On June 7, 1958, thousands of people gathered at the new Woodbine racetrack in Etobicoke[1] for the oldest and, arguably, the most prestigious horse race in North America, the Queen’s Plate. The pomp and circumstance drew a fashionable crowd, the upper crust of Toronto society—men sporting pin striped suits and top hats, and women in fur stoles preening for the cameras, despite it being sunny and warm that day. Fans were in high spirits, hotly debating who would win the coveted prize.
Toronto Star sportswriter Jim Proudfoot stated that, no matter the outcome, it would always be known as Stole The Ring’s Plate—for this favoured filly had provided much colour and controversy prior to the race. Unlike the other two main contenders, Caledon Beau and Foxy Phil—belonging to Toronto Maple Leafs owner Conn Smythe and mining executive James Boylen, respectively—Stole The Ring wasowned and trained by two relatively unknown sisters from a small farming community called Langruth in Manitoba. They are my ancestors, Blanche and Olive Armstrong. Their mother was Lizzie Mayor, my great-grandfather Harry’s cousin on my mom’s side of the family.
Blanche and Olive would not have become involved in horse racing without Willie F. Morrissey—a well-known Toronto character, one of the most “caustic, controversial and volatile men ever involved in thoroughbred horse racing”[2], who stunned the race circuit with his King’s Plate win in 1938 with a colt named Bunty Lawless. The story of how the Armstrong sisters became his associates will unfold below; for now, we head back to the 1958 Queen’s Plate, where Blanche was registered as Stole The Ring’s owner and Olive had stepped in to take over the horse’s training after her usual trainer, Edwin Hall, became incapacitated in hospital with asthma[3].
There was some question as to whether Stole The Ring would be fit for the race. She had banged her head against a starting gate during a workout and then she came down with croup, which kept her out of serious training for over a week. The Globe and Mail reported that she had been given the okay to race: “Miss Olive Armstrong admitted Sunday the 3-year-old star still has a slight cough. ‘Stole The Ring, coughed twice on the racing strip and again when being walked back to the barn,’ she said. ‘Dr. George Badame (veterinarian) and myself share the opinion that the throat danger is over. The filly will be ready for her speed test of a mile Tuesday’”.[4] Four days before the race, Olive reported, “’She’ll go Saturday for sure, and she’ll win. […] All she needs now is a short, brisk work Friday and she’ll be ready. ‘”[5]
Even before that, questions had swirled around Stole The Ring’s eligibility to race for legal rather than health reasons. Her name was the subject of a court case brought by the Ontario Racing Commission, which alleged it was insulting to a rival horse owner (apparently Willie Morrissey had a penchant for giving his horses names that were unflattering to his rivals and the Ontario Racing Commission declared a ban on several of the horses he bred and named; all of these horses had been owned by Blanche[6] and trained by Olive). In March, Blanche had announced that Stole The Ring would not be a starter in the Queen’s Plate; however, after seeking legal advice, they were given assurances that Stole The Ring could not be disqualified if she competed under her name. So, she was back in the running.
Further still, there was a bit of a kerfuffle as to who would pilot Stole The Ring on race day. The coveted jockey Johnny Longden was promised to another horse, but when his horse did not qualify for the Plate, he was suddenly free and—although Conn Smythe wanted him for Caledon Beau—Willie Morrissey swooped in and secured him for Stole The Ring. Al Coy was displaced as jockey for Stole The Ring and left without a horse to race until Conn Smythe stepped in and engaged him for Caledon Beau.
Joe Perlove, a Toronto Star sportswriter, ascribed all these uncertainties around Stole The Ring as “a tinge of cloak and dagger stuff casting a few wisps of fog about her”[7]. Still, she was favoured to win the Queen’s Plate. She had won all five races she entered in 1957, winning $33,980, and at race time she was the 6 to 5 favourite. She was considered one of the best 2-year-olds to race in Canada—”even the oldest habitués of the racetrack can’t remember a 2-year of any breed going that fast”.[8]
On race day, at about 5 pm, the jockeys and their horses paraded from the paddock to the racetrack for the feature race. Those with last-minute wagers rushed the betting wickets. The horses set up at the start line of the 1 ¼ mile track. The atmosphere in the grandstand shifted, becoming more subdued as fans sent prayers and performed lucky rituals for their wager. Sitting on the edge of their seats, they craned their necks, waiting for the moment the starting gates would fly open.
Thwack! Right out of the gates, Stole The Ring surged to the front. Midway, she was a couple of lengths in front of the pack, but Caledon Beau was gaining. Three quarters of the way she was still in the lead, and it looked like Johnny Longden, the jockey with the most wins in racing history, was going to win yet again. But wait, as the front of the pack reached the final turn, Stole The Ring drifted out, giving an opening for third-place Caledon Beau to make his move. Urged by his jockey’s whip, Caledon Beau charged the rail and took a small lead. Stole The Ring rallied, challenging Caledon Beau, but faltered and lost momentum. Caledon Beau easily crossed the finish line almost ten lengths ahead. Meanwhile, White Apache charged by Stole The Ring to capture second place, leaving the Armstrong sisters’ filly in third. The race took under 2 minutes.
Afterwards, Johnny Longden explained the loss, “She suddenly weakened. […] It was just too much to ask a filly to beat those colts at a mile and a quarter when she didn’t have a previous race. The fact she finished third proves she’s a fine filly.”[9] As he walked towards the jock’s room, he yelled out to Edwin Hall, “they won’t beat her again!”[10] The winning jockey, Al Coy said, “I could have gone out of the park and won that race. It was no contest after Stole The Ring ran out of steam”.[11]
The 1958 Queen’s Plate loss was a crushing blow for the Armstrong sisters. Never had they come so close to winning the Queen’s Plate (it would not be until 2006 that a woman trainer, like Olive, won the Queen’s Plate). Between the two Armstrong sisters, they would saddle a total of five horses for the Queen’s Plate between 1953 and 1959: Winter Lady (1953), Welcome Home (1954), O’Morrissey (1956), Stole the Ring (1958), and George Hardy (1959); however, that esteemed prize remained elusive. Looking back over their careers as racehorse owners, the absence of that gold trophy feels like a weight, a missing capstone in a remarkable life story. A story that has been lost to time, for as they say, no one remembers who came in second, or third in the case of Stole The Ring.
Olive and Blanche’s mother was a Mayor—Elizabeth Eleanor Mayor (Lizzie), indicated by #2 on the family diagram). Lizzie was the daughter of John Hollings Mayor (#1), the second youngest son of Thomas and Harriet Mayor, the original Mayor immigrants to Canada who settled the family in Innisfil (Barrie), Ontario. John Hollings married Elizabeth Ann Rawson in 1877. He and his eldest sister, Annie and her husband’s family, moved to the Port Huron area in Michigan. That’s where Lizzie Mayor (#2 – Olive’s mother) was born in 1891. When she was about six years old, the family returned to Canada, settling nearby other Mayors in Woodside, near Gladstone, Manitoba. Lizzie married William John Armstrong in 1907 and they had nine children, including Olive Rawson (#3) in 1916 and Christina Blanche (#4) in 1922 (Olive’s middle name, Rawson, is her grandmother’s maiden name).
The family farm was south of Langruth, a village on the west side of Lake Manitoba. Olive was the middle child of nine and Blanche was six years younger. Ironically, Olive had been frightened of horses when she first encountered them on the farm. With a quarter section (160 acres) of mixed farm, the family likely produced just enough to feed their large family, with a marginal surplus to sell. Olive was thirteen years old and Blanche seven when the Depression began—tough years for the family.
For young women coming of age in farming communities across the country, there was a certain lack of self-determination that some would have rebelled against. Even if a girl was lucky enough to finish high school, there were not many options other than to become a farmer’s wife, and this was not for everyone. When Olive was 20 years old, presumably unattached and needing to find work, she left home and moved to Toronto. She found work as a waitress at The Hotel Morrissey on Yonge Street north of Bloor. I wonder if she had an offer of employment before leaving home. A couple of clues lead to this conjecture. First, her employer at The Hotel Morrissey, Willie F. Morrisey, was Irish like Olive’s father William Armstrong, and perhaps there was a family connection. Olive left home in 1936, the same year Morrissey bought the hotel, and it is easy to imagine him helping a friend who happened to have a young daughter looking for work. Upon arriving in Toronto, Olive briefly boarded in a house on Collier Street, just around the corner from the hotel—how did she find herself there unless she had specific reason to be in that area? True, she could have come to Toronto looking for work (a very gutsy move for a young woman in 1936) and after canvassing the employment opportunities nearby she sauntered into the hotel one day and Willie Morrisey, being the shrewd businessman he was, saw something beyond her pretty looks. But consider one final fact. Olive’s younger sister Blanche, and two of her brothers, Oliver and Sam, ended up working at The Morrissey too. Seemed like a family affair. [Note: her father William Armstrong was born and grew up in Quebec, moved to Dauphin, then Langruth and Morrissey was a Toronto Cabbagetown boy, so there’s no obvious evidence where their paths may have crossed.]
After she arrived in Toronto in 1936[12], Olive worked at the Hotel Morrissey for 17 years, first as a waitress, then housekeeper before becoming Morrissey’s private secretary in 1946. In a 1953 interview, Olive stated that her job was mainly keeping the books and generally helping at her employer’s horse breeding farm[13]. She’d been working for Morrissey for ten years when her siblings joined her in 1947. Blanche and her brothers, Oliver and Sam, each worked there for a ten-year span (1947 to 1957). Blanche started as a bookkeeper and became a “manageress” after two years. Oliver and Sam were hired as barmen and then worked as stewards, which probably meant they helped look after the property doing operational tasks[14]. Blanche and Sam also lived at The Morrissey (perhaps Blanche shared Olive’s apartment and Sam kept a hotel room); Oliver lived with their mother in an apartment in the neighbourhood known as Little Portugal. [Note: Their father William had died in 1942 and one other brother, Glennis, also moved to Toronto around this time, but he did not join the Morrissey enterprise; he was a car salesman]. Since the Armstrong siblings had such a close association with the Hotel Morrissey in Toronto, I wrote a short history of the hotel here.
Willie Morrissey founded the Ontario branch of the Horsemen’s Benevolent Protective Association (HBPA) in 1947, the same year Blanche and her brothers arrived (the HBPA represented thoroughbred racehorse owners and trainers on various issues in Canada and the US). In their administrative capacities, Olive and Blanche likely assisted with the association’s monthly meetings, which were held at The Morrissey. They would have met members of the Ontario Jockey Club and those involved in thoroughbred horse racing (Olive would name one of her horses George Hardy, after an honorary life member and advisor to the HBPA while Willie was president). At its second-ever meeting, the Ontario HPBA attracted 140 men to The Hotel Morrissey.
It was Morrissey who introduced Olive and Blanche to horseracing. Willie was a Cabbagetown newspaper boy who worked the carnival circuit and became a fight promoter before turning hotel proprietor. He bought his first horse in 1933. The first time he saddled a colt for the King’s Plate in 1938, he won. The horse—Bunty Lawless—became one of Canada’s greatest home-bred thoroughbred racing horses and was famous for siring winning offspring. Windfields, the key stallion in the founding of the racing and breeding empire of E. P. Taylor, is considered Bunty’s most important offspring. [Taylor dominated the Queen’s Plate, winning it a total of 11 times for his Windfields Farm, making him second only to J.E. Seagram, who won the trophy 20 times between 1891 and 1935.]
Around the time Morrissey started up the HBPA, he incorporated his horse-related interests under William F. Morrissey Ltd., with Olive as vice-president and Blanche secretary-treasurer. In 1949, the sisters turned to horse racing full-time. The financial arrangement that existed between them and Morrissey is murky. Olive and Blanche were employees of the company, and it was reported that all horse racing expenses were paid by the company and, therefore, all monies accruing (like winnings and horse sales) were paid to the company[15]. Yet, in a 1959 interview, Olive stated that she financed her first horse, Winter Lady, with winnings and her earnings as Morrissey’s employee, suggesting that she invested some of her own money[16]. To make it more confusing, the sisters “leased” horses from William F. Morrissey Ltd. (at least initially), registering as owners and racing the horses under their own names. If I had to guess about the leasing agreement, they probably paid a nominal fee of, say $1, something for the accounting books. To be an owner of a horse for a race, all you did was pay a fee, provide the name of the trainer, and register the horse under your name. It was common for breeders to register horses in their wives’ names. For example, when Willie Morrissey’s horse Willie the Kid won the King’s Plate in 1940, it was registered under his friend’s name, Mildred A. Kane[17]. The victory marked the first time a female owner won the Plate. How much she had to do with the horse is unclear—she was not the breeder, nor the trainer, and Olive or another groom were mucking out its stall.
Why do I care about the arrangement they had? I wonder about the motivation behind Willie adopting and funding Olive and Blanche’s horse racing pursuits. Was it a simple business decision—he could race more horses? Was it an effort to recede into the background and promote their names to get around some of his unpopularity with the Ontario Racing Commission and some track owners? Was it purely benevolence, helping the sisters out when they expressed interest in the horses? Perhaps it was some combination of all three. One clue that provides some clarity to his motives comes from a statement Willie made after he won the 1938 King’s Plate. He said, “I’m satisfied for the rest of my life; I never expected to live to see a day like yesterday. It was the best day of my life and I never expect to experience another thrill like the one it gave me to see Bunty win.” He declared that his ambitions had been met and no horse would ever race again in his silks for the Plate[18]. He held to that promise by running Willie the Kid under Mildred’s name, and perhaps his intention continued with Olive and Blanche (Willie later went back on this, running Arbor Vita in his orange silks in 1943 and he would saddle other horses later).
Whatever their arrangement, the first recorded race with Olive as a registered owner was in 1949, when she leased Hi Bunty from Willie. In the program, below, she is listed as the owner. She saddled Hi Bunty in the Ontario Jockey Club’s Spring Meeting, held at the original Woodbine Racetrack at the foot of Greenwood in the Beach neighbourhood of Toronto. (When the current Woodbine racetrack opened in Rexdale, Etobicoke in 1956, the older lakeside track was renamed Greenwood; for clarity I’ll refer to it as Greenwood even for events that took place there prior to 1956 when it was still Woodbine).
The sisters were then gifted horses by Morrissey. Olive was given a mare named No Mal Intent[19]—possibly named to remind her that she need not fear horses like she did when she was young. She ran the filly, winning the 1951 Cosgrave Trophy[20]. Then she bred the mare with Bunty Lawless, producing two foals named Winter Lady (1950) and Welcome Home (1951). Olive did well with both mares; they both ran the Queen’s Plate—Winter Lady in 1953 and Welcome Home in 1954.Blanche was given The Brat, who was mated with Siete Colores to produce a filly that was not destined for the racetrack but became a broodmare[21].
This list of horses owned by Olive and Blanche was compiled by reviewing newspaper clippings and is by no means definitive. The year indicates approximately when they raced as a 2- or 3-year-old.
In the beginning they would have worked as a team, with Morrissey overseeing the whole operation and making breeding decisions with their veterinarian and trainer, R.K. Hodgson. Olive and Blanche learned the ropes—how to care for the horses, executing training regimes, and deciding which horses to race. Edwin Hall, who started working for Willie Morrissey when he was 17, worked the horses, galloping them during training. Olive described rising at 4 a.m., seven days a week, to clean out stables, rub down and walk the horses or nurse them when they were sick, staying up all night at racing stables to ensure the horses remained safe, and assisting with the births. Olive explained the dedication, “You have to love horses, treat them with understanding and care, as you would a human being. If you treat a horse badly it behaves as a human being similarly treated behaves—real mean”[22]. Dave Stevenson, a jockey who piloted Olive’s 1954 Plate contender Welcome Home said in an interview, “I was just 17 in ’54 and (owner) Olive Armstrong wouldn’t allow me to use my stick (whip) on her horse”[23]. Later, Olive would own her horses outright and had learned enough to know when, in her words, “her animals are in the best fettle to run” a race.
To qualify for the Queen’s Plate, a horse must be 3 years old and foaled in Canada. Usually, a horse is nominated for the plate the year prior. Several stages of fees are paid, forcing owners to decide whether to run or scratch their nominated horse. The Plate trials are held the week before the event. They start with a long list of horses and run races until they have the fastest 20 or so horses (the total number can differ)[24]. The assignment of post positions for the Plate race are drawn randomly.
Just where did they keep their horses? Morrissey and the sisters used barns at Greenwood Racetrack to stable and train their horses or kept them at one of several breeding farms on the outskirts of the city. First, there was their veterinarian R.K. Hodgson’s farm in Markham (he bred and sold horses) and it was here that many horses overwintered if they were not travelling to the southern states for races. Then there was the popular Maryvale Farm in Scarborough, a breeding farm originally owned by horse enthusiast and founder of Laura Secord chocolates, Senator Frank O’Connor (later owned by the Lasalle Christian Brothers after O’Connor willed the 850-acre farm to them[25]). The Brothers continued to run the breeding farm, hiring a fellow named John Loughry to manage it and look after other people’s horses. They also sent their horses to the racetrack in Fort Erie for training.
In 1949, the same year the sisters turned to working with horses full-time, Willie bought his own farm in Etobicoke. The Morrissey farm was just north of Rathburn Road on the west side of Highway 27[26], not far from where the Woodbine Racetrack would be built seven years later. The farm had a 30-stall barn, a driving shed, and a small track for training horses when they were not at the racetracks[27]. In 1955 the farm held 34 horses (28 belonged to Morrissey), a combination of racing stock, sires, broodmares, and foals. The farm also had a modern house; in 1957, Olive along with her brother Sam and his wife Ruth were living there[28].
Olive was the first female horse trainer to be licensed in Ontario by the Ontario Racing Commission in 1953[29]. The requirements then may have differed, but to get a training license these days, you must pass three different tests, written and practical. She received a fair amount of press coverage as the only female owner-trainer on the race circuit. [Right, Source: Calgary Herald, 29 April 1953, p 38.]
Winter Lady was one of her best horses. The filly was born on January 13, 1950. In 1952, Olive raced her as a two-year-old with growing success. In May, she placed second in the Filante Plate[30] for 2- year-old fillies at Greenwood. That same month she placed 1st in the two-year-old race at the Ontario Jockey Club spring season meet.[31] In June she placed third in the My Dear Stakes at Thorncliffe.[32] In September, she won first place again in her division at the Ontario Jockey Club autumn season opening[33] at the same track.
In the lead up to the 1953 Queen’s Plate, she scored third in her division in the plate trial the week before the event[34]; the favourite, Canadiana, placed fourth. Sports reporters were curious about her and interviewed Olive. “Winter Lady did well right from the first. She outran the other yearlings at the farm, and we raced her lightly last year. She developed a slight nervous condition in the fall, and we eased up on her but when winter training started in January, she did everything asked of her.”[35]
On June 2, the same day as Queen Elizabeth’s coronation, competitor Canadiana, still the favourite, won the Queen’s Plate. Despite having trained since January and declared ready for the mile and quarter race, Winter Lady had a bad day, finishing 16th out of 19[36]. Following the Queen’s Plate, she had several top place wins. In July she won the Fort Erie Feature in an upset over Blue Scooter, and Olive was presented with a blanket for Winter Lady[37]. In August she placed 2nd in the Goodwill Stakes[38] at the Longbranch track, in September, she was 4th in the Fairbank Stakes[39], and then she won 1st in the Maple Leaf Stakes, which came with a purse worth $3,600[40]. Olive received the Harry C Hatch Memorial Trophy for this win. A couple of days later, she placed 2nd in the Breeders Stakes at Woodbine Park[41].
Olive and Winter Lady had further wins in 1954; in October, she won the Elmbrook Purse at Longbranch[42]—her odds were 26 to 1, so this made for a nice payout for those wagering on her. In October, she came first in the Brockville Purse feature race, but only because she ran free, that is, without a jockey; she threw him after she hit the side of the starting gate[43]. In November, she captured first in the Dufferin Feature[44]. Winter Lady continued to do everything asked of her, pulling in a decent purse from her wins and even becoming a broodmare after retiring from racing; everything but Olive’s dream of winning the Queen’s Plate.
Olive and Blanche travelled a fair bit in pursuit of horse racing. Moving horses back and forth between stables and the four racetracks within the city—Greenwood, Dufferin, Longbranch and Leaside—would have been a constant grind. Add to that the tracks further afield in Brockville and Fort Erie. They also travelled to Jamaica in Long Island, New York and Lincoln Downs in Rhode Island for the early spring racing season. They travelled to Florida in 1947, 1949, 1955, 1957 and 1958; possibly, they went each year for the autumn and winter campaigns there. They likely headed to the Florida Derby, an American thoroughbred horse race for three-year-olds held annually at Gulfstream Park in Hallandale Beach, North Miami. There are records indicating that Olive travelled with Willie on two separate occasions, in 1945 on a chartered flight from Mexico to Miami where they stayed at the exclusive Roney Plaza Hotel and in 1955, on the SS Argentina cruise ship from New York to Buenos Aires. The ad for the 38-day South American cruise with the Moore-McCormack Cruise Line that year lists stops in Barbados, Bahia, Rio de Janeiro, Sao Paulo, and Montevideo[45]. This implies that there may have been a romantic relationship between Olive and Willie at some point.
In 1956, Willie retired from racing (again) in his own name, turning his horses over to Blanche and Olive. The papers announced that he felt it was a young man’s game, but several other factors probably led to this decision. Willie had always been a rebel against the establishment. He was one of the boys, beloved by working-class fans. His win in 1938 with Bunty Lawless, followed by his 1940 Plate win with Willie the Kid, a horse he bred and leased to his friend Mildred Kane, made the little guy feel as if he too stood a chance against the wealthy owners who dominated the circuit[46].
Willie sat in the cheap seats, eschewing the club house, as he generally did not get on with the social elites. He had been at odds with most of the racing world for years. It started when he first bought a horse in 1933, and afterwards found out the seller had increased the price after learning Willie was the buyer. His work with the HPBA—securing larger purse winnings for owners—pitted him against track management, and his ongoing feud with Fred Orpen, owner of the Long Branch racetrack, was legendary—it had to do with disputed starting weights and unfair race tactics[47]. He faced a looming fight with the Ontario Racing Commission in the courts about the names of his horses, a result of the dispute with Orpen, and he sparred with John Mooney, the assistant managing director of the Ontario Jockey Club, over the perceived mishandling of stall allotments for his horses at the racetracks. Willie’s contrariness was on full display in 1959 when Queen Elizabeth attended the Queen’s Plate. E.P. Taylor, probably thinking he was doing him a favour, asked Willie if he wanted to meet her, but Willie scoffed, “no, I don’t want to!”[48] Morrissey, retired from the racing track, returned to the boxing ring as a fight manager. He continually denied any active participation in horse racing, but he still lingered in the background.
The extent to which Willie’s reputation affected those of Olive and Blanche at the racetracks is unclear, but they continued managing the stable of horses with Ed Hall as trainer. In 1957, Olive gave up her apartment at The Hotel Morrissey and moved to Morrissey’s farm in Etobicoke, along with Sam and his wife Ruth. That summer, Bunty Lawless died at age 21 and was buried on the farm. Olive was offered $17,500 for her horse O’Morrissey but refused (she eventually did sell the horse to Charles Mavety owner of Circle M Ranch in Kleinburg[49]). His manager, Al Greco, advertised O’Morrissey for stud in 1967. Maverty, a wealthy businessman, was the sole distributer of Hollywood films to all the movie houses in Ontario and his ranch was sometimes used as a movie studio for western-style movies[50]). Taking umbrage with the ongoing fight with the Ontario Racing Commission over the names of five of the horses in their stables, Olive declared that she would no longer train horses regardless of where they raced[51] and transferred the training of O’Morrissey to Ed Hall. It would appear she remained true to this statement.
Willie sold the farm in December 1958[52] to a developer who had plans to build 450 homes on the property. Suburbia was encroaching on three sides of the farm. The developer paid over $1 million for the property; Willie had bought it for a mere $32,000 five years prior[53]. It was an offer that was hard to refuse.
By that time Olive was managing 12 horses on her own farm in Woodbridge north of the Woodbine Racetrack[54], including George Hardy, which she saddled for the Queen’s Plate in 1959; he placed 18 out of 20. In December, the Supreme Court case decided against Willie and Blanche, upholding a regulation that allowed the Ontario Racing Commission to bar any horses they did not want on Ontario racetracks. As the registered owner of the challenged horses, Blanche stated that she intended to continue racing the horses until they were barred from the tracks[55]. However, Blanche, who had married in March 1959, seems to have exited the horse racing scene around this time.
Meanwhile, Olive and Willie were still working together. Willie had returned to the racetrack as owner/trainer to Gramp’s Pride in 1960, and a year later—in a role reversal—he trained Match Girl, a filly that Olive owned. Willy retired for the third and final time from horse racing in 1964, when he was 74 years old. Olive raced a filly named Teardrop Lane with some success in 1963-64 before selling her in 1965.
The last time Olive appeared in the Canada newspapers was at the 1969 Belmont Stakes in New York, not as a horse owner, but as a hostess to her niece, Sharon Armstrong (Oliver’s daughter) and her schoolgirl friends, to root for the Canadian colt, Majestic Prince. Shortly after this, Olive sold the farm and moved to Boston, Massachusetts, likely to take advantage of the greater number of horse races in the United States. Suffolk Downs was a thoroughbred racetrack in East Boston and the Narragansett Park racetrack was just 36 miles away.
Source: The Sun Transcript, Winthrop, Massachusetts, USA, June 19, 1975, p2.
It was the end of an era for the horse racing industry and the Armstrong family. A decline in the popularity of horse racing had several tracks close in the 1970s including Narragansett Park. Willie died on February 5, 1973 at age 83. Olive’s siblings were dying too, prematurely—her father had died at age 71, her mom, Eleanor at age 68. None of her three brothers made it past 64 years. Her sister Muriel died at 61 and Ada at age 68. Olive died on July 4, 1989 at 73 years of age. Blanche, 6 years younger than Olive, died at age 74, on May 8, 1996, and her twin sister Mildred, died one year later on June 17, 1997. One brother, Roy, outlived his entire family (as per Mildred’s obituary), however his date of death is unknown.
Aside from the usual obituary, Olive’s death was acknowledged in a small Toronto Star article. Without a Queen’s Plate win however, many forgot her involvement in the sport, even news reporters. Toronto Star sportswriter Neil MacCarl wrote an article in June 1976 about horse trainer Penny Ryan titled “Ryan, first woman saddling for Plate”. Leave it to the woman, Penny Ryan, to diplomatically school the reporter saying, “I just assumed Olive Armstrong might have saddled a horse for Willie Morrissey”. Do your homework, dude.
We might excuse him, as it had been a long 23 years since a woman, Olive, had saddled a horse for the Plate. In 1990, Globe and Mail reporter Bob Johns claimed that, until 1960, not a single woman was licensed in Ontario as a horse trainer. Wrong. In a letter to the editor[56], Louis E. Cauz, retired sports journalist, corrected the record naming three women licensed in the 1950s—Wilma Kennedy, Mamie Mezen and Olive Armstrong.
If Olive and Blanche’s mark on horse racing failed to gain keep the attention of those who covered the sport, it’s hardly surprising that their achievements have been largely forgotten in the intervening decades. Against all odds—remember this was the 1950s—Olive and Blanche successfully competed in an industry dominated by wealthy men. While their backer, Willie Morrissey, was also wealthy, this does not diminish their accomplishments. It could not have been easy making their mark playing a man’s game. One might argue that if more men had championed women and allowed them their due accolades, we would know more stories of accomplished women. Too often, women’s contributions were devalued or diminished, and no one put pen to paper to capture their successes (or their failures). In horse racing, few women made it to the top (see below for a list of women’s sparing accomplishments in the sport). I hope Olive and Blanche Armstrong’s story helps revive the achievement of these two remarkable competitors, who were ahead of their time.
As for the filly, Stole The Ring, if she had won the race that day, the archives would have the photographs that captured the post-win celebrations, showing Blanche and Olive receiving the coveted gold trophy and the 50 guineas prize, along with her breeder, Willie Morrisey. But, without that crowning achievement, those photos do not exist. Jim Proudfoot’s prediction that the 1958 Plate would always be known as Stole The Ring’s Plate was wrong and jockey Johnny Longden’s prophecy turned out to be true, but not in the way he meant—they never did beat the filly again because she was retired shortly after her Queen’s Plate run in November 1958[57],[58].
Let’s face it, women have not made broad steps in the sport of horse racing:
Endnotes
[1] The lakeside Woodbine racetrack in Toronto’s east end at the foot of Woodbine Avenue was supplanted as the host of the plate in 1957.
[2] Jennings, Cec. Horse’s owner said neigh to the Queen. Jennings, The Globe and Mail, Jun 25, 1983: D12.
[3] Toronto Daily Star, May 31, 1958: 37.
[4] Plate Trials Are Features at New Woodbine Today. The Globe and Mail, Jun 2, 1958: 23.
[5] Toronto Daily Star, Jun 3, 1958: 14.
[6] The court case would ultimately end up at the Supreme Court of Canada, where William F. Morrissey and C. Blanche Armstrong lost their case. It was a hollow victory for the OJC since most of the named horses were either retired or dead.
[7] Perlove, Joe. Stole The Ring Plus Entourage Checks Into New Woodbine, Toronto Daily Star, Mar 17, 1958: 18.
[8] Toronto Daily Star, 12 Oct 1957: 31.
[9] Toronto Daily Star, June 1958: 16.
[10] Toronto Telegram, Jun 9, 1958: 10.
[11] Toronto Daily Star, Jun 9, 1958: 22.
[12] All the dates and timelines in this paragraph come from a review of the Toronto City Directories 1937-1964.
[13] The Kingston Whig-Standard, Kingston, Ontario, May 29, 1953: 11.
[14] Sam A. Armstrong was a witness signature on the offer to purchase agreement between Morrissey and the developer in December 1958 with respect to the sale of the William Morrissey farm in Etobicoke, implying that the brothers, Sam and Oliver, probably helped out in all manner of things both at the hotel and then later on the farm.
[15] The Toronto Star, May 28, 1957: 17.
[16] Toronto Telegram, Nov 19, 1959: 33.
[17] Cauz, Louis. The Plate, A Royal Tradition. Deneau Publishers, Toronto, 1984: 181.
[18] Cauz, Louis. The Plate: 181.
[19] The Kingston-Whig-Standard, May 29, 1953: 11.
[20] The Chronicle Sporting Journal, Dec 14, 1951, Vol 15, Issue 16: 18
[21] The Globe and Mail, Mar 18, 1950: 18.
[22] Toronto Telegram, Nov 19, 1959: 33.
[23] The Toronto Star, Jul 6, 1996: 11.
[24] Information from telephone conversation with Linda Rainey, Canadian Horse Racing Hall of Fame, Feb 5, 2024.
[25] The Globe and Mail, Aug 22, 1939: 3.
[26] Ontario Land Registry (ONLand), Metro Toronto LRO 80, Etobicoke Township, Concession 3, Lot 13.
[27] $32,000 Morrissey Farm Home of Bunty Lawless Now Sold for $1,075,000. Toronto Daily Star, Apr 4, 1956: 1, 3.
[28] Canada, Voters Lists, 1935-1980, Ontario, Electoral District York West, 1957, Image #20273, Ancestry.ca published 2012-10-01.
[29] Calgary Herald, Apr 29, 1953: 38.
[30] The Globe and Mail, May 23, 1952: 16 and Toronto Daily Star, May 23, 1952: 22
[31] The Globe and Mail, Jun 3, 1952: 16
[32] The Globe and Mail, Jun 19, 1952: 18
[33] The Globe and Mail, Sep 6, 1952: 22 and Toronto Daily Star, Sep 6, 1952: 11
[34] The Intelligencer (Belleville), May 1, 1953: 10
[35] The Kingston-Whig-Standard, May 29, 1953: 11.
[36] Cauz, Louis. The Plate: 215.
[37] The Globe and Mail, June 9, 1953: 18.
[38] The Globe and Mail, Aug 23, 1953: 22
[39] The Globe and Mail, Sep 14, 1953: 24.
[40] The Globe and Mail, Sep 21, 1953: 22.
[41] The Globe and Mail, Sep 24, 1953: 18.
[42] The Globe and Mail, Aug 19, 1954: 16.
[43] The Globe and Mail, Oct 8, 1954: 24.
[44] The Globe and Mail, Nov 5, 1954: 20.
[45] From https://www.ebay.ca/itm/175868658157, retrieved Feb 11, 2024.
[46] Cauz, Louis. The Plate: 174.
[47] Morrissey and Orpen got into a bicker over the weights ascribed to Casa Camara and Hi Bunty, two of Morrissey’s horses, for the 1947 Cup and Saucer. They came in first and second anyway. The following week the Diamond Ring race was to be held at Long Branch. Orpen created a special race, called the Silver Knife, of which any 2-year-olds could race except those that had come in 1st or 2nd in the Cup and Saucer. All other entrants chose to compete in the Silver Knife, leaving Morrissey’s colts with no competitors for the Diamond Ring. The horses were walk-overs, but Morrissey refused to accept the award.
[48] Jennings, Cec. Horse’s owner said neigh to the Queen: Bunty Lawless won Queen’s Plate and that was as close as Willie Morrissey got to royalty. The Globe and Mail, Jun 25, 1983: D12.
[49] The Canadian Horse Stallion Directory. The Canadian Horse Magazine, Feb 1967: 93.
[50] Currie, Ted. The Mysterious Photo Collection From The Circle M Ranch Of Kleinburg; Do You Know This Cowboy? Wednesday, June 10, 2015, gravehurstmuskoka.blogspot.com.
[51] Will Horses be Banned, It’s Up to Commission or Jockey Club Now, The Globe and Mail, May 30, 1957: 35.
[52] Offer to Purchase, ONLand, Historical Books, Metro Toronto, LRO 80, Document EB209364.
[53] $32,000 Morrissey Farm Home of Bunty Lawless Now Sold for $1,075,000. Toronto Daily Star, Apr 4, 1956: 1, 3.
[54] Ontario Land Registry (ONLand), York County, LRO 65, Vaughan Township, Concession 8, W ½ Lot 9.
[55] Winnipeg Free Press, 2 Dec 1959: 26.
[56] Letters to Sports Editor, Globe and Mail, Oct 19, 1990: D12.
[57] Illness Forces Stole the Ring To Quit Racing, The Globe and Mail, Nov 1, 1958: 25.
[58] Le Nouvelliste (Trois-Rivieres), 8 Novembre 1958 : 17.
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