Make no mistake about it, acquiring Sky Promise was pretty much a shot in the dark.

But then it is horse racing: a sport built on chance, speculation and rearing back and throwing the old Hail Mary up into the gathering clouds and seeing what comes down other than thin, cold rain.

Still, when trainer Robertino Diodoro filled out the $40,000 claim slip on June 30 at Churchill Downs he really had no idea what he was buying for his Alberta clients Tim Rollingson, Rick and Clayton Wiest and Norman Tremblay.

“No doubt,” said Diodoro of the three-year-old who would go on to be the first winner of the Western Canadian Triple Crown: the Manitoba Derby, Canadian Derby and B.C. Derby. “We were really rolling the dice with this one.

“Sky Promise had been running almost exclusively on turf. I had no idea if he could run on dirt and that’s what we were looking for — a horse that could compete in those three Western Canadian races which were all on dirt.


“I was actually kind of scared that we would take him to Winnipeg, that he wouldn’t run a lick on the dirt and we’d wind up having to take him back to Canterbury Downs and have him run on the grass again.

“To be honest, I wasn’t sold.”

But someone else was: Arkansas-based bloodstock agent Cody Autrey.

“Cody was the guy. He was the one who picked him out,” said Diodoro. “He kept telling me ‘This horse will run on dirt.’

“I’d say, ‘but…’ and Cody would say the same thing: ‘This horse will run on dirt.’

“He was sure right.”

Was he ever. Sky Promise, as is his wont, came from far behind to win the $75,000 mile and an eighth Manitoba Derby at Winnipeg’s Assiniboia Downs on Aug. 6 by seven-and-a-half lengths, overcame dreadfully pedestrian early fractions to win the mile and three-eighths Aug. 25 $200,000 Canadian Derby at Edmonton’s Northlands Park and then completed the triple getting up just in time to win the mile and an eighth $150,000 B.C. Derby at Vancouver’s Hastings Park on Sept. 8.

In those three races, Sky Promise won $248,400 and clearly stamped himself as one of the heavy favourites for a Sovereign Award as the nation’s top 3-year-old colt or gelding.

“We took a gamble and it sure paid off,” Diodoro said of the big, chiseled dark bay with a long white blaze that starts on his forehead and trickles all the way to his lips, who only had one win in 15 appearances before he got his hands on him.


“I had a feeling about Sky Promise,” said Autrey, a former trainer.

“He only ran two starts on dirt to begin his career and he ran pretty well in both of them — galloping out strong. And his numbers were pretty good. Then they stretched him out to two turns and put him on grass. That’s when he got good,” said Autrey believing that running him long improved the colt more than the switch to grass.

“He was kind of a grinder. His running style was that he drops back and then makes a big run. I like those kind of horses on dirt better than on grass. And I liked his pedigree.”

Diodoro and his Alberta owners also had reason to trust Autrey. After all, it was Autrey who pointed Diodoro, the Wiests, Rollingson and Randy Howg in the direction of Chief Know It All last year and while the Edmonton result is still in the courts, Chief Know It All crossed the finish line on top in the Canadian Derby and then went on to win the B.C. Derby, as well.

“You have to give the owners a lot of credit for that one because they claimed Chief Know It All for $100,000,” said Autrey. “He’s still the only horse that has ever been claimed for $100,000 at Churchill Downs.”

As for Sky Promise, Diodoro tried to claim the son of Sky Mesa for $30,000 three weeks before they got him for $40,000 but got out shook.

“When Sky Promise resurfaced for $40,000 I told Robertino that we had to go back in,” said Autrey. “I believed that even if he couldn’t run on dirt he would still be worth $40,000 on the grass.

“We took a shot and it turned out very well.

“My job is to find the horses and it’s up to Robertino to train them, which he does very, very well.”

Rollingson really liked Sky Promise too.

“We had just bought Hyndford, who finished seventh in the Canadian Derby, privately for $140,000 and the other three guys weren’t too sure about claiming another one,” said Rollingson, a Lethbridge, AB dentist.

“I kind of forced their hands. I was being stubborn. I had watched all of his races and if the others weren’t prepared to claim Sky Promise I was willing to claim him on my own even though $40,000 is a lot of money to me.

“That’s how I ended up getting 50 per cent of Sky Promise instead of just a quarter interest,” said Rollingson, who rented a bus and took 15 people to Winnipeg including his four children, son-in-law, parents, and his brother. To get to Edmonton the large group travelled together in five vehicles. This time my sister also came.


“We flew to Vancouver. By then we figured we could afford it.

“Sky Promise, who brought our family together, far exceeded all expectations. To win all three of the Western Canadian Derbies is really quite remarkable.”

This year’s Canadian Derby marked the fourth time Diodoro has won that race having also come out on top with Broadway Empire in 2013, who would also go on to win the Oklahoma Derby, and Edison in 2014.”

Alberta’s perennial top jockey Rico Walcott rode all four of them and was also aboard for the Oklahoma Derby and the two B.C. Derbies.

“I’d really like to see Rico go somewhere outside of Alberta because I know he can ride with anyone. He’s young, smart, patient… Nothing seems to rattle him,” Diodoro said.

The trainer clearly recalls being vexed and concerned watching the Canadian Derby unfold when the first quarter went in :25 4/5, half a mile in :51 and three-quarters in 1:15 4/5 and Sky Promise only had one horse headed in the field of nine.

“I was worried,” said Diodoro.

Walcott wasn’t.

“I had horse from the start. He was even more on the bit then he was in Winnipeg,” said Walcott, who, because of the slow pace, had Sky Promise on the move early with more than half a mile still left to run.

“I got him to the outside, tipped him out and he fired.

“Robertino didn’t give me any instructions. So I rode him the same way as I did in Winnipeg.”

In Vancouver, Diodoro was worried again.

“When Weekend Wizard cleared halfway around the final turn and opened up two-and-a-half lengths, I thought we were in trouble. I thought we were done. I was thinking well at least we’ll get second.”


But Sky Promise was just warming up, his big stride cutting through the ground almost effortlessly.

“Sky Promise just kept coming and coming,” said Diodoro. “Down the stretch I said to myself ‘Holy crap; he can win this.’”

He did, of course which is something Diodoro has always done a lot of especially since leaving Alberta where he started his career and moved to the U.S. six years ago.

With 135 horses spread across the continent at press time Diodoro was the third winningest trainer in all of North America and 20th in purses won.

“For some reason Robertino doesn’t seem to get the credit in his own country that he does in the U.S.,” said Rollingson.

“I know that if I was just starting out as an owner Robertino would be the guy I’d want training my horses.

“The man is a horse racing genius. He’s going to win Breeders’ Cup races; he’s going to win the Kentucky Derby.

“He gets more out of horses than anyone else.

“To win three Derbies in 33 days at those distances with Sky Promise is incredible.

“He also keeps me on as an owner because he makes everyone feel wanted. He cares about me. He cares about my family and he cares about my horses.”

With Northlands Park closing its doors after 118 years of horse racing and a new track, Century Mile, opening next spring next door to the Edmonton International Airport, the Canadian Derby was the last thoroughbred race ever at Northlands.

“I won my first race here as a trainer. To win the last is special. There’s a lot of history,” said Diodoro, who recently saddled his 2,000th winner in Saratoga, NY.


Diodoro, 44, started training thoroughbreds when he was 18.

“When I told my mom what I wanted to do she just about had a fit. She thought I was nuts. The first thing she asked me was what horses I was going to train. I told her I had leased two horses from Gene White,” he said of the late former training giant.

“I got 80 per cent of what the horse’s won; Gene got the other 20 per cent. It sounded like a good deal at the time. The math, however, didn’t exactly work. Eighty per cent of nothing is still nothing. I raced those horses at Trout Springs,” he said of a small oval near Calgary. “There was just no money to be made. The purses were about $600. At the end of that summer I had to borrow money off my mom to pay the blacksmith.

“My mom’s dad, Jim Dorman, used to train a few horses — one or two; three or four at the most — so it wasn’t like getting into horse racing came out of the blue. And my dad, Tino, used to help Jim out in the mornings before he went to work. I loved going with them to the track and that hasn’t changed.

“I still love the winning. Whether it’s with a $3,000 claimer at Lethbridge or a hundred grand stake at Santa Anita. It’s the most addicting thing there is. The biggest rush ever.

“I played sports all of my life. I played hockey until I was 21. I played basketball. Playing in tournaments used to be such a big rush. But nothing compares to winning a horse race.


“We all get frustrated. Everybody in this sport has had their hearts broken. You get depressed. But I can’t imagine doing anything else.

“Every day I get up in the morning, jump out of my vehicle and walk into a barn full of horses.

“How does it get better than that?”

If everything unfolds the way he anticipates, Sky Promise’s next start will be the Nov. 21 Zia Park Derby in New Mexico.

“He’s getting bigger; he’s getting stronger,” said Diodoro. “He’s really just beginning to grow into himself.

“Some horses, like some humans, are late maturing and I think that’s the case with Sky Promise too.

“Whatever happens we’ve all had a blast with this horse.”