“Waiting eighteen years to win a stakes race ‒ it’s just a crazy feeling. When I look back at the video, I look like I can’t stop smiling. It was just the most amazing feeling, and it stayed with me for days after. I couldn’t believe it had finally happened to us.”

There is still a triumphant tone in Angelo LaMantia’s voice as he talks about Mason’s Gamble and his victory in the Ontario Jockey Club Stakes last month. LaMantia and Anthony DiPierdomenico (ATA Stables, Inc.) own the four-year-old stakes-winning colt and have been involved in the industry for nearly two decades.

Their initial introduction into the game was due in large part to another good friend, Colleen Dalos, who has known Angelo and Anthony since they graduated from university. Colleen is the general manager of operations and marketing for Tall Oaks Farm for the operation’s breeding and racing elements. Colleen’s father, Ivan, is Tall Oaks’ founder and has been a prominent force in Ontario’s racing and breeding game for over 40 years. A breeder of champions, Dalos’ ‘breed to race’ program is focused on racing homebreds from Tall Oaks.

Back in 1994, when Colleen decided to buy her first horse at the Canadian Breeders yearling sale, both Angelo and Anthony were part of the process. She purchased Hip 126, a Secret Claim filly out of Dawn’s Deputy, and named her Gambling Girl.

Colleen Dalos calls sending Gambling Girl to the Tall Oaks broodmare band “one of the greatest ideas we’ve ever had.”

“Angelo, Anthony, and all my friends were extremely excited and involved right from the beginning, said Colleen. “Unfortunately, she wasn’t ready to race when she was two, so Gambling Girl debuted in 1996. Angelo and Anthony and all the gang were there for the first race and the first win picture ‒ it was five-and-a-half furlongs, 10-horse field, a maiden allowance. We all still remember it well. She went off at high odds and won by 8-10 lengths. It’s the most thrilling day that we can all remember. It’s so fun to look back at that win picture because it would be 26 years ago now.”

Gambling Girl had a successful career with seven wins from 21 starts, including a victory in the ’96 La Prevoyante stakes. However, near the end of the following summer, a chip in her knee would bring the stakes filly’s racing career to an end. Colleen gave the mare to her father to be part of the Tall Oaks broodmare band. It’s a decision she is very pleased about.

“Probably one of the greatest ideas we’ve ever had, because we’ve had Gamble’s Ghost, Gamble’s Exchange, Forest Gamble and a whole slew of great horses come out of her.”

Gamble’s Ghost, a daughter of Ghostzapper out of Gambling Girl, won multiple stakes at Woodbine. Her resumé includes a handful of Grade 3 stakes wins in the Mazarine (2015), Selene (2016), Maple Leaf (2017), Trillium (2018), and the Ontario Matron (2018).

Over a decade ago, Gambling Girl was bred to Exchange Rate and produced a dark bay colt named Gamble’s Exchange. The bloodline on the dam and sire’s side indicated a bright racing future for Gamble’s Exchange. However, fate would bring him into a stud career earlier than anticipated.

“Gamble’s Exchange never raced because he had an early injury, but my dad loved Exchange Rate, and he really believed he [Gamble’s Exchange] was going to be great horse and he wanted to make him a stallion. Everyone laughed at him, everyone told him he was crazy, nobody would stand the horse, so my dad just decided to keep him for ourselves,” said Colleen.

Gamble’s Exchange. (courtesy Colleen Dalos)

Gamble’s Exchange is one of four stallions that represent Tall Oaks’ breeding operation. He stands alongside another Tall Oaks stallion, Amis Gizmo, at T.C. Westmeath Farm in Mulmur, Ontario. Tall Oaks also stands Ami’s Flatter at Ocala Stud Farm and Ami’s Holiday at Colebrook Farms Stallion station.

The history of one horse lends itself to the story of another. In this case, Gambling Girl produced Gamble’s Exchange, who is the sire of Mason’s Gamble (out of Dynaco). Mason’s Gamble is named after Anthony’s son, Mason. Nearly all of Anthony and Angelo’s horses have been named after their kids – Anthony’s Tessa, David and Mason, and Angelo’s Isabella, Jessica and Anthony. The only exception was their first horse, Urge to Go, who was purchased in 2004 and was fourth in the 2004 Coronation Futurity, trained by Kevin Attard.

In 2005, they purchased a daughter of Bold Executive at the CTHS yearling sale. She was named Bold Isabella, after Angelo’s first daughter, Isabella.

“She ran her first race, broke her maiden, and was never losing. She got an injury and had surgery and was not the same. We decided, ‘Hey, why don’t we breed her,’” said LaMantia.

Bold Isabella would go on to produce Jessica’s Peak, David’s Brew, and Where’s Anthony. Anthony and Angelo also raced and owned a filly called Victory for Tessa back in the mid-2000s.

Each of those horses got to the winner’s circle, but none of them were able to clinch a stakes victory during their careers. Where’s Anthony came the closest with a fourth-place finish in the 2018 Bold Ruckus Stakes.

So how did Mason’s Gamble enter the picture?

Angelo explained candidly, “What ended up happening is we weren’t sure we wanted to carry on [racing] anymore. But Anthony was adamant: ‘Hey, we need to have one named after my son Mason.’ I was the one who wanted to walk away or have a long break or whatever, but Anthony can convince me to do anything!”

The next step was to find a prospective racehorse. This task was not too difficult for the two friends since they knew a couple of people with a good eye for a horse willing to lend a hand in the purchasing process.

“I really wanted to make sure we gave them a good one, or the best that you can. I looked through the horses we had and my father and I selected Mason’s Gamble. Anthony and Angelo came up to Paul Buttigieg’s where the horse was; we showed them the horse and talked to them about it and did a private sale when he was a yearling, right after the CTHS sale,” said Colleen.

Over the years, Anthony and Angelo’s horses have been trained by various conditioners at Woodbine. The training of Mason’s Gamble is overseen by Hall of Famer, Josie Carroll.

“We all agreed as a team that they would follow the Tall Oaks program, and they would have Josie Carroll train the horse and follow the same protocols as we do because we very much cared about launching the stallion.”

The colt made his racing debut last year and won four of his starts and also finished second in the Elgin Stakes. This year, on June 19th, he won the Ontario Jockey Club Stakes, posting a 103 Beyer figure. In 2021/22, Mason’s Gamble is Gamble’s Exchange’s leading progeny (his all-time leading earner is Dixie’s Gamble).

Watch the Ontario Jockey Club Stakes and post-race interview here:



The owners are more than content with the colt’s performance so far and Colleen is very happy for her friends. She is also keenly aware that we need more people like Angelo and Anthony and their kids in the game.

“Like any industry, we need to generate new interest and new owners, especially the younger generation. Besides the fact that we are all great friends and there is so much camaraderie, we are all having a great time; what I also love is that all the children are having a great time. So now we get the next generation pumped and wanting to come out to the racetrack, and they are telling their friends. So this is how I think we are going to get new people and grow the next generation.”

Angelo also acknowledges that it’s essential to get more people involved in racing. “I truly believe that the younger generation needs to get in it and keep on promoting it. I’ve had a lot of my children’s friends come out to the races and love being out there and just enjoying everything about it. I know it can get expensive, but that’s why you have groups with 10 or 15 people and they purchase a thoroughbred or a couple thoroughbreds, so the costs are broken down.

“I think it’s just the love of being around horses, too. My daughter Jessica just loves coming to the track all the time, and likes going to the barn in the winter where we keep Mason and feeding him carrots. I really hope more people get involved in Ontario and keep racing alive.”

Anthony also understands the ebbs and flows of the industry and knows that while not every race will yield a big win, you must still ride the wave with a particular attitude. “The key thing to all this is being patient and making sure you are having fun along the way. If you are not having fun, then it may not be for you.”

Mason’s Gamble may be one of the biggest winners for his sire, but as Colleen notes, there are more horses to come. “I have a fantastic Gamble’s Exchange out of Lonhro’s Collection, a very nice individual. We actually have three nice horses coming to the CTHS sale,” said Colleen. The other two yearlings are a Tapiture colt (out of Archerette) and an Ami’s Holiday filly (out of Henry’s Collection).

This year’s CTHS Yearling Sale will be held on August 31st at Woodbine Sales Pavilion – the same sale where Gambling Girl made her way into Colleen’s hands 28 years ago.

In the meantime, Mason’s Gamble will stand in the limelight for his sire and his owners on a journey that is all about having a dream and being willing to gamble on it.