Ask Hall of Fame jockey Pat Day about the pivotal victories of his career, and the conversation reaches beyond the finish line. Recently, he looked back on his four Breeders’ Cup Classic victories and the moments that shaped his life. He considers himself blessed. Over 33 years, he recorded 8,803 wins from 40,305 starters that amassed more than $297.9 million in career purse earnings, according to Equibase statistics. His victories include nine in Triple Crown races. He rode in 117 Breeders’ Cup races, including the first 21 Breeders’ Cup Classics.

Day, age 4, riding bareback on a family pony. (Courtesy of Pat Day)

Long before those victories, there was “Blackie.” Day’s earliest memory of a horse reaches back to his grandfather’s pony rides at South Dakota fairs, where he thinks he may first have sat on a horse. His father, Mickey, later bought two ponies: Blackie, a Welsh pony; and “Miss Claremont,” a Shetland pony. Back home in Colorado, Mickey saddled the barely broken Blackie and put Pat aboard. “I didn’t know anything except what I’d seen on TV about cowboys who are always kicking and yelling and off they go. I yelled ‘Yee-haw’ and Blackie took off running. The faster he went, the louder I screamed. The louder I screamed, the faster he went.” When Blackie finally stopped, Day jumped into his father’s arms. Mickey set him down, wiped his eyes and assured him he was OK. Then he insisted Pat get back on Blackie and led him back to the house — a lesson Day would never forget.

“That could have been a pivotal moment in my life, because I didn’t want to get back on him. I was horrified. But had my father given in to my desire not to get back on him and allowed that seed of fear to take foot, it could have definitely altered the trajectory of my life.” Mickey also insisted that Pat and his siblings ride bareback for a long time. As Day remembers his father saying, “I want you to learn how to ride the horse, not the saddle.” Day later helped Mickey break the neighbors’ horses. “I acquired a lot of horsemanship from my father. It was a great childhood.”

The horsemanship came early; the idea of becoming a jockey did not. Day tried bull riding at rodeos and worked on an oil rig, at a gas station, at a ski resort, and as a plumber’s helper before finding his way to the racetrack. There, his natural talent brought rapid success. “I had no intention of being a jockey, but I believe that God had his hand on me and directed me in spite of myself.” Success also unsettled him. “I was always small and had an inferiority complex. Now I’m having this tremendous success, and I go to the other end of the spectrum. I was partying like a wild man.” In January 1984, his life changed course. Day describes a spiritual revelation in a Miami hotel room that freed him from the bondage of drugs and alcohol. 

The same year brought a professional turning point. Hollywood Park hosted the inaugural Breeders’ Cup, and a series of serendipitous circumstances put Day aboard Wild Again (Icecapade – Bushel-n-Peck, by Khaled) in the Classic. Wild Again, trained by Vincent Timphony and owned by Black Chip Stable, carried an extraordinary investment into the race: his owners had paid a $360,000 supplemental fee to make him eligible.

Wild Again, inside under Day, would not be denied. (Breeders' Cup photo)

The eight-horse field included Slew o’ Gold, Gate Dancer, and Track Barron. Day remembers Wild Again breaking sharply and settling into stride. “We broke and ran away from the gate. He’s relaxed and in hand.” When Slew o’ Gold challenged outside him, Wild Again would not yield. “He refused to get beaten when Slew o’ Gold ran up on the outside of him. He just dug down. I’ve never been on a horse before or since that tried any harder than he did in the last quarter of a mile. He refused to let them horses by him, almost as if he knew that his people had put up $360,000 to give him this opportunity and he wasn’t going to let them down. I could hear him grunting. I could feel him straining. He was giving me 110%, and I was content to just hold him together and help him and try to keep him straight. What a race!”

After a lengthy inquiry and the disqualification of Gate Dancer, Day and Wild Again were declared winners of the $3 million inaugural Breeders’ Cup Classic. Day remounted Wild Again for the winner’s circle. “The Lord was the furthest thing from my mind. I was pretty keen on old Pat Day. You’re human. Breeders’ Cup! A $3 million race! I’m pretty puffed up and the crowd is going wild.”

He removed his helmet, intending to wave and receive the cheers. Instead, in a moment of revelation, he raised it in humble thanks. Photographers captured the gesture, which became an iconic moment in horse racing history.

Day believes the Classic victory contributed significantly to his selection for the 1984 Eclipse Award as outstanding jockey. He also won the award in 1986, 1987, and 1991.

Day, in 1969, with a horse he helped his father break. (Courtesy of Pat Day)

Between 1985 and 1990, Day finished second in three Classics. In 1986, he rode the Classic favorite, Turkoman (Alydar – Taba, by Table Play), who he remembers had a distinct dislike for Santa Anita Park. They finished behind Skywalker (Relaunch – Bold Captive by Boldnesian).

In 1988, Churchill hosted the Classic before the track had evening lights. Day remembers an overcast, gloomy sky that was nearly dark by race time. Riding Seeking the Gold (Mr. Prospector – Con Game, by Buckpasser), he finished behind Alysheba. “He ran a big race but by the time the race ran, it was past dusk. He got a good trip and fired hard off the turn and just came up second best. Alysheba obviously was a very good horse!”

In 1989, Day guided Easy Goer (Alydar – Relaxing, by Buckpasser) to second behind Sunday Silence, who, Day recalls, ran around the turns faster than he did down the straightaways. “Easy Goer changed leads and just spit the bit out. Now I’m fishing. I’m shaking him up, I’m shaking the reins at him, I’m screaming at him; I flip my stick up and I get no response. He finally changed leads late. We came up with a diminishing neck short. Be that as it may, we wound up second best.  Sunday Silence changed leads and ran away. He was a good horse.”

In 1990, Day won the Florida Derby aboard Unbridled (Fappiano – Gana Facil, by Le Fabuleux). That fall, the Breeders’ Cup at Belmont was marred by tragedy. Chris Antley’s mount, Mr. Nickerson, suffered an apparent heart attack, and Antley fractured his collarbone. During the Distaff, Go for Wand fractured her ankle, collapsed, and had to be euthanized. A beautiful, sunny fall day in New York had taken a devastating turn. “I see it in my mind. It was like it was slow motion as I’m watching it. It turned me inside out. I wanted to go home.” After talking with Angel Cordero, Day asked Tony, the clerk of scales, to gather people together. The chaplain, jockeys, valets, and media met in the recreation room to pray — a gathering Day felt turned the tide on a difficult day.

With that gathering behind him, Day went to the Classic aboard Unbridled, the 1990 Kentucky Derby winner, who broke from post position 14. He remembers a flawless trip on the Carl Nafzger-trained 3-year-old. “Carl had done a marvelous job getting him up to the race, and he stepped up to the plate and just ran lights out.” Nafzger put it simply: “It was a classic ride on a classic horse.” Unbridled won the Classic and the Eclipse Award as the champion 3-year-old male of 1990.

Day wins 1998 Classic aboard Awesome Again. (BloodHorse/Skip Dickstein)

Eight years separated Unbridled’s victory from Day’s next Classic win. When that victory came, it would be against a field whose depths made it especially memorable. The 10-horse field included Silver Charm, Swain, Skip Away, Touch Gold, and Victory Gallop. Day was undaunted. He had already won four races aboard Awesome Again (Deputy Minister – Primal Force, by Blushing Groom): the Grade 2 Stephen Foster Handicap, Grade 1 Whitney Handicap, Grade 2 Saratoga Breeders’ Cup Handicap, and Grade 3 Hawthorne Gold Cup Handicap.

Day recalls watching the race unfold from behind the field. “We were at the back of the pack. When we came off the turn, it was like the parting of the Red Sea. Silver Charm and Swain (Ire) drifted way out past the middle of the racetrack. Awesome Again dropped down, fired and came home running and got the money. It was a great race!”

Day’s fourth Classic victory came in 1999 aboard Cat Thief (Storm Cat – Train Robbery, by Alydar), trained by D. Wayne Lukas. Earlier that year, Cat Thief had won the Swaps Stakes at Hollywood Park. Problems with his feet prompted his team to try glue-on shoes for the first time, and in the Classic, he responded willingly to Day with a determined winning effort. Lukas called Day an intuitive rider and praised him in the winner’s circle: “We’ve been on a roll all summer and he came through when it counted.” Their relationship had survived the ups and downs of a tough business. “We had a great relationship,” Day says, his voice softening. “He hired me and fired me several times but that’s part of the business. I never took it personally.” Their bond reached beyond racing: Day baptized Lukas when the trainer decided to spend his final days at home before his passing June 28, 2025.

Lukas congratulates Day aboard 1999 Classic winner Cat Thief. (BloodHorse/Rick Samuels)

Looking back, Day sees the inaugural Classic as the victory that changed the scale of his career. “The Breeders’ Cup was certainly good to us. I can’t even put into words what the Breeders’ Cup has meant to my career. I believe that the Classic victories catapulted my career to the next level. I started receiving opportunities to participate in all the major races. I was getting choice horses. It really catapulted my career to the stratosphere.” (Day won 12 Breeders’ Cup races with 40 top-three finishes from his 117 starters.) 

Today, he is thrilled by the event’s growth and the talent it attracts. “It has grown by leaps and bounds. It’s an extravaganza with the best of the best in all categories: dirt, grass, short, long. An exciting two days of racing!”

Thirty-three years, 8,803 victories, numerous awards and accolades and a place in the Hall of Fame tell the story of an extraordinary career. But the image of Day raising his helmet after Wild Again’s Classic victory offers something the record books cannot: a glimpse of what those achievements mean to him. From the boy who reluctantly climbed back aboard Blackie to the jockey who won four Breeders’ Cup Classics, his journey brought him farther than he ever imagined. As each Breeders’ Cup brings forward great racing, Day can look back on the victories that shaped his career with the gratitude captured in that raised helmet. He considers himself blessed.