As the sun set against the majestic backdrop of Santa Anita Park Nov. 2, it framed a day that encapsulated all the raw emotions—the joy and severe heartbreak—that has propelled Thoroughbred racing in America for more than a century.

There was the unbridled joy of the connections of Vino Rosso , who stormed to victory over favored McKinzie in the $6 million Longines Breeders’ Cup Classic (G1) for owners Mike Repole of Repole Stable and Vinnie Viola of St. Elias Stable and seven-time Eclipse Award winner Todd Pletcher—a trainer whose résumé had been missing a Classic win at the Breeders’ Cup.

Repole, 50, remains as brash as he was as a teen growing up in Queens, N.Y., dreaming of making a fortune so he could buy racehorses, with the hope of winning races like the Classic. Earlier in life, he became a billionaire through his business dealings, and Saturday he won a race he watched and dreamed about as a youth.

“This is unbelievable. Indescribable,” Repole said. “We’ve won so many graded stakes, but this one feels different. Winning with Uncle Mo  (in the 2010 Grey Goose Breeders’ Cup Juvenile, G1) was amazing, and I knew it would take a special race to get a feeling even bigger than that. This is the one. This is the pinnacle.”

Viola—more reserved than Repole, as you would expect from someone with United States Military Academy training—lists owning the NHL’s Florida Panthers on his business portfolio, but after winning the Classic and adding it to a victory in the 2017 Kentucky Derby Presented by Yum! Brands (G1) by the Pletcher-trained Always Dreaming , he called himself “the luckiest person in the world.”

For Pletcher, the sport’s all-time earnings leader, there was special satisfaction in posting his first win in the Breeders’ Cup’s richest race with Repole.

“Mike and I have been together for a long time, and this was one that we hadn’t won,” Pletcher said. “It’s special.”

And yet, on racing’s biggest stage, there was also gloom stemming from the kind of tragedy that breaks the heart of everyone involved in the sport, producing a deep and profound sorrow. 

Mongolian Stable’s Mongolian Groom, who won the Sept. 28 Awesome Again Stakes (G1) at Santa Anita, sustained a fracture to his left hind limb in the stretch that resulted in the 4-year-old Hightail  gelding later being euthanized.

“The death of Mongolian Groom is a loss to the entire horse racing community,” Breeders’ Cup said in a statement. “Our equine and human athletes’ safety is the Breeders’ Cup’s top priority. We have worked closely with Santa Anita leading up to the World Championships to promote enhanced equine safety. Santa Anita has implemented numerous industry-leading reforms to enhance the existing health and safety measures with the intent of providing a safe racing environment. In addition, Breeders’ Cup always observes the most thorough up-to-date medication practices and restrictions, testing protocols, equine security and surveillance program, veterinary exams, injury management protocols, and racing surface testing. These measures are in place to ensure our athletes are racing under the safest and most transparent conditions possible.”

Breeders’ Cup also announced respected veterinarian Dr. Larry Bramlage would conduct an independent evaluation of the gelding, and the results will be published. 

“We are committed to working with our partners in the industry to continue to advance safety reforms, with the well-being of our athletes in mind,” the statement said.

Before hearing about Mongolian Groom’s death, Pletcher did his best to explain how safety and caring for horses was paramount to everyone involved in the two days of racing that did not have an incident until the final race.

“It’s something we were all very concerned about coming in and anxious not only for running in huge races like these but also hoping everything would go smoothly. I think everyone took every possible precautionary measure,” he said.

Mongolian Groom became the 37th equine fatality at Santa Anita since December, a total that has placed the industry under intense scrutiny.

The death of Mongolian Groom cast a pall on what had been an exciting day of racing in front of a crowd of 67,811. 

Vino Rosso closed the book on the 36th edition of the Breeders’ Cup with a victory that was set in motion in May when his connections sent him to the Gold Cup at Santa Anita (G1), a dress rehearsal of sorts for the Classic at the same 1 1/4-mile distance.

When Vino Rosso notched a three-quarter-length victory that day, Pletcher had a blueprint for how to return in the fall and head home with a second—and richer—grade 1 win.

“I think as much as getting out over the track, it gave us confidence that the horse handled the track. We knew he would love a mile and a quarter,” Pletcher said. “But also, for me, you’re always trying to figure out, like, when’s the best time to ship: Do we want to ship five days out? Do we want to work over the track? But we had a blueprint in place that worked. So we tried to follow that pattern exactly, and we did. And, like I said, the horse, he was just crawling out of his skin, literally, and the way he was breezing, coming into it, you’re just so anxious for the moment to get here.”

Winner of the Wood Memorial Stakes Presented by NYRA Bets (G2) last year at 3, Vino Rosso followed his victory in the Gold Cup with a third-place finish in the Whitney Stakes (G1) at Saratoga Race Course on a racetrack he does not relish. 

The son of Curlin  was then entered in the Jockey Club Gold Cup Stakes (G1) at Belmont Park, where he prevailed by a nose over Code of Honor but was disqualified and placed second behind the Runhappy Travers Stakes (G1) winner for bumping in the stretch. Code of Honor finished seventh in the Classic. 

In the weeks following the Sept. 28 race, Vino Rosso continued to thrive heading into his final race before heading to Spendthrift Farm for a life at stud, and Pletcher became unusually optimistic.

“Todd is a very efficient communicator,” Viola said, “so you have to pick up on his signals. So when you get texts that are un-Todd-like, I turned to (my wife) Teresa and said, ‘I think this horse is really going to run a special race.’”

That special race materialized on the final turn as Vino Rosso and jockey Irad Ortiz Jr. moved up quickly from fourth and collared the dueling leaders in front of him. McKinzie tried to hold him off, but in the final furlong Vino Rosso took charge and drew off to win by 4 1/4 lengths in 2:02.80 for the 10 furlongs. The winner paid $11.20 on a $2 ticket.

“He ran great,” said Joel Rosario, who rode McKinzie. “On a couple of occasions, we got slightly stopped in the run and had to take back. At the top of the stretch, I thought we might have had enough to get home, but he just got tired toward the end. I let him run a little bit on the backside just to get my spot. That might have cost him a little bit. He ran his heart out, so we can’t be too disappointed. We were just beaten by the best horse on the day.”

McKinzie—the 5-2 favorite trained by Bob Baffert and owned by Mike Pegram, Karl Watson, and Paul Weitman—had 4 1/4 lengths on Hronis Racing’s Higher Power, who was third for trainer John Sadler. Both McKinzie and Higher Power finished behind Mongolian Groom in the Awesome Again.

Ortiz had back-to-back wins in the day’s richest races. He also took the Longines Breeders’ Cup Turf (G1T) with Bricks and Mortar.

“I’m blessed. Thank God for everything, keeping me in one piece, keeping me healthy. I really work to do what I love to do, riding horses. And thanks to my agent, Steve Rushing, for doing a great job finding me those kind of horses to ride,” Ortiz said.

Vino Rosso was bred in Kentucky by John Gunther, who also bred last year’s Triple Crown winner, Justify , a point not lost on Repole.

“John and Tanya Gunther, obviously, are great breeders. I don’t know if you guys know this, but Stay Thirsty  (Repole’s 2011 Travers winner) was bred by the Gunthers, and so I’ve had some success when these horses run in my silks. But they have been great breeders. And just think, Justify and Vino Rosso, in the same crop, in the same pen. It’s pretty special, a Triple Crown winner and a Classic winner, side by side for the first couple years of their life. It’s pretty special.”

The win was the sixth in 15 starts for Vino Rosso and increased his earnings to $4,803,125. He is set to stand the 2020 season at B. Wayne Hughes’ Spendthrift Farm.

“When he was coming up to the top of the stretch, I planned a mission of sending Todd and Mike to Mr. Hughes’s house in Kentucky. I think we got to get a letter-writing campaign, because this horse might do some stuff really, really special in the future,” Viola joked. “But, no, he’s Mr. Hughes’s horse now, so we’re very lucky that he agreed to stand him and he had confidence in this horse as a stallion, and we’re very blessed to be partners with him on it.”

Vino Rosso was purchased by Repole and Viola for $410,000 from the Glennwood Farm consignment at the 2016 Keeneland September Yearling Sale. Jimmy Crupi, a longtime adviser for Repole and Pletcher, advised them to buy the colt and then raised him on his Florida farm.

Crupi died in May at 79, and Viola spoke passionately about the important role Crupi played in Saturday’s victory.

“Jimmy Crupi really understood this horse. He was like a blue-chip high school prospect that had a really great college career that had to learn how to be a great pro,” Viola said. “I think Todd and Mike would agree the person who oversees the breaking and initial training of a horse is probably as critical as any part of the team. And Jimmy, wherever you are, I know you’re in heaven, we love you very much and this one really, really was because of and for you.”

Sadly, Crupi’s passing was not the only loss mourned at a Breeders’ Cup filled with both tears of joy and grief.