Memories of a Master

The Determined Life of Dickie Small

Maryland native Richard “Dickie” Small remained sharp as ever until his death on April 4, 2014 – with an uncanny eye for talented runners and a storyteller’s gift for weaving together the threads of his fantastic past.

Jim McCue

May 12, 2014

Morning after morning this past winter, Richard “Dickie” Small rolled his truck onto the grandstand apron at Laurel Park and sat between the eighth and sixteenth poles, running the heat inside the cab to keep from catching cold.

Two months before he passed away, trainer Dickie Small relived the highlights of his colorful career Jim McCue

He watched his teams of horses gallop by, sent out by young assistant Dylan Smith. His once burly athlete’s body had wasted to unsteady bones under loose-fitting clothes, his thick hair a startling steel gray under a favorite beat-up newsboy cap. A cane lay propped against the passenger seat. He bore the haunted look of a man ravaged by late-stage cancer.

By the time doctors discovered the malignancy on Thanksgiving two years ago, the disease had spread throughout his body.

“I remember reading Walden,” Small said one January morning at Laurel Park, pushing his voice above a raspy whisper. “I’ll never forget reading it when I was a little kid. It said, ‘The mass of men lead lives of quiet desperation.’ I’m just a little kid, and I said, ‘Not f-ing me; I’m going to do whatever I want.’ ”

Once a trainer who preferred to get down in a stall and do the dirty work himself rather than have someone else do it wrong, in his final days 68-year-old Small had been reduced to fighting merely to remain present in what had become a shadow of his former life. It took something as relentlessly virulent as cancer to cut down a man who lived with such great gusto.

Small’s assistants speak of him with great respect

From parachuting clueless into top-secret missions in Vietnam to training the brilliant but ill-fated Caesar’s Wish and the quirky handicap star Broad Brush, to winning the Breeders’ Cup Classic (gr. I) with Concern, Small lived life on his own terms — and became one of the most accomplished horsemen in Maryland.

“The thing about getting sick is, I had a really full life,” Small said three months before he died. “I never missed a beat. I never missed one thing my whole life, and all of the sudden, ‘Oh, sh-t, I’m sick now.’

“It wasn’t like I was waiting for something to happen. I made things happen, you know?”

Making of a Master

Click on each photo below to learn more about Dickie Small’s life

Early Years

Young Dickie Small (2nd from left), flanked by brother Doug Small Jr. and father Doug Small Sr. after the 1955 Laurel Spring Turf Handicap Jerry Frutkoff


U.S. Army Bell UH-1D helicopters airlift members of the 2nd Battalion, 14th Infantry Regiment in South Vietnam, 1966 Wikimedia Commons

Becoming a Trainer

Caesar’s Wish, led here by assistant Kathleen Dibben with Small in the background, was the trainer’s first brilliant runner Blood-Horse Library

Early Years

Dickie Small got into the University of Pennsylvania in 1963 because he played good football, lacrosse, and ice hockey. His father had also been a student there. Ivy League schools don’t offer scholarships, but Small enjoyed perks — free room, free meals.

Because of his athleticism he had pretty much sailed through Gilman, a high-end prep school in Baltimore that serves as a pipeline to prestigious universities around the country. What had worked for him at Gilman, however, didn’t fly at Penn.

“I just played sports,” Small said. “I had already had all the [academic] stuff at Gilman, and I thought, ‘This is easy.’ I got what we used to call ‘gentleman’s C’s.’ After two years they said, ‘Look, you’ve got to grow up and start paying attention.’ I didn’t actually get kicked out, but I got a non-optional year off.”

In the mid-1960s, with the United States drifting deeper into the Vietnam War, young men with a non-optional year off were 1-A, at the head of the draft line.

Former exercise rider Richard Beck says Dickie Small was a natural horseman

The day Small got booted out of Penn, he drove to the University of Delaware and applied to summer school. With no desire to move back in with his parents at the family horse farm, Strathmore Stud, he took a job working for the famed show-jumper and steeplechase trainer Betty Bosley Bird, his mother’s good friend, in Unionville, Pa.

Small worked on Bird’s farm during the day and went to school at night, renting a house with Billy Turner, who was working for future Hall of Fame steeplechase trainer Burley Cocks and later became famous for training Seattle Slew. In three years Small earned a Bachelor of Science degree in animal science and agricultural biochemistry. In the summer of 1968, he went to work with the gate crew at River Downs racetrack. When his draft letter came, he didn’t even open it.

“I enlisted,” Small said. “The first day I got to boot camp at Fort Dix, and they put me in charge of the platoon. Of course, I was older. Most of the people that got drafted weren’t even weaned then, you know? They didn’t even know how to do their laundry.

“They had an hour class on how to do right face. At the end of the hour, there would be a couple of them that couldn’t do it. The next hour is left face. I’m not making this up. There would still be a couple that couldn’t do it. It was pathetic.”

Small wasn’t afraid of the Army. In fact, it suited him just fine. He was dead fit from playing sports and growing up on the farm. He also had worked as a wrangler on a California ranch for three summers while in prep school.

“I’d already been away,” he said. “I was on my own for years. These other kids came right off the nipple.”

Small was a ravenous reader of history — fascinated by country, lives, and lineage. He pored over books, archives, magazines, and newspaper clippings — especially about Monkton, Md., the land of his family, a national historic district called My Lady’s Manor. Wherever he looked, both past and present, he found his predecessors enjoying success. Why shouldn’t he?

Blood-Horse Library
Louis Weintraub/NYRA
Blood-Horse Library
Top: Doug Small Sr. (left) accepts a trophy for the Constellation Handicap at Laurel Park; Left: Doug Small Jr. at Aqueduct in June 1965; Right: Small’s uncle, Sidney Watters Jr., at the races in 1972

Small’s father, Doug Small Sr., had ridden in the prestigious Maryland Hunt Cup timber race before becoming a winning flat trainer. An older brother, Doug Small Jr., was a national steeplechase riding sensation who won the American Grand National — now the Breeders’ Cup Grand National Steeplechase — four times. His mother Jane, as good with horses as any of the others, ran the family farm. Her brother, Sidney Watters Jr., excelled as a steeplechase rider and trainer, and on flat tracks developed champions Hoist the Flag and Slew o’ Gold on his way to the Hall of Fame.

Records show Small’s grandfather and great-uncle winning Maryland Hunt Cups at the dawn of the 20th century, and his mother’s kin traced to the first English settlers at Jamestown. The bloodlines burned hot through the generations, full of carousing and excitement. Around 1640, when the rich Cavaliers, loyalists to the Crown, started ruling the Virginia colony with a heavy hand, many of the original settlers migrated up to Maryland. Robert Hutchins — Jane Watters Small’s ancestor — was among them.

“They were land rich, but none of them had any money,” Small said. “They would hunt and fish, and that’s all they did. It’s not like they were big planters. They’d mess around with horses and cockfighting.”

Small remembered coon hunting by moonlight with fox hunters in Monkton as a young boy; his mother’s cousin, Russell Hutchins, riding along.

His parents had urged him to find his own path away from horses as a couple of his siblings had done. The tide was strong, but first he went full-bore in the military at a time when most kids in the country were trying to do just the opposite.


“A lot of people went into the National Guard — a real lot of people that had, you know, education breaks, and the family had some resources,” Small said. “But [the National Guard] was like seven years, and I said, ‘Forget that.’ Everybody else went to France or Canada, and I haven’t seen them since.”

After completing advanced individual training, Small seized the opportunity to go to Officer Candidate School at Fort Benning in Georgia.

“This is a whole different type of people — almost all of them had had education and were motivated and smart,” he said. “OCS is really, really hard. There is enormous pressure. They want to make sure you’re not going to crack. I mean serious mental pressure. So I was paying attention and wound up finishing first in my class.

“So instead of just getting assigned something, I get to pick. I don’t know anything about the Army. I don’t know what the infantry is. So I said, ‘I’ll take special forces.’ I know it’s a more elite thing; that’s basically all I know. But I know it’s a step up.”

It turned out he had stepped up — to the sky, to jump school. This certainly was not Thoreau’s life of quiet desperation.

“Jump school’s not that easy,” Small said, “but it was easy for me.”

Vietnamese paratroopers jump from U.S. Air Force Fairchild C-123B Provider transports in the initial air assault wave during "Operation Phi Hoa II" against the Viet Cong in the Tay Ninh Province of South Vietnam during March 1963. Wikimedia Commons

The first time Small and his class were taken to Fryar Field to parachute, the plane took them to 1,200 feet. The jumpmaster went over final instructions.

“Just when I went up to jump, the guy behind me threw up all over my bag,” Small said. “I’ll never forget it. I get to the door, and the guy puked all over my parachute.”

Small turned and hopped into the sky.

The Army accelerated his training. Soon, he was off to the Jungle Operations Training Center in Panama — jungle school.

Sitting in his truck at Laurel, telling the story, Small waved off questions about whether this assignment had been difficult.

“I had already been to special forces, so jungle school was like kindergarten,” he said.

Small made a buddy there, a guy who he said had finished first in his class at West Point.

“They take you out in the swamp,” Small said. “They tell you, ‘OK, we’re going to spend the night here,’ and the water’s up to your knees. So, there’s a way to do your hammock and poncho, and I could do it blindfolded. I helped him with all this stuff. Actually, it was kind of cool. They had this big mountain … and this real, real high waterfall, and we repelled down that. I’m fit, you know? Country boy. Everybody else has their tongues hanging out.”

It was time to go to South Vietnam. Small and his pal flew to Sausalito, Calif., to spend a few last nights partying with some girls he had met during his wrangling days. Once in Saigon, Small’s friend — an infantryman — was picked up within an hour of arrival. Small had to stay behind a few days before heading north to Nha Trang, headquarters for the Fifth Special Forces Group, on the south central coast.

In no time at all, word came back his friend had been killed. Small hadn’t even left Saigon.

Asked his friend’s name, Small said only, “I wanted to go down and look on the wall,” — the Vietnam Veterans Memorial in Washington — “but I never had enough balls to go down there.”

Nha Trang J Y White/Wikimedia Commons

Nha Trang is a land of stunning beachfront and now an international tourist destination. Small spent three or four months there, doing cushy duty, pushing paper around. He didn’t know what was coming but got a sobering sense one day when he went to a dispensary to pick up his medical records and saw a dead man on the ground by the door.

“So I walk in like it’s perfectly normal, and there’s flies flying around this guy,” Small recalled. “I said, ‘What happened to him?’ They said, ‘Oh, he got on his back.’ Well, I had no idea what that meant. I eventually found out.

“This is where I learned how to freefall. When you jump, you fall and face the earth, and you sort of arch your back and you stay facing the earth. You actually move your arms and you can sail around the sky. But … you can flip over, and when you flip over, of course, your parachute can’t open.”

The army began to take the Military Assistance Command, Vietnam — Studies and Observations Group out for freefalls. Each day the plane would fly a little higher. Small often jumped five or six times a day. Most of the jumps were from 15,000 feet, but sometimes the plane went up to 30,000.

“It was a kick,” Small said. “From that, it’s like a 30-second freefall.”

Small said his Uncle Sidney later told him that in Saratoga in the summer of 1970, people were making book on whether he’d come back alive. “Everybody was like, ‘What is Dickie doing?’ I didn’t know myself.”

Mister Diz wins the Philadelphia Turf Handicap at Atlantic City in New Jersey Aug. 22, 1970 Jim Raftery/Turfotos
Sidney Watters Jr. with Hoist the flag in 1971 Blood-Horse Library

At the time, Small’s father was riding high back home, training a terror named Mister Diz, who won or placed in 24 stakes races between 1968 and 1974. His uncle was doing even better: Hoist the Flag was running toward a juvenile championship in 1970 and early favoritism for the following year’s Kentucky Derby.

Small called home one day from a phone bank at the USO in Saigon and heard about those horses. His mother also told him his sister was getting married, so he skipped R&R in Thailand and flew to Maryland for the wedding.

Once he returned to Vietnam, Lt. Small and his team began their secret HALO — High Altitude Level Opening — missions in groups of four. He had no idea exactly what they were doing or where they were jumping. Orders were to land, check trails and supply routes, and conduct reconnaissance.

Brenda Jordan, one of Small’s longest-serving assistants, who called her years with him the best of her life, said he told her he cooked rice in the jungle by putting packets in his armpits. Asked how they eventually got out of the jungle at the end of a mission, Small said a helicopter would come in and lower a rope with latches. The men hooked themselves up and flew out dangling beneath the copter, pointing their guns in all directions.

Twenty-five years later Small was browsing the military section of a New Orleans bookstore and stumbled across a book called “Military Assistance Command, Vietnam.” The HALO reports of the U.S. military’s Studies and Observations Group had finally been declassified, and Small learned the true nature of his work. His secret parachute team was essentially a guinea pig outfit for a new kind of infiltration simply because none of his predecessors who used helicopters had returned alive.

“I read the book, and it scared the hell out of me,” he said.

When he finally returned home in August 1971, Small walked through the airport in San Francisco and people were spitting on the soldiers.

“The anti-war thing was real strong,” he said. “They were blaming it on 20-year-old kids. What did they have to do with it? They were just doing what they were told.”

With the war winding down, Small decided it was time to leave the military.

“The Army is good duty during wartime, but it sucks during peace time,” he said. “I didn’t want to get assigned some bullsh-t job somewhere. So I decided to get out. The outfit I wound up in, there was a real good chance I’d wind up being a big general. I had done well.”

Small spoke as if he had gone through his military experience wrapped in an impenetrable bubble. He practically scoffed at jungle firefights. Kathy Dibben, who worked closely with Small as his assistant and exercise rider in two separate phases of his career, heard differently.

“He told me he tried to get himself killed in Vietnam by, you know — ‘I’ll do it! Behind enemy lines? I’ll go!’ Why? I don’t think he ever liked his dad,” Dibben said. “He would have stayed in. He tried to re-up for another year, but they were going to send him stateside and put him behind a desk, so he went back [home].”

On Sept. 12, 2001, the day after Al-Qaeda terrorists took down the World Trade Center in New York, flew a hijacked plane into the Pentagon and crashed another plane in a Pennsylvania field, Small — at age 55 — attempted to re-enlist.

United Airlines Flight 175 crashes into the south tower of the World Trade Center complex in New York City during the September 11 attacks Robert J. Fisch/Wikimedia Commons

“I was old,” he said. “I thought I’d just free up somebody. I thought there was going to be a world war, to tell you the truth. I thought everybody was going to have to go in anyway, so I might as well get in first. It was sort of a selfish thing.”

Small said a master sergeant at Fort Meade encouraged him at first, but soon Small received a phone call telling him thanks, but no.

“I went up and saw my dad,” Small said. “He was at the farm, retired. His health wasn’t that good. He said his own father had done the same thing when World War II came. He had been in World War I, and he went to re-enlist in World War II. He was a civilian employee at Pearl Harbor when it got bombed. He was a desk guy.”

Becoming a Trainer

Small took his time heading home after Vietnam. “I was kind of lost,” he said, “and took a couple detours.”

He finally made his way back to Baltimore and caught a ride down to Pimlico one morning, still wearing his uniform, short of civilian clothes.

“The first person I saw was Harry Jeffra,” Small said, referring to the Hall of Fame boxer who ruled the bantamweight division in the late 1930s. “When he retired, he became a stall man. I’d known him my whole life. He grew up in that neighborhood. He was the first person I saw. I thought, ‘Now, I really am home.’ ”

Small’s return did not go smoothly. He married Ann Merryman, also a trainer, whose family traced back to 1600s Virginia and had become extremely prominent in the tight-knit Maryland Thoroughbred world. Her father had bred the star filly Twixt and had been a fighter pilot in World War II, but shared roots didn’t help the couple get along any better and they quickly divorced. Bitter, Small never married again.

“Everything I had done in my life was a good move except that,” he said.

Small’s mother, meanwhile, was agonizingly dying of cancer.

Dickie idolized his mother, Jane Small (center), but had a rougher relationship with his father, Doug Small Sr. (right), shown here with Dr. Janon Fisher (left) Arthur Kunkel

“[Dickie] idolized his mom,” Dibben said. “She was bedridden a long time. The cancer treatments were hard on her. He said she could run the farm from her sick room window better than anyone ever did from the ground because she could look out and see a yearling right out in the field and [spot a problem]. So … she was the horsewoman he idolized.”

Small, after taking out his trainer’s license in 1974, had been helping his father at the races. One afternoon they were at Monmouth Park running a horse, and the owner had friends with him — John and Sally Gibson of Drumore, Pa. Small ate lunch with them, and they hit it off.

The Gibsons, Small said, raced horses with trainer Billy Dixon. They got in a fight with Dixon’s girlfriend, the jockey Vey Martini, who was demanding to ride first call on their runners. It severed the relationship, and Small received a phone call asking him to take over.

His father, meantime, soon would be fired by his most important client, Ben Cohen — longtime owner of Pimlico Race Course. When Cohen fired Doug Small Sr. in the spring of 1976, the owner sent seven grooms with seven shanks down to lead the horses over to the barn of future Hall of Famer Bud Delp. Cohen’s mares and babies, whom the Smalls had helped foal and raised, remained on the family farm.

When time came, the yearlings were prepared for auction. Before she died, Jane Watters Small told her son one of them — a filly — was special, the final one she had delivered before cancer forced her to bed.

Sally Gibson wanted a yearling, and her new trainer went to the sale at the Timonium Fairgrounds and waited to buy the one his mother liked. The gavel came down at $12,000. The filly’s name was Caesar’s Wish.

Before Caesar’s Wish, Small had already shown his prowess after taking out his trainer’s license in 1974 with a classy but struggling gelding named Festive Mood. With the help of a young jockey named Herbie Hinojosa, Small figured out the horse needed to be trained really, really hard.

“So we did, and the next thing you know, he wins the (John B.) Campbell (gr. II at Bowie),” Small said. “The Campbell in those days was like the Jockey Club Gold Cup. It was a big deal.”

Festive Mood (inside) wins the 1976 John B. Campbell Blood-Horse Library

After the 1976 Campbell win, Small’s first graded stakes score, Festive Mood had a steady summer campaign traveling to stakes races. Then the horse received an invitation to the $350,000 Champions Invitational Handicap, a grade I event in November 1976 at Santa Anita.

Small said, “Let’s go do it,” but his father became furious with him. Why go all the way to California and run against killers at 50-1, when he could stay home and be 4-5 in a $50,000 race?

“We get out there and just miss,” Small said. “He’s up on the pace. He went three-quarters in 1:09 and something, and he keeps on going… Shoemaker and Whittingham come from left field on a horse called King Pellinore and beat him right on the money.”

Festive Mood ran through the following year at age 8, and that race in California showed Small that he could take a horse onto the grand stage, just in time for Caesar’s Wish.

Bernie Bond, who trained seemingly forever at Pimlico, had a speedy filly named Luck Penny, who opened her 1977 campaign with three straight victories before meeting defeat in the grade I Monmouth Oaks. Bond worked all his horses fast, Wednesdays and Saturdays, whether they needed it or not.

“Bernie put the hammer down,” Small said. “The clocker would always say, ‘Fifty-eight and change,’ and he’d say, ‘You can keep the change.’ ”

One morning early that spring, Small got on his pony and went out to watch Caesar’s Wish work. She was born June 1 so in reality was still just a yearling.

“I had gotten one of those good Guinand stopwatches, Swiss jeweled, and [Luck Penny] went in :46 [seconds],” Small said. “I thought, ‘Jesus Christ,’ but this is a fast horse and the track is pretty fast. So, now, it’s this little baby. She’s only been a half-mile once or twice. So Kathy [Dibben] worked her, and she’s not a jock; she’s an exercise girl and not that small. Anyway, the filly went in :46. I thought, ‘Something’s wrong with the watch.’

“I’m down at the seven-eighths pole at Pimlico and I threw the watch out in the parking lot — and Guinand is one of the good ones. I threw it out, and it’s in a million pieces. It looked like she was just cantering.”

Small bought a cheaper stopwatch, and the following week he clocked Caesar’s Wish working five furlongs in :59. He kept that one.

On May 25, Caesar’s Wish debuted at Pimlico like a gust of wind, finishing a fifth of a second off the track record for 5½ furlongs. Jockey Danny Wright “was pulling her up because the rest of the fillies were still coming around the quarter pole,” Dibben said.

Caesar’s Wish then won the Toddler Stakes at Bowie Race Track but came out of the race with a minor fracture that cost her a summer campaign. She returned to the races at Keystone Race Track (now Parx Racing) and won an allowance. On a return to that Philadelphia track for a stakes race two weeks later, Small and Dibben suffered a flat tire and spent two hours in a gas station with the filly ready to detonate in the trailer. Caesar’s Wish finished fifth that day.

The Breeders’ Cup World Championships didn’t exist at the time, and perhaps the most important race on the East Coast for 2-year-old fillies in the fall was the Demoiselle Stakes (gr. II), at a mile and an eighth at Aqueduct Racetrack.

Caesar’s Wish won the Tempted Stakes at a mile as a tune-up and then went to the Demoiselle. In her absence that summer, a filly named Lakeville Miss had taken three straight grade I events on her way to a division championship. With Wright aboard, Caesar’s Wish showed just what that minor fracture had cost her.

“We went up for that race and just blew her doors off,” Small remarked.

Small had not yet begun to winter at the Fair Grounds in New Orleans or at Oaklawn Park in Arkansas, so he kept Caesar’s Wish in training at Pimlico. Winter training was difficult but not impossible. As regimented and detail-oriented as Small was from the Army, he also knew how to improvise. A January blizzard closed Pimlico for training, yet Small told Dibben to meet him at the track at 2 o’clock one morning.

Former assistant Kathleen Dibben on the pressure of working for Small in the early days Milt Toby Photo

They arrived to find a snowy stillness. A brilliant moon reflected off a three-inch blanket of white covering the track and lit up the grounds. Small cut the padlock to get onto the course, and Dibben galloped Caesar’s Wish, who loved the feel of the snow hitting her belly.

Afterward, they cooled the filly out at trainer Kenny Fields’ barn to create misleading footprints. Somebody had to take the blame for the broken padlock.

Despite the adventures riding high with good horses, Dibben said Small could be a terror.

“When he was mad and he’d get to drinking, he was a scary son of a gun,” she said. “It was only Caesar’s Wish that kept me at the job.”

In the next sentence, however, Dibben gave credit to Small for giving up alcohol for the final 25 years of his life. She expressed unbound admiration for her former employer.

“His horses, because he’s not a drug trainer, they (got) good care, and they never raced on anything,” she said. “I don’t even remember giving Bute the day before. Caesar’s Wish didn’t get anything.”

Small admitted he could be tough, but he had his reasons. The good of the horse always came first.

“I learned a lot in the military schools about how to manage and get things done,” he said. “Everybody laughs at the military, but there is a reason for everything we do, and everybody who worked for me would know this is the way we do it. Then somebody would put a horse in jeopardy… just one little thing — put the shank on wrong — that was when I’d lose my temper.”

Caesar’s Wish opened her 3-year-old season in 1978 with a second in the Busanda Stakes at Aqueduct and then won the Searching Stakes there and the Hilltop Stakes at Pimlico. Small’s plan was to skip the Kentucky Oaks (gr. I) and win the Black-Eyed Susan Stakes (gr. II) back at Pimlico, his home track, in front of everyone he knew.

In the last week of April, Caesar’s Wish worked a mile with another horse in 1:36 and dragged Dibben around the barn cooling out. Small looked at his filly and told his assistant to go home and pack her bag for Kentucky.

This improvisational trip didn’t work out well. Small drove for four hours, nursing a cooler of beer, according to Dibben. He eventually climbed in the back to sleep, and she took over.

“The highway in West Virginia isn’t even finished,” Dibben recalled. “I’m going along, and I don’t see lights for hours. I’ve got a million-dollar horse in the back, my boss is passed out, and then we start running out of gas.”

Bob Coglianese/NYRA
Milt Toby
Milt Toby
Top: Caesar’s Wish wins the 1978 Searching Stakes; Left: takes the 1978 Black-Eyed Susan Stakes (gr. II); Right: breaks Ruffian’s record for a mile and an eighth, blitzing the 1978 Mother Goose Stakes (gr. I) in 1:47.60

Small, however, had packed a five-gallon gas can that got them through the mountains. What he couldn’t plan on was arriving at Churchill Downs and drawing post position 13 for the Oaks in a race full of other speed horses. Caesar’s Wish was stuck wide on the turns the entire way around and came in fifth.

“It was probably the worst finish in her whole life,” Dibben said.

The Oaks, however, took nothing out of Caesar’s Wish. She returned to Maryland for a triumphant victory in the Black-Eyed Susan — her original target all along — then went to New York for the grade I Mother Goose Stakes the day after the Belmont Stakes (gr. I).

Traveling with Caesar’s Wish that spring, Small and Dibben had been treated to the three epic Triple Crown confrontations between Affirmed and Alydar. Now it was time for their command performance. With Wright never raising his whip, Caesar’s Wish went straight to the front in the Mother Goose.

Dibben still has a sequence of photographs from the race, where Lakeville Miss drew even with their front-runner.

“Danny goes like this,” Dibben said, snapping her fingers, “and she’s gone. That was amazing, and she did it like it was nothing.”

With a time of 1:47.60 for a mile and an eighth, Caesar’s Wish broke a stakes record set by the legendary Ruffian. Suddenly, a championship appeared within reach. No other filly could keep up with Small’s horse.

The stars of the division assembled at Belmont Park for the grade I Coaching Club American Oaks at a mile and a half: Caesar’s Wish, Kentucky Oaks winner White Star Line, Lakeville Miss, and Acorn Stakes (gr. I) winner Tempest Queen. Completing the field was a completely overmatched runner named A Grey Jet, who doomed the chances of Caesar’s Wish.

Early in the race the jockey fell off of A Grey Jet, and the riderless runner hounded Small’s filly, the 8-5 favorite, around the giant Belmont oval. Caesar’s Wish never caught a breather, and Lakeville Miss passed her and drew away to win by six lengths.

The historic Alabama Stakes (gr. I) on Aug. 12 would decide the divisional championship. The leading runners were all in attendance. Small took Caesar’s Wish to Saratoga, where she bedded down in his uncle’s barn. The day of the race, he could not have been more thrilled. Rain poured down, soaking the old track, and he knew Caesar’s Wish loved running in the mud.

At a mile and an eighth, Caesar’s Wish would attempt to control the Alabama from start to finish. The sloppy conditions only enhanced her chances, and she went straight to the lead under Wright. Longshot Dungarven attempted to match her strides and quickly disappeared from contention.

Down the backside Caesar’s Wish galloped — “like she’s floating,” Small said — but with three-eighths of a mile to go, Tempest Queen had suddenly closed in. Wright went to the whip, and Caesar’s Wish began to stagger, only her momentum carrying her to the top of the stretch.

Wright jumped off before she fell and knelt down beside the stricken filly, beating on her chest. A pony girl saw Dibben splashing panicked through the sloppy track and let her take her horse to get to Caesar’s Wish. When Dibben arrived, the filly’s lips were white and her tongue hung out. She had burst a pulmonary artery and died.

“I went down there,” Small said, telling the story but keeping his emotions at bay. “Went in the ambulance with her, and that was the end of that.”

Small’s tight circle was sent reeling. His mother had died that spring. Dibben, traumatized by the loss, soon quit and moved to South Carolina. His groom suffered a nervous breakdown, and Small didn’t see her again for five years.

Telling her version of the story one morning over breakfast at a diner north of Baltimore 36 years later, Dibben began to cry softly.

“I kept her halter,” she said as others at the table shared in this old grief. “I still have the nameplate from it and some tail hairs. They’re in my album. That was the horse of my life. I’ll never be around another one like that.”

In the immediate aftermath Small told the Daily Racing Form, “I guess the worst thing was when we were packing up to leave Saratoga. All we had was some buckets and things. We didn’t have any horse to load.

“But it wasn’t the worst thing in the world. It wasn’t like the guy next to you getting blown apart, and you’re the lieutenant and you have to wonder whether you could have protected him.”

Despite the setback, “I just kept going,” Small said, with a soldier’s resolve. He raced horses exactly how he wanted, developing them from yearlings and seeing if they could make the grade.

Only once in his entire career did Small claim a horse: In the late 1970s he adored a cheap old gelding named Can Gun and ran him for a low price to get him eligible for starter allowance races. King Leatherbury claimed Can Gun, and Small claimed him right back and retired him.

He went the next seven years after the death of Caesar’s Wish buying yearlings at Timonium for Sally Gibson and a few other owners and winning lots of stakes — until one day he received a call in 1985 from Robert Meyerhoff, the philanthropist, art collector, and breeder, who is one of the richest men in Maryland.

Meyerhoff’s trainer, Tommy Field, had recently passed away, and the owner decided to divide 20 young horses among three trainers — Small, Bill Boniface, and John Forbes.

Small drove out to Meyerhoff’s 300-acre farm in Phoenix, Md., and saw eight or nine unraced 2-year-olds in a pen. With the sharp eye of his mother, Small knew right away which one he coveted.

“As soon as I saw him, I said, ‘Oh, sh-t. This one is different,’” Small said.

Dickie Small immediately recognized Broad Brush as a talented athlete Anne Eberhardt

Meyerhoff had begun to build an imposing band of broodmares, and one was Hay Patcher, a stakes-placed daughter of Hoist the Flag, who became the foundation of his entire operation. He bred her to Ack Ack, a Horse of the Year on the track but an afterthought as a stallion.

The union produced Broad Brush.

If Caesar’s Wish had been Small’s greatest runner, Broad Brush proved his greatest challenge. The colt was unfathomable, housing a screwball mind inside the body of a monster. Yet he could be devastating, earning 12 stakes wins — four in grade I races — at 10 different racetracks around the country.

Asked which was better, Small said, “Caesar’s Wish was really, really fast. She might have beat him up to a mile.”

Kathleen Dibben

Learned much from Small, including a knack for figuring out tricky horses

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Small recalled early on in Broad Brush’s training watching him gallop down the backside under exercise rider Anne Wolff and, for no apparent reason, just stopping cold. His talent was unmistakable, but Small had to devise little tricks each morning just to get his colt to train. While Broad Brush streaked to six victories in his first eight starts, the outings sometimes seemed like comedy routines.

Of Broad Brush’s victory in the 1986 Jim Beam Stakes, Bill Christine wrote in the Los Angeles Times: “Broad Brush acted then as though he had been nipping at some of the race sponsor’s product in the final yards… he ducked out, then weaved in, not unlike a tosspot on New Year’s Eve, but still hung on to win.”

Broad Brush pulled the same stunt in the Wood Memorial and won that, too.

“I can’t think of anybody crazy enough to have trained him,” Small said, laughing at the thought. “They wouldn’t have had time to do it. I had a fairly big stable. The boss sent me 10 horses. I told him what I was doing with Broad Brush, but I ruined the other nine training him. I said, ‘Boss, these are just horses.’ We ground them up.

Broad Brush (no. 3) wins the 1986 Wood MemorialSkip Dickstein
Broad Brush settled for third in the Kentucky Derby, behind Ferdinand and Snow Chief E. Martin Jessee/Keeneland

“I had him at Belmont one day with Sidney, and I asked him if he had something to gallop with him. He said, ‘Oh, I’ve got a nice colt.’ They galloped once around Belmont, and Sidney said the horse laid down and was never worth a nickel after that. Just galloping with [Broad Brush] one day completely ruined him.”

In the 1986 Kentucky Derby (gr. I), Broad Brush dueled with the California star Snow Chief at the top of the stretch, but Bill Shoemaker ambushed them both with a perfectly timed attack on Ferdinand, and Small’s contender had to settle for third. In the Preakness, Snow Chief used his speed advantage and took the inside route home, and Broad Brush never could catch up. He was third again.

After skipping the Belmont Stakes to win the Ohio Derby (gr. II), Broad Brush ran in everything — the St. Paul Derby, The Haskell Invitational (gr. I), the Travers Stakes (gr. I), and the Pegasus Stakes (gr. II). His victory in the Pennsylvania Derby (gr. II) on Sep. 27 proved to be his wildest.

Against a field of inferior rivals over a sloppy track, the big bay colt tracked the pace in the clear on the outside for half a mile before jockey Angel Cordero Jr. sent him to take on the frontrunner, Glow. The two battled to the five-sixteenths pole, where Broad Brush put five lengths between them.

Watch Broad Brush’s antics in the 1986 Pennyslvania Derby (gr. II)

Broad Brush, however, couldn’t be bothered with the far turn. He careened sideways like a tap-dancer on stage beating it into the wings, nearly disappearing into the chute that extended off the top of the stretch. The other horses, suddenly full of good fortune, continued battling as he paid a visit to the outside rail. Somehow Cordero, a masterful rider, recovered and set Broad Brush straight. With ears pinned, the colt surged from fifth to first in a blur of giant strides and won clear of the field.

Broad Brush closed out his 3-year-old season beating older horses in the grade I Meadowlands Cup, and Small set his sights on the Santa Anita Handicap (gr. I) and a rematch with Ferdinand and Snow Chief the following year. Along the way he discovered the secret to soothing his savage beast. As King Kong had Fay Wray, Broad Brush had his van rides.

Since there was no giving Broad Brush days off from training, if Pimlico was closed, Small would drive the colt to Laurel or Bowie. The rides and scenery engaged Broad Brush and took the edge off his crotchety nature. Sportswriters took the story and ran with it when they discovered Small personally had driven Broad Brush the 12 hours from Baltimore to Louisville for the Kentucky Derby. Who else should the trainer trust with such valuable cargo? Yet Small took his chauffeuring duties to bewildering heights.

“I’d put him in the back and go to the bank, go to the post office, go to the store,” he said, clearly enjoying memories of the mischief. “He would just look out. I’d get back around feeding time, put him in, and the next morning he was bucking and kicking. If I needed to sleep or needed a rest, I’d take him to the airport. I’d sleep in the front, and he’d watch the planes for a couple hours.”

Watch Broad Brush edge Ferdinand in the 1987 Santa Anita Handicap thriller

In January 1987, Small flew Broad Brush to California for the big three-race series at Santa Anita — the San Fernando Stakes, the Strub Stakes, and the Santa Anita Handicap.

In the first race Broad Brush easily handled Ferdinand and Snow Chief, but once he made the lead, he eased up. Variety Road, with Laffit Pincay Jr. in the irons, beat him in a photo finish.

Small decided to stay in California to train for the second race instead of returning home. The only other horse he had out there was an old mare named Flow and Flux, who, while much slower, was one of the few horses who could withstand the rigors of galloping with Broad Brush every morning. Small figured his runner needed to work a mile in 1:37 in order to be at his best for the Strub. In the key workout before the race, the trainer started Flow and Flux well out in front of Broad Brush, thinking he’d buckle down and go get her.

“He knew who it was, and he didn’t catch her,” Small said. “So, instead of working in 1:36 and change, he worked in 1:42. That was wide open for Flow. That was as fast as she could go. He gets in the race and Snow Chief and Ferdinand beat him.”

Back in Baltimore, Meyerhoff grew gloomy at the back-to-back defeats, so Small leveled with him.

“I said, ‘Boss, you’ve got two choices — buy a stakes horse to work with him here, or I’m going to have to take him back to Pimlico to get him ready for this next race. ‘He said, ‘What kind of horse do you mean?’ I said, ‘A stakes horse, and it’s going to cost a lot of money. An ordinary horse isn’t going to do it. We’ve already got one of those.’ ”

Meyerhoff balked at purchasing an expensive sparring partner, and Small flew Broad Brush back to Pimlico and set him to work against a relay team from his own barn.

“I’d work him a mile,” Small said. “One horse would start off with him and go all the way around to the half-mile pole and then pull up. Then I’d have another horse on the turn go the last three-eighths and hook him and make him really work, and they’re both stakes horses. I needed two of them, you know?”

Broad Brush showed up fit and ready for the 50th running of the $1 million Big Cap before more than 67,000 fans.

Telling the story one day last winter, Small pulled himself up in his truck to make sure he made himself clear.

“It was one of the best races ever,” he said. “If you’ve got a list of the top 10 races, it’s one of them.”

Charlie Whittingham on the 1987 Santa Anita Handicap broadcast

Charlie Whittingham, who trained Ferdinand, was worried about the freewheeling Snow Chief having everything his own way on the lead of the mile-and-a-quarter race, so he entered a “rabbit” called Epidaurus to set things up for his late-runner. Small didn’t mind; softening up Snow Chief would help Broad Brush, too.

“The night before, I’m sitting in the motel watching TV, and Whittingham and Shoemaker come on,” Small said. “They cut it off in the Youtube version, but the last thing Whittingham says is, ‘But the guy in the bib overalls’ [which Small liked to wear at times] ‘might have the best horse.’ ”

Epidaurus did his job at the start, pressing Snow Chief from the outside through a swift first quarter-mile, with Ferdinand racing five lengths behind and Broad Brush five more back. Midway down the backstretch Gary Stevens sent long shot Bedside Promise on a dash to the leaders, and Ferdinand followed on his outside.

Overwhelmed by the pace, Epidaurus fell away, and the three leaders hurtled into the turn while Cordero and Broad Brush began to make up ground. Rounding for home, Shoemaker and Ferdinand took over and just as quickly, Broad Brush was locked to his side.

“For a sixteenth of a mile, their feet are like exactly the same,” Small said of the battle that led to a photo finish. “So they put the numbers up after what seemed like a half an hour. I said [to my brother, Steven], ‘Who’s the 3?’ And it was us.”

Immediately after the race Broad Brush looked ready for another, and Small and his brother had to get a shank on both sides of him just to get him back to the barn.

“That’s what kind of horse this was,” Small said. “This horse was different. He was just unbelievable. I was scared to give him Lasix. I was afraid they’d never get him to stop.”

Concern returns victorious to the winner’s circle after the 1994 Breeders’ Cup Classic (gr. I) Skip Dickstein

Broad Brush ran six more times that year, and Meyerhoff retired him to a stud career that is credited with rescuing an endangered Thoroughbred bloodline tracing back to Domino.

Racing mostly Broad Brush babies, the Meyerhoff-Small team went on a tear that lasted nearly two decades, one stakes horse after another, and was capped by Broad Brush’s little son Concern winning the 1994 Breeders’ Cup Classic.

“It was unbelievable,” Small said. “All we had to do was point them in the right direction, and they were going to win. You might get them in a race that was too strong, and they wouldn’t win, but they did the best they could. Once you get them in the right race, they win.”

Over time, however, the well eventually ran dry, as almost all do. Concern wasn’t a quarter of the sire Broad Brush was.

Kathleen Dibben

Said Small almost always knew which horses to keep and which to move on

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“I had all these [Concern] 2-year-olds, and [Meyerhoff] said, ‘You’ve got to get them in front,’ ” Small said of the decline. “And I said, ‘The Holy Ghost couldn’t get them in front.’ ”

If Caesar’s Wish hadn’t dropped dead in the Alabama, if Small hadn’t temporarily split with Meyerhoff in 1999 in the face of mounting defeats (which cost him the opportunity to train handicap star Include), if he hadn’t later lost top runners Richard’s Kid and Delaunay to other trainers, Small might already be in the National Racing Hall of Fame.

Maryland Jockey Club racing secretary Georganne Hale respects Small’s accomplishments in his home state

From 1976 to 2014, he won at least one stakes race every year except four. In that span he trained 20 different graded stakes winners, not one of them inherited from another outfit. He captured 218 total stakes, 36 of them graded black type, the highest levels of racing in the country. In 1994 he sent out 10 different stakes winners.

Yet getting into the Hall of Fame did not appear to interest him much, even into his final months.

“It’s truly not something that’s important,” Small said on another gloomy morning at Laurel. “My mother, my uncle, all the people I grew up with, who would say, ‘That’s really cool,’ they’re all dead.”

Those who worked with him seemed to adore Small despite his coarser sides. Dylan Smith, his final assistant, was intimidated by his reputation when she first started in 2013 — but she also said her own inexperience played a part.

“…I had never worked at the track before,” she said. “It had been like summers, hot-walking, but I had never galloped. That was all very new to me. It was a little intimidating at the beginning, but you can’t be intimidated at the track if you want to do well.

“I heard he was kind of angry and very difficult to get along with, but, of course, those were all from people that maybe didn’t work out with him.”

Georganne Hale

Fashion Police

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Georganne Hale, the Laurel Park and Pimlico racing secretary, laughed with glee telling a story about how Small once threw a new sports jacket under a tractor harrowing the track at Laurel because someone in the racing office made a crack about it.

She said she understood his short fuse because, perhaps as a nod to his military roots, he did not tolerate fools.

One late winter morning at Laurel, well into Small’s final months, Smith climbed aboard Broad Rule — her favorite horse in the barn — and set off for a morning gallop. The graded stakes-placed Meyerhoff homebred, a multiple stakes winner without a drop of Broad Brush blood in his pedigree, was the outfit’s best thing going for two years.

In mid-March, Small moved his stable from Laurel to his long-time favorite barn at Pimlico. At the time he was carrying approximately 24 runners, with new 2-year-olds on their way in. Most were owned by Meyerhoff and himself.

Smith said after completing her barn chores that there was a misperception around the track that she ran the whole show for Small in his final days. That couldn’t have been further from the truth.

“Last summer was when he got real sick for awhile, and he ended up in the hospital and then he had to stay home for awhile; that’s when I had to really step up and try and keep things going,” she said. “When he was in the hospital, I pretty much had to make all the decisions. But he still comes out here and watches… sometimes people get the wrong impression that I’m running the stable, but he’s still very much active and on top of everything. He’s the man.”

Back in the parking lot, Small was tired but talking.

“For every good bounce is a bad bounce, and when you get a good bounce, you have to be able to recognize it — and a lot of people don’t,” he said. “A lot of people get a real good horse and don’t really help them. They get to thinking it had something to do with them.”

Broad Rule galloped by, and Small said he looked ready for his upcoming stakes assignment. He knew his own next assignment was the same as it was after Caesar’s Wish died — just keep going.

“I pretty much come down here and it takes me the rest of the day to get ready to come back again the next day,” he said, rubbing his forehead. “I get really, really tired. I go home, get something to eat, and rest. This is where I am. I’m here every morning.”

Dickie & Broad Rule Jim McCue
Bill Mooney
Anne M. Eberhardt
Skip Dickstein
Dylan & Dickie Jim McCue
Anne M. Eberhardt
Throughout the years, Small remained a vibrant member of the Maryland racing community

Dickie Small passed away April 4 at the age of 68. That afternoon Dylan Smith put the saddle on his final runner, a 3-year-old Maryland-bred filly named Sawitinyoureyes. She finished seventh in a maiden special weight race at Pimlico.

A memorial was held five days later at Saint James Episcopal Church in Monkton.

The little brick church dates to 1755, and the graveyard surrounding it is filled with ancient headstones bearing the name Hutchins — Small’s ancestors.

The pews were filled with family, friends, horsemen, and former employees; Rosie Napravnik took off her mounts at Keeneland and flew in to pay her respects. She, like many other young female jockeys and exercise riders, got her first break at the track with Small.

Meyerhoff, long his principal client, said he hadn’t decided what would become of his horses that had been in Small’s care.

“He was a close personal friend, not just a trainer,” Meyerhoff said. “We spoke two or three times a week for 30, 40 years. People that want to go into the horse racing business sometimes ask me for advice. I say, ‘First, pick out a trainer you enjoy being with, because you spend a lot of time with the trainer and not a lot of time in the winner’s circle.’ ”

At the Hunt Club reception that followed, a video loop replayed a few old races. There was Small, in a bowtie and one of those floppy fedoras he loved, with his brother Stephen, leading Broad Brush into the winner’s circle after the spectacular photo finish victory in the Santa Anita Handicap.

“The clichés all break down with Dickie,” writer and close friend Patrick Smithwick said during his eulogy. “ ‘Oh, he was the guy who thought the glass was half full,’ one might say. If you knew him, you knew that was wrong. The glass was flat-out overflowing, brimming, bubbling over.”