You could always bet on Pat Day to win. Retirement hasn’t changed that.

Jockey Pat Day, retired since 2005, shows the George Woolf Memorial Award he won in 1985. His peers voted him winner of the award which generally is given for sportsmanship and riding success. Day won the Breeders' Cup Classic four times.
Jockey Pat Day, retired since 2005, shows the George Woolf Memorial Award he won in 1985. His peers voted him winner of the award which generally is given for sportsmanship and riding success. Day won the Breeders' Cup Classic four times.

Time was when the turning of autumn leaves at Keeneland brought Hall of Fame jockey Pat Day to anticipate the Breeders’ Cup.

Fall was Day’s time of year. Winner of four Breeders’ Cup Classics and an additional eight Breeders’ Cup races on the sport’s annual championship weekend, Day owned the event. Keeneland was the run-up. Fanine Triple Cerons counted on him stoking his competitive fires in Lexington to pay off (and sometimes at big payoffs) on Thoroughbred racing’s big day.

Twelve years after his retirement in 2005, Day, 64, does not miss race-riding. He’ll attend the Breeders’ Cup Nov. 3-4 at Del Mar near San Diego without any sentimental urge to put on those white pants one more time. The pants would no longer fit. Day has gained 15 pounds from his 100-pound riding weight. Relaxed and happy, he speaks enthusiastically about retirement life.

The story that unfolds during an interview at Starbucks is far from racing, far from any fan’s memories of Day in that inaugural $3 million Breeders’ Cup Classic of 1984 at Hollywood Park. No one could be sure the event would grow into the global success it has attained. Topping off the event was Day winning on Wild Again by a head despite Slew o’ Gold bumping him repeatedly through the stretch. Wild Again paid a whopping $64.60 but that was only part of the story. In that inaugural event stewards made a controversial decision, disqualifying second-placed Gate Dancer to third because he had begun a chain reaction, pushing Slew o’ Gold into Wild Again. The incident was difficult for fans and Slew o’ Gold’s owners to discern from race replays. They all thought Wild Again the culprit.

“That race catapulted my career,” Day said. To win that race, then the richest in the United States, in front of the country’s elite horsemen and before a national television audience rivaling Kentucky Derby ratings launched Day from regionally successful rider on the Kentucky, Arkansas and Illinois circuit into the company of go-to jockeys for major stakes races.

More was happening to Day than many were completely aware of at that Breeders’ Cup. Earlier that year — amid a troubled time centered on substance abuse — he had experienced an overwhelming conversion to Jesus Christ. As Day’s profile increased in the top jockey ranks, he spoke more and more openly about that experience. He briefly considered retiring in 1984 to attend seminary. He did not, and for the remainder of his career he used his platform at racing’s elite level to deliver a Christian message. When it came time to retire, he relied on guidance he says came directly from his savior.

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Pat Day is president of the Kentucky Race Track Chaplaincy Council. Day said upon retiring from riding that “almost immediately there was a renewed enthusiasm, not to ride and win races but to win souls for the kingdom of God.” Beth A. Keiser AP

In 2005, Day was making a comeback from minor hip surgery in March. Later that spring he won the Fleur de Lis Stakes at Churchill Downs. He was approaching the finish, expecting the adrenaline rush and euphoria to hit as it always did when he won — yet he felt nothing.

“It was the first, last and only race I’ve ridden in where I didn’t have any emotion at all,” he said. He continued riding. In mid-July after riding in the Delaware Park Handicap he flew home with a friend and told him he felt unsettled. Day said he needed to get away and spend time praying. He needed answers: Why was he not enjoying winning? Was retirement time sneaking up on him?

Pat Day is the all-time winningest jockey at Churchill Downs (2,482 first-place finishes) and at Keeneland (918).

Day’s friend owned a cabin near Wilmore, on the Kentucky River, and gave him the keys. He told Day to stay alone there as long as he wanted. In early August, Day went to the cabin, cried a lot and said he begged Christ to rekindle the flame and keep him in racing because, “I loved riding.” But not even Day could deny that his heart no longer was in it, that the competitive fires had died.

Day said he presented his arguments to Christ. The jockey was only 30 winners behind Bill Shoemaker on the all-time wins list. Day thought he wouldn’t need much more time to surpass Shoemaker. But on a higher level, that argument, according to Day, carried no weight.

More, his mounts had earned $297,914,839 and, as Day told Christ, he was getting nice horses to ride and expected to pass the $300 million mark by year’s end. Like the leading winners list, that failed to carry weight with his higher power.

“Finally, I just broke down and cried and said, ‘Father, I just want to do what you want me to do,’” Day recalled. “At which point he picked me up and held me, spiritually speaking, and it was the most secure and comforting feeling,” Day said. At the end of three days he knew the time had come to retire. “I knew that it was the end of my racing career. Almost immediately there was a renewed enthusiasm, not to ride and win races but to win souls for the kingdom of God.”

Pat Day won 12 Breeders’ Cup races and nine Triple Crown races, including the 1992 Kentucky Derby.

And that is what Day is doing in retirement. Though he told his story in Starbucks, nestled in among the latte crowd, he is anything but idle. He speaks to prayer breakfasts. He attends weekly chaplain’s services at Churchill Downs. That morning he met at 6 a.m., as he does each Friday, with a surgeon to uplift and encourage each other with scripture.

On Tuesday mornings he meets first with a group of four that studies scripture, then meets with a pastor who is mentoring him in the same. On Wednesday afternoons Day meets an elderly acquaintance for scripture study at Starbucks. On Saturday mornings, he attends men’s Bible study at Northeast Christian Church in Middletown. He also is president of the Kentucky Race Track Chaplaincy Council, and is introducing a new chaplain and assistant to race track life at Churchill Downs. A number of persons ask him on Facebook or with texts for prayer and support.

Pat Day won the 2003 Travers Stakes aboard Ten Most Wanted. He retired two years later. Horsephotos/NTRA

“I’m easily recognized, so I have the opportunity through the day with people I meet to share with them and encourage them,” he said.

“God’s got my day lined out, so I try to be open. I get up early, spend time in prayer and reading and studying scripture, and spend time with (wife) Sheila. It’s not like I have a set schedule.”

On the home front, Sheila Day is preparing for a show where she will display the jewelry she designs and makes. The Days had a recent hectic weekend, when their daughter and only child, Irene, married on a farm in Shelbyville.

In the lower level of their custom-built home in Forest Hills, the Days display the spoils of Pat’s riding career in trophy cases that run along two walls from floor to ceiling. Occupying its own case at the center of the room is the silk replica of Lil E. Tee’s Kentucky Derby roses, won by Day in 1992.

Like Wild Again, Lil E. Tee was a long shot to win, paying $35.60. But the real long shot was Day, finding Christ and turning around his life, and now bringing Christ’s message to everyone he meets.

Winningest jockeys

Jockey: Wins

Russell Baze: 12,842

Laffit Pincay: 9,530

Bill Shoemaker: 8,833

Pat Day: 8,803