Canada's most notorious criminal gets in the ring: 1935: Gary Will's TWH

"Much of what Ryan said and did will be forgotten, and it cannot be too soon."
Toronto Daily Star editorial, January 11, 1924

What Norman "Red" Ryan said and did are, indeed, now being forgotten. But for many years after the Star's editorial, Ryan was perhaps the best-known criminal in Canada. And his notoriety -- ironically, aided greatly by the Star -- only grew through the 1920s and 1930s.
Ryan became well-known as a bank robber whose exploits were romanticised, in a Bonnie & Clyde kind of way, by the newspapers of the day (a young Ernest Hemingway even wrote a story about him). We won't review Ryan's criminal career here—Peter McSherry's 1999 book The Big Red Fox goes into such details and is probably available from most public libraries in Canada—but after serving 11 years of a life sentence, Ryan was paroled from Kingston Penitentiary in July 1935 with the support of the prison chaplain and even Prime Minister Richard B. Bennett, among many others.

He was considered to be the model of a reformed prisoner. Shortly after his release, he wrote a series of stories for the Toronto Daily Star and when news got out that letters his wife had written to him had been confiscated by prison staff and sat in the warden's cupboard for 14 years—while Ryan was allowed to believe that she had died—he even became a symbol for prison reform. A car dealership in Toronto hired him as a salesman and invited people to buy a vehicle from the famous Red Ryan.
Just a few weeks before he'd been paroled, Ryan was allowed out of prison to attend his sister's funeral in Toronto -- something that was almost never done in that era. According to McSherry, Toronto wrestling promoter Jack Corcoran met with Ryan after the funeral:

Afterwards, Jack "Corky" Corcoran, a prominent Toronto wrestling promoter, who [penitentiary chaplain] Father Kingsley had involved on Ryan's behalf, came by in his new 1935 Chrysler sedan and took Ryan, [Ryan's brother] Russ, and the guard on a drive about a much-changed city.

Two weeks after he was freed, Ryan was spotted attending Corcoran's wrestling show at Maple Leaf Gardens.

There's a new wrestling fan in Toronto and he says it won't be his fault if he ever misses a show. The newcomer to the ranks of the mat addicts is Norman "Red" Ryan and he admits that he was positively amazed when he saw the mastodons of sport turn on the heat at Maple Leaf Gardens last Thursday. ... The "rasslin" bug must have bitten Ryan for the next night he motored over to Hamilton to see Sammy Sobel's show and he was the first in to Jack Corcoran for tickets for the Meyers-Cantonwine brawl of tomorrow night. — Lou Marsh, sports editor, Toronto Daily Star, August 14, 1935

Not only did Corcoran bring Ryan to the shows, he hired him as night manager for his Nealon House hotel on King Street East. Ryan greeted guests and booked entertainment, along with running errands to Maple Leaf Gardens and other places. Writes McSherry:

Ryan's employment with Corcoran also involved him in the activities of the Queensbury Athletic Club, for he was, after all, a huge celebrity in Toronto and his currency could be exploited in more than one way. On one occasion, Red Ryan was introduced into the ring at a Maple Leaf Gardens wrestling card while a multi-coloured spotlight bathed him in light.

Corcoran also let the 40-year-old Ryan work out with Freddy Meyers two days before Meyers' main event match against Howard Cantonwine (Ryan is the one facing the camera in the photo at top).

Ryan weighs 210 pounds and Meyers tried to sell him the idea that he should turn to wrestling as a profession. "Red" didn't hesitate a second. He said, "Nay, nay" in the most emphatic tones he could muster.— Lou Marsh, sports editor, Toronto Daily Star, August 14, 1935

As events would unfold, both Marsh and Ryan would be dead within 10 months of the date that story was written. Marsh died unexpectedly in March 1936. Ryan was one of many who attended the funeral -- as was Corcoran, Marsh's good friend.

According to McSherry, Ryan -- who still worked at the Nealon House -- attended a Corcoran wrestling show in Oshawa on May 21 and was planning on moving out west. Three days later, and just 10 months after his release from the penitentiary, Ryan was shot to death by police as he and an accomplice tried to rob a liquor store in Sarnia.

Before he was killed, Ryan coolly shot and killed 33-year-old Constable John Lewis, the first policeman to arrive on the scene. Following Ryan's death, there were rumours that he had recently committed other robberies and two murders. It was one of the biggest news stories of the year and led to a severe tightening of the parole system in Canada's prisons.

Corcoran and John Tunney attended Ryan's funeral at Mount Hope Cemetery.

-by Gary Will