. One of the officers, Sam Speers, grabbed Cook from behind, while the other, Jim Halbert, attempted to put handcuffs on Cook. He was not successful. Cook slashed Halbert’s hand and arm a number of times, cutting him at least twice to the bone. Halbert’s arm and hand were useless.

Cook then twisted out of the grasp of Sam Speers, and escaped onto the street. The confrontation had attracted a large crowd, but no one stepped up to tangle with Cook. He walked nonchalantly down the street and then disappeared from sight.

Meanwhile, several bystanders stooped to assist Jim Halbert, who was on the floor and bleeding profusely. They were afraid that he would quickly bleed to death, but someone soon had a tourniquet on his arm. Stout arms carried the constable to the nearby office of Dr. Henry. He managed to stitch the veins and arteries back together and bandage the wounds, but he told the constable that he would unlikely be able to use his thumb and forefinger again.

Bob Cook disappeared into the darkness after that confrontation, but he remained in the area. A couple of days later he discovered where his estranged wife was living, and delivered several threatening messages to her. On Nov. 4 Florence Cook boarded a train for Toronto. She went directly to the Attorney General’s office, where she gained an interview with the deputy minister. She told him that she was very fearful for her safety.

Since the attack on the constables the previous Saturday she stated that Cook had twice threatened her, and that Cook’s assault on Constable Halbert was the second of the kind. She told the official that her estranged husband was “a desperate lunatic and should not be at large.”

Florence Cook’s visit did produce some results. The attorney general’s office sent an investigator from Toronto to Orangeville to pick up Cook’s trail, and two county constables came as well to offer assistance. Florence’s visit to Toronto received wide publicity in the Toronto papers and in many of the weeklies in Southern Ontario.

The press coverage given to his escapades was probably sufficient to prompt Cook to leave the area at once. None of the police sent to Orangeville was able to pick up Cook’s trail. His name drops out of the local historical record.

Cook probably departed the Wellington County area at once, to return to the Land of the Free, where it was easy to assume a new name and invent an identity. Bob Cook, the Orangeville Desperado, was about 30 at the time, and had the potential to become a law-abiding citizen should he have chosen that road. Whether or not he did is a question that seems to be unanswerable.


Stephen Thorning