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Optimism and opportunity

Story and photo by: Hayley Morrison
“It almost didn’t happen, but I pursued it and had a good end to the year,” said Santino Di Paola, reflecting on the 2017 racing meet and his first official year as a trainer at Woodbine Racetrack.
Di Paola, who just turned 24, may be young when it comes to training racehorses, but his family has been in the horse racing industry for the last four decades.
“We breed our own and raise our own,” noted Di Paola. At our old farm in Markham, we had a five-eights of a mile track, so we would actually leg them up before they would go to our trainer at the time, which I think was Laurie Silvera. So I learned that way and caught the bug when I was 16 – just because I would gallop some and then my cousin Mike would gallop and I think we had about eight in training at the farm. It was cool to see them go out to the track and train, come back and get fitter and stronger. Then you would see them go in (to the racetrack), and they would win allowance races or whatever and it’s just cool to see.”
Naturally, the next transition for Di Paola would’ve been to work for his family’s racing stable, York Tech Racing. However, a certain horse influenced his decision to divert routes before entering the racing oval. 
“It’s a funny story,” he recalled. “Back in 2009 going into 2010 we had a horse named D’s Wando, who was one of the favourites for The Queen’s Plate. I started a blog because he was like the buzz horse, I had the in with the pictures and it did alright. It got enough views and people followed it.”
In 2012, Di Paola, struck by the photography bug, attended Georgian College in Barrie where he took a variety of courses, including videography, marketing, coding and web design. Once he graduated from school in 2014, he applied his media skill-set to the sport he loves. Not only spearheading his own horse racing site, CHRTB (Canadian Horse Racing Thoroughbred), but also developing a show for Woodbine known as Road to the Plate.
As much as he loved media production, Di Paola still had the itch to make it as a trainer. In 2015, he began working at Woodbine as a groom, cleaning stalls, checking horses legs, and getting horses ready for training. He vividly remembers being an early bird for his job.
“We got there super early, we got there way earlier than we had to,” said Di Paola who still turns in a seven-day work week at the track as well as working at the family farm in Schomberg, Ont. “I think we were there at 4 o’clock every morning – (laughing) that died out within a month or two.”
For the past three years, Di Paola has been learning the ropes and steadily gaining the knowledge he needed to succeed as a trainer. Along the way he’s received advice from various Woodbine-based trainers.
“I’ve talked to a bunch of different trainers and they’ve helped a lot - Paul Buttigieg, Josie and Mike De Paulo.”
Another seasoned Woodbine trainer that offered the young horseman advice was Sid Attard. 
“He was just very open and he told me, ‘you’ve got to let your horses run, do this and do that, make sure your gallop boy is doing this…’ I listened and it all started to click and I started to build on that with myself,” said Di Paola, who believes Attard’s advice did play a role in his success towards the end of last year.
“They were continuously hitting the board throughout the year,” he continued. “I think we had 16 fourths. But near the end of the year everything was kind of just clicking and it made sense with what Sid said and it worked.”
In his first year as a full-fledged trainer Di Paola recorded two wins and six second-place finishes from 76 starters, banking just over $130,000 for the 2017 meet.
The two wins were delivered by a couple of Di Paola’s homebreds, D’s Double Eagle and D’s Ben. While both horses have provided the family with success, D’s Ben has a special place in Di Paola’s heart.
“We actually named him after my dog that passed away,” said Di Paola of the dark bay gelding, whose sire also had a hand in his earlier career choices. “It was a couple of years ago. He was 15, he was our first pet and it was a hard loss for us.
“It was actually D’s Wando’s first foal. So we have the stallion and the mare. It’s cool; it took awhile for him to figure things out. I think it was six or seven starts when he broke his maiden.”
D’s Ben finally broke his maiden on December 10, 2017, still a special moment for Di Paola.
“I actually ended up in the hospital after the win,” he remembered. “I did not make the winner’s circle. I actually collapsed and couldn’t breathe. Actually, with my legs, I had no leg function at all. I then blacked out a couple of times.”
While D’s Double Eagle marked the first win for Di Paola, winning an $8,000 claimer in November, D’s Ben brought in a total of $54,780 in purse money on the last race day of the year.  
In light of last year’s results, Di Paola is coming back with hopes of improving upon his win record.
“I mean you don’t think it’s that tough to do, but it really is,” he said. “I have 12 horses coming in this year, so if I can win between 10 and 12, that would be sweet. “Really, you have eight or ninth months to try and win one race with every horse. It shouldn’t be that difficult, but it is.
“I told myself I would give myself three years in racing and then I would re-evaluate. So, this is actually my last year to re-evaluate and to see if I continue going forward. I wanted to give it a fair shot, but I knew I wasn’t going to hit the ground running. So at the end of the year we did fairly well and I’m back, but very optimistic.”
Di Paola notes there is one factor, as intangible as it may seem, that plays a role in his line of work.
“It pretty much boils down to hope,” he offered. “Anybody can breed a Queen’s Plate winner. It doesn’t necessarily mean that (trainer) Mark Casse is going to win every year or (trainer) Josie Carroll is going to win every year. It can come from anywhere.”
Hard work in one corner, hope in the other, there’s only one other piece of advice Di Paola offers for those looking to follow in his footsteps.
“You also need to establish a great team,” he said. “You need quality people behind you. When I actually went down, the Woodbine community was very concerned. My phone had a 100-something missed calls and messages. But my team, Tyler, Joey and Junior, were there and they brought me back up, and that’s part of the reason I’m coming back. The team, they are good people.”

Photo: D's Ben and Tyler Gaskin.

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