Laurie Silvera, the Jamaican gentleman

On  the backside of Woodbine Racetrack one balmy summer morning, Laurie Silvera chugged up a gentle slope in his SUV, and parked it to watch a horse work. Classical music filled the cab.
It’s not what you’d expect from a horse trainer who has spent the 85 years of his life on dusty backstretches and under barn roofs ridden by pigeons.
“The music they play today, I find no joy in it,” said Silvera, from under his signature Stetson. “But then again, I remember my parents saying: ‘I don’t understand what rubbish these children are listening to.’”
Rubbish like Frank Sinatra? Yes, quoth the backstretch sage.
He believes the greatest song ever written is “Stranger in Paradise.”
“Take my hand,” goes the Tony Bennett song.
“I’m a stranger in Paradise.
All lost in a wonderland.
If I stand starry eyed
That’s a danger in Paradise.”
Silvera’s paradise for more than 40 years has been the backstretch of Woodbine Racetrack, where he has spent much of his time since he landed in Canada in 1974, after leaving his birthplace of Jamaica. He speaks with a Jamaican lilt. His home near Guelph, Ont., is filled with the sound.
He has no intention of quitting his job. “Fortunately in racing, if your eyesight is in order and your mind is in order, you can do as good a job as a 20-year-old with all the physical attributes that you would like,” he said.
Time and experience are Silvera’s trump cards. “If your mental attributes remain with you, you get better as you get older,” he said. “Let’s face it: training is a guessing game. Until you can talk to horses, it can’t be a science. But it’s a guessing game based on educated guesses. Experience makes the difference.”
He looks forward more than he looks backward. Last fall, he bought three yearlings, one of them a colt by Exhi out of T.P.’s Wit, for $22,000. He’s a half-brother to Julie’s Witt (winner of the Ontario Damsel and the Passing Mood Stakes at Woodbine) and Mighty Quinn (winner of the Vice Regent, Bold Ruckus and Frost King Stakes). He’s named the colt Wit o’ Windsor, after a good horse that his father, Owen had, while Laurie was growing up in Jamaica. The original Wit o’ Windsor (translation: the Smart Alec of Windsor) was a British-bred horse that his father imported and he raced in the top classes at Caymanas Park. The Jamaican theme keeps popping up in Silvera’s bailiwick.
Caymanas Park, a 1/18-mile track, opened in 1959 and before that, there was Knutsford Park in Kingston. Currently, Silvera has a horse racing at Woodbine called Knutsford Park.
Don’t ask the niggly details of his previous horses and his past life. He doesn’t remember them. His first winner in Jamaica as a trainer was with a mare called Silver Light, owned by his first client, Barry Rose. Silvera remembers her as a good filly. Beyond that, nada.
“I don’t remember too much,” he said. “I’m not one that contemplates yesterday that much. I’m a today and tomorrow person.
“I don’t ponder the past at all. There is nothing you can do about the past. That is part of my makeup. I don’t dwell on the past.  In this game, what you did yesterday is soon forgotten.”
But his yesterday is fascinating.
Silvera’s yesterday
Silvera’s ancestors came from Spain, via England.  Silvera believes they were Jewish and escaped the country during the Spanish Inquisition, which ordered Jews and Muslims to convert to Catholicism or leave the country in 1492. Silvera’s forbears headed for England and then in 1745, two adventurous Silvera brothers settled in Jamaica, a British colony.
They became farmers, establishing a beautiful banana plantation in Jamaica. Large enough, by all accounts. “For anybody coming from England, the land was there for the taking,” Silvera said. His father, Owen, continued the tradition.
Horses were a way of life in Jamaica. The first industry in Jamaica was horse breeding and sales. The majority of horses used by Cortez to conquer Mexico were bred in Jamaica. Transportation was by buggy. Horseback riding was a pleasure sport. It’s not surprising that Silvera’s father found his way into training thoroughbred race horses.
The racetracks in Jamaica never had the financial wherewithal to equal those in Canada or the United States, but racing was a revered pursuit. “The joy of racing far surpasses that of Canada,” Silvera said. “The general population in Jamaica knows all about what is going on in racing. It’s covered in the newspapers on a daily basis.” Racing got a large section of the sports page – and it still does.
Sometimes top British jockeys, like Lester Piggott and Sir Gordon Richards would ride in Jamaica. They were treated like royalty. Piggott has in the past ridden for Silvera. “He was somewhat hard of hearing,” Silvera recalled. Piggott would spend December and part of January in Jamaica.
Silvera’s father was one of the leading trainers in Jamaica and was well known throughout the country. Back in the 1940s, he trained a horse called “Brown Bomber,” described in the Jamaica press as “great and invincible.” His most intense tangles were with a horse called Jetsam in Trinidad.
Silvera doesn’t know a time when he didn’t sidle up to a racehorse. “I grew up in a racing stable,” he said. He galloped horses for his father.
At age 18, Silvera wrote the senior Cambridge matriculation exams that signalled the end of high school. The exam was sent to England to be scored. Silvera passed.

Silvera played on a cricket team in Jamaica. He’s the one with the wavy hair, back row, fifth from the left.
Photo courtesy of Laurie Silvera

Career established
It wasn’t a stretch for Silvera to start training horses, but he didn’t take out his training licence until he was 29 years old. His mother, Angele – who had an eye for a good horse but stayed away from the barns – wanted him to become a veterinarian. But Silvera started training horses for Rose, won some races and people began to take a second look at the tall young man. “All of a sudden, you have a barn full of horses,” he said.
He trained about 200 winners in Jamaica and was leading trainer there five times between 1960 and 1970. There were no stabling facilities at Caymanas, so the family would walk or ride the horses three miles to the track.
One of Silvera’s best horses was a tiny filly (14.2 hands high) called Bonnie Blue Flag, pretty, tough and wiry, known to carry huge imposts. She used to go long. She became one of the most revered horses in Jamaica.

Silvera, left, with the original Bonnie BlueFlag
Photo courtesy of Laurie Silvera

Years later in Barbados, Silvera spotted another filly that almost took his breath away: She looked exactly like Bonnie Blue Flag with her chestnut coat and blaze. So Silvera named her Bonnie Blue Flag, too, and she became the top 2-year-old in Barbados. With Silvera, what goes around often comes around.

Silvera with his next Bonnie Blue Flag, champion 2-year-old in 1994 in Barbados
Photo courtesy of Laurie Silvera

Now there is a race in Jamaica named after Silvera’s great fillies: The Bonnie Blue Flag Trophy. Last year, it was won by All Correct, a horse owned by Silvera’s nephew Raymond Rousseau. Shane Ellis rode him.
In 1965, Silvera ended up in Richmond, Va., to visit one of his father’s clients, Richard Reynolds, a big mining boss, who invited him to spend a week with his family. But it was March and it was cold for a Jamaican. Silvera went looking for a hat, and didn’t find one he liked until he spotted a 10-gallon Stetson. He bought it and never took it off, he said.
Now, he doesn’t take it off, because underneath it all, he’s bald, and if he doffed it, nobody would recognize him. “I was born bald,” Silvera says. Over the past 50 years, Silvera estimates he’s owned about 100 Stetsons.  It’s now his trademark.

The man with the hat.
Photo courtesy of Laurie Silvera

While in Jamaica, Silvera met Clive Brooks, who owned several supermarkets and retail outlets in the country. Silvera trained the second horse Brooks ever owned after they met in 1961. The name of their first horse together? Jesse James, after the American outlaw, gang leader, bank robber, murderer and folk “hero.”
“We had a lot of fun with him,” Brooks said of the horse. And then things, as Brooks describes it,” just exploded.”
At age 34, Brooks sold all of his commercial holdings and retired. At first blush, it seemed like a good idea. At second blush, he realized he needed to do something. He suggested to Silvera that he buy a farm and get into the horse business. Silvera liked the idea.
They called their partnership and their farm “Silverbrook” a combination of both of their names. “He wanted to call it the other way around,” Brooks joked. “But that didn’t make any sense.”
The two of them started to go to the United States to buy, import horses to Jamaica and then sell them. Their little farm, on about 100 acres, was home to some horses they bred, too. On their buying trips, they would move around, but their first stop together was Charles Town, Va., a small town of about 5,000 in a rather remote area of the state.
“I can’t tell you how much I enjoyed that place,” Brooks said. “It was a real backwoods sort of operation.” The town found it necessary to enact a bylaw decreeing it unlawful to keep unlicensed, abandoned, junked cars on public or private property for any longer than 10 days. The terrain was rugged. Mountain culture reigned.
“But the guys were fun to be around,” Brooks said. “We bought quite a few horses in Charles Town.”
They would ship them to Florida, then to Jamaica. In most cases, they sold the majority of them before they even left the quarantine station. “We just told people we had horses and they came to look at them, and we sold most of them,” Brooks said.
There was a decent profit margin involved, he said. These horses were very cheap. After all, the standard of racing in Jamaica didn’t demand more. Brooks remembers the first place he went to in Ocala – in the days before OBS – attending a horse auction sale that was on the site of a cattle auction. It wasn’t high brow. “I think at that sale, I bought the sale topper,” he said proudly, with a twinkle. Price? $3,500.
“It was something ridiculous,” Brooks said. Silvera was savvy enough to realize that there wasn’t a lot of money in training horses in Jamaica. Trading horses worked better.
“We messed around a lot in Ocala,” Brooks said.  “I got to know a lot of the guys down there. So we’d visit quite often. We both liked it there for a long time.” He and Silvera had adventures together. They laughed a lot.
As a leading horse trainer, Silvera gained celebrity status in Jamaica. “You are inclined to get preferential treatment,” Silvera said. Once, when he flew into Kingston, and needed a taxi to take him home to Spanishtown – three-quarters of an hour away – the driver dropped him off and said: “No charge.” And there was nothing unusual about it. Racing was part of Jamaica’s culture.
But while life in Jamaica seemed idyllic in one way, it wasn’t in another.  “Jamaica became a little too hostile for our liking,” Silvera said. He was married, with six children from age seven (Arthur Silvera) to teenagers. “We decided the future for them in Jamaica was not particularly accommodating.”
There was a lot of crime. The rule of law was ignored. Bullets would whistle past ears. One morning, Silvera was standing on the Caymanas track when a man came rushing toward him. “Help me,” he cried.
“Mr. Laurie, I beg you.”
The man ran behind Silvera, who found himself staring down the barrel of a revolver. “And I was between the man and the revolver,” he said.
Silvera did the only reasonable thing that he could in those circumstances. He legged it, as fast as his feet would carry him. “I left at such a speed that I would have made Usain Bolt look like his grandmother,” he said.
Another morning, bullets screamed overhead at the track. “Two rival political gangs, I guess,” Silvera said. “When you are in the middle of that, it is not fun.”
Gradually, Silvera reduced his string of between 30 to 40 horses and both he and Brooks left for Canada where they all had close family already. Silvera bought a home near Toronto. Brooks looked around for a business to run and couldn’t find one that satisfied him right away.
When Silvera arrived in Canada, he told Brooks that he was finished with horse racing, that he had to try something new. He’d done it long enough.
“We were sort of at loose ends and didn’t know what we were going to do,” Brooks said. But he found the ticket when he took his young kids bowling. “I had never seen a bowling centre before in my life,” he said. “I looked around and thought: ‘This looks like something worth doing.’”
Brooks bought some land at Walker’s Line in Burlington, Ont. and had a 36-lane alley built, called Burlington Bowl.  “In those days, Walkers Line was like you were out in the sticks,” Brooks said. “There was nothing around. People told me I was crazy. What am I doing out there? But it did very well.” He expanded it to 48 lanes.
Both he and Silvera owned the bowling alley, although Silvera says it wasn’t his game.  They sold it, then build another one in Hamilton, Ont., called Hamilton Mountain Bowl. At 60 lanes, it was the largest in Canada and had the latest automatic scoring technology. They owned it together for 30 years until it was sold a few years ago. Silvera’s wife, Claudia, worked at the bowling alley for years.
But about a year into Silvera’s new experiment with bowling alleys, Brooks encouraged him to go back to training horses. “Let me tell you something,” Brooks said. “That’s what you’re going to do because that’s what you know and that’s what you enjoy.”
Brooks talked him into going to a horse sale and convinced him to buy a horse for Silverbrook. The horse, Dashing Young Man, was a modest investment at $7,000 to $8,000. Silvera took out a trainer’s licence in 1975. Dashing Young Man didn’t disappoint, giving Silvera his first win in Canada, well enough that, as Brooks says, that one thing led to another and soon Silverbrook was in full swing.

Silvera’s first win in Canada.
Michael Burns Photo

And soon Silvera was in full swing too. He proved to be a wizard at picking out precocious horses with early speed. He thrives on picking out young horses and developing them into something.  He won three straight Greenwood spring titles from 1989 to 2001, where sprints were king. His stable stars?
Silverbrook’s first stakes winner was George Dinkle, a son of Wrinkle Dinkle, that Silvera claimed ($32,000) and then turned him into a stakes winner (Connaught Cup). In the winner’s enclosure, Dinkle rose up on his hind legs, perhaps protesting his name, perhaps celebrating his accomplishment. A photograph of this memorable moment won somebody an Eclipse Award.
Silvera picked Rustic Light out of a sale for $28,000 for Silverbrook and the horse won the $500,000 Illinois Derby in 1993, leading all the way in the slop. Rustic Light placed in other major sprint races in Canada and won almost $600,000.
And who can forget Demaloot Demashoot? This fan favourite was a track-record setter whose victories all came at six furlongs or less, all good enough to win $574,825 in his career, winning stakes all over North America from age two to six. At one point, he landed in Team Valor’s barn, and finished fifth in the Breeders’ Cup Sprint in 1993.
Silvera’s Free At Last was a Sovereign Award as champion 2-year-old colt in Canada in 1991, after winning the Summer Stakes.
The trainer also picked out a colt called Solo Guy at a sale in Miami for $32,000 for one of his early clients, Gord Hall. It was an astute pick. Solo Guy was a champion sprinter, winning the Victoria Stakes as a 2-year-old. As a 3-year-old, he won the Nearctic Stakes and also took the Highlander too. Solo Guy went to California and won a graded stakes there, too.
Silvera took a chance on buying a yearling filly from the first crop of Storm Cat – before he’d proven himself at stud  – and paid $35,000 for November Snow.  “She was out of a good producing mare,” Silvera said. The Storm Cats would get more expensive later.  By 2005, one of his yearlings brought $9.7-million at Keeneland. And his stud fee climbed to $500,000.

Silvera with Clive Brooks (second from left) after a November Snow victory at Woodbine.
Michael Burns photo

In the beginning, Silvera wasn’t overly impressed with this filly, which finished fourth in her first start. He ran her back in the My Dear Stakes. The filly had figured it out by this time and came from behind to win going away to become Storm Cat’s first stakes winner. She paid $100 to win.
After that, Earle Mack bought her. As a 3-year-old she won the Alabama and Test Stakes at Saratoga, was runner-up in the Eclipse voting for 3-year-old filly, and was eventually sold for $1.1-million as a broodmare.
For eight seasons from 2001 to 2011, horses trained by Silvera earned more than $1-million. During that time, Silvera scored with Ariana D. in the Bessarabian Stakes, closing from last at 18 to 1 to win, and in the Avowal the next year. She also hit the board in four of five graded stakes she contested at Woodbine and Presque Ile.

Silvera, still winning after all these years. With Bob’s Ring and Emile Ramsammy April 25, 2010.
Michael Burns photo

In 2009, Silvera won his 900^th race with Dublin Lane, and it took him five years to win his 1,000^th race, with his splendid gray Sorry About That.
In the meantime, Silvera always gave a hand up. Several years in a row, he’d pick out a yearling, keep 50 per cent of it for himself, then let grooms in his stable own parts of the other 50 percent. “A couple of times, we did really well,” he said.
Woodbine groom Larry Harvey Brenton knew Silvera as a kid growing up in Jamaica and came to the Woodbine backstretch in 1989. Silvera once picked out a yearling for him for $5,000. The horse won some races and they sold it for $50,000. “He was the best,” Brenton said of Silvera. “He would help me out any way he can. He’s one of the greatest trainers on the grounds.”
Silvera doesn’t think it is any more difficult to buy yearlings than it has ever been. “What is tough is to select a good horse,” he said. “I believe I am able to do this better than most. It stems from experience and I look at horses critically from the get-go. There are some common denominators in good horses. ’
Brooks eventually got out of the racing business during the early 1990s, so now Silverbrook includes Silvera and Brooks’ two sons, Phillip and Cary, who train a few horses, too. “I call him uncle,” Phillip says. “I’ve known him since I was born. He’s like a father to me.”
Some call him Sir Laurie.
At age 85, Silvera still oversees a stable of as many as 18. In general, training horses has given Silvera the experience of a lifetime. “Up to this day, I enjoy it to an extent you would not imagine,” he said.
“When I’m able to drive in here and perform the day to day things, I’ll be here until I’m unable.”