This is a three-part series following the difficult path along the 2019 Kentucky Derby trail of three hopeful trainers, jockeys and horses — Knicks Go, Well Defined and Win Win Win. Join the journey of relative outsiders making a run for the roses. View the second story in the series here and the third and final story here.

TAMPA, Fla. – Roars cascaded in the distance as Kathleen O’Connell relaxed in a chair outside Barn 25 on the backside of Tampa Bay Downs.

She didn’t sleep there the night before, and the admission wasn’t meant as a joke. That has been known to happen.

As horse trainers go, O’Connell might be the most hands-on, a “control freak,” in her words. Others around the track say she's a workaholic. They also say she’s the best around.

Her barn, a peaceful respite amid the dirt and urgency of the backside, feels like a hangout spot. There's a lawn jockey, and a sign that dates its establishment back to 1981. Workers ride by on bicycles, speaking to horsemen and jockeys seated out front enjoying conversation and nice weather.

Let's Talk Derby:New video series answers your top questions about Kentucky Derby

Part 2:Jockeys hustle for years to rein in a horse golden enough for the Kentucky Derby

It’s hectic in the mornings, but this was a Saturday afternoon. Birds chirped. Horses shuffled in their stalls. The grandstand packed with racegoers on the other side of the track felt far away, the Kentucky Derby even farther, though neither was out of reach.

A Michigan native who headed to Florida long ago, O’Connell — or “K.O.” — is an institution here. She has won more than 2,000 races in a career that spans decades.

But she's only sent one horse into the gate at the Kentucky Derby.

Perhaps that was about to change. O’Connell stood and walked down a pathway of her horses. One of the more promising 3-year-olds in the country was delighted to see her, immediately peeking his head out of his stall.

“No, I didn’t bring any candy for you,” O’Connell told Well Defined, stroking his head.

The points system that determines the field of 3-year-old horses each year in the Kentucky Derby was implemented prior to the 2013 edition of the race, replacing an old qualification system that used graded-stakes earnings.

Of the 366 horses nominated to run in Triple Crown races in 2019, only 20 — fewer than 6% — will earn enough points through results in 46 prep races to make the cut and Run for the Roses the first Saturday in May, with the possibility of an alternate making it in with a late scratch.

In order to make it, you not only have to have a great horse, “You have to be lucky,” said O’Connell. “The stars, the moon and the sun all have to align perfectly.”

Part 3:By a nose: Making or missing the Kentucky Derby can be decided in a split second

The sport's most prominent trainers routinely reach the Derby with the system because they have more quality 3-year-olds in the hunt. It's far tougher for the little guy. Owners, jockeys and trainers like O’Connell, those who have little to no experience in the Derby, might go years without a horse good enough to do it.

So strategically they pick and choose when and where to run for the best shot at qualifying. It’s complicated and can change in an instant. One minor injury or poor performance can, and often does, end Derby dreams.

Well Defined, usually housed in O’Connell’s other base near Miami, had come to Tampa on business.

He’d won one Derby prep race already, but since that one didn’t earn enough points to qualify, it simply raised expectations, setting the stage for the day's pivotal Tampa Bay Derby.

The next race was worth more points. Winning it would ensure his spot at Churchill Downs on the first Saturday in May.

By the looks of it, Well Defined was ready to get his points. And some candy, too.

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No longer the underdog

“What just happened?” exclaimed NBC commentator Laffit Pincay III after a 70-1 longshot named Knicks Go wired the field to win October’s Grade 1 Breeders’ Futurity at Keeneland by 5 ½ lengths.

The winning horse’s ecstatic trainer, Ben Colebrook, was asked a similar question by Keeneland’s host while celebrating his and jockey Albin Jimenez’s first-ever Grade 1 stakes victory.

“Just got lucky,” Colebrook replied with the delighted chuckle of a man who'd happened to pick the correct lottery numbers.

A good-natured, affable son of Kentucky horseman John Colebrook and a former student at the University of Kentucky, Ben Colebrook was raised around horses. He turned 41 in March, having struck out on his own as a trainer in 2012 after being mentored by trainer Christophe Clement.

Colebrook, based at Keeneland, had trained some well-known horses already, most notably Limousine Liberal, two-time winner of the Grade 2 Churchill Downs Stakes on the Kentucky Derby undercard.

With Knicks Go, however, Colebrook was heading on the Derby Trail for the first time.

Racing really didn’t know what to make of Knicks Go. His was a heck of an underdog story. Those odds were a dead giveaway to the story playing out. The Maryland-bred son of Paynter didn’t have a big-time pedigree. He resembled an ugly duckling compared with other sculpted thoroughbreds. He was owned by the Korea Racing Authority, a relative lightweight in the business.

Even his name was misunderstood. It didn’t have anything to do with the NBA’s New York Knicks and instead was tied to genetic “nicking” software used to select horses. The “K” was added as a preference by the Korean ownership.

“KAY-nicks” might be the correct pronunciation, but hardly anyone says it like that, including the Keeneland track announcer floored by the 2-year-old’s performance in the Futurity, a win-and-you’re-in race for the Breeders’ Cup Juvenile at Churchill Downs.

At 40-1 odds there, Knicks Go produced another stunning effort for Colebrook and Jimenez. He led a 13-horse field entering the stretch before losing the duel to Game Winner, the Bob Baffert-trained, even-money favorite.

Read more:Bob Baffert has top 3 horses in the Kentucky Derby Media Poll

Knicks Go’s days as a longshot were over. His Derby Trail journey had started.

“I know people kind of viewed the race at Keeneland as a fluke,” Colebrook said later, “but I didn’t really think it was a fluke. He’d trained like a good horse. I don’t want to say we were confident, but we thought we had a decent shot in the (Breeders’ Cup) race.”

The Futurity win and second-place Breeders’ Cup showing had spotted Colebrook 18 early Derby points (30 generally gets you in the conversation, while more than 40 would be viewed as safe).

Now the pressure was going to be different, he soon learned, as was the attention.

“You just don’t realize how much — maybe limelight is not the right word — but just every little thing is closely monitored with these Derby horses,” Colebrook said, “where even with a horse like Limousine Liberal, everything I do, nobody really cares.”

Colebrook is based at Keeneland, but he has an operation at Tampa Bay Downs, leaving him traveling frequently between the two spots during the winter.

The spring path designed for Knicks Go would be the warmer one. The horse was stationed for the winter in Tampa, pointed toward the two Derby points races there — the Feb. 9 Sam F. Davis (worth 10 points to the winner) and the March 9 Tampa Bay Derby (worth 50 to the winner).

Knicks Go would be the morning-line favorite entering the Sam F. Davis.

In some ways, though, he still seemed like an underdog.

See also:Jockeys say whips necessary for their safety and that of the horses

An exclusive club

For all the accomplished trainers throughout the world, the Kentucky Derby has become an exclusive club.

Of the 97 horses that have reached the starting gate in the Kentucky Derby the past five years, 48 — nearly half — were trained by one of seven people: Todd Pletcher (16), Steve Asmussen (7), Bob Baffert (6), Dale Romans (6), Michael Maker (5), Chad Brown (4) or Mark Casse (4).

Only 16 trainers have had more than one Kentucky Derby starter during those years.

“Guys like me don’t really get a chance (with) Derby horses,” Colebrook said. “If I had one every 10 years, it’d probably be a lot. My career has not been going very long. … A lot of those Derby horses, they go to people that have a track record of getting to the Derby every year, which is probably well-deserved. I mean, if you’re an owner and you’ve got a horse that looks like a Derby horse as an early 2-year-old, you’re probably thinking you’re going to go to Bob Baffert or Todd Pletcher.”

“The era now, and nothing against Bob Baffert, but he gets million-dollar pedigrees and he gets so many, he can siphon through them all,” said Richard Grunder, the track announcer at Tampa Bay Downs. “… Unfortunately, it’s kind of the way racing is going. Seems like, you can just look at trainer standings, and it’s the haves and the have-nots.”

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O’Connell’s lone Kentucky Derby was in 2011 with Watch Me Go, a Tampa Bay Derby winner who drew the No. 20 post and finished 18th of the 19 horses in the Kentucky Derby won by Graham Motion’s Animal Kingdom.

At the time, headlines about O’Connell’s bid at Churchill Downs had to do with her vying to become the first female trainer to win a Kentucky Derby.

It’s a storyline that she still shrugs off without much thought.

“It’s not even in the realm of things,” she said. “That horse doesn’t know if I’m a boy or a girl. I still have my very first (riding) license that says, ‘pony boy,’ because there was no girl categories. …

“There’s a lot of good trainers in this business. There’s a lot of underrated trainers in this business. But I think the (Triple Crown) focus is on the people that do have the most experience and have had the most horses, and the people that are investing a large sum of money and trying to go with who’s had a proven track record."

Falling (and climbing) stock

Heading into the Sam F. Davis, Colebrook was confident.

It was sunny in Tampa for this race. Knicks Go’s three workouts in Tampa had been sharp, two being bullets as the fastest on the track at that distance that day.

“He’s the most proven horse in the race,” Colebrook said, “and if he runs back to one of his better races, I think it will take a career-best for somebody to beat him.”

The betting public agreed. Knicks Go’s odds had dropped to 9-to-5 by the time he broke quickly from the No. 3 post.

But in the Sam F. Davis, another horse wanted the lead.

Well Defined, at 7-to-1 odds, and Tampa-based jockey Pablo Morales flew past Knicks Go and Jimenez, opening up a comfortable three-length lead and settling in front without expending much energy to resist a challenge.

While Knicks Go gained a little ground, he never got to Well Defined. No one else did either.

While the convincing victory was only worth 10 Derby points for Well Defined, it legitimately put him on the Derby Trail. For Knicks Go, though he still had 18 points, a fifth-place finish was going to raise serious questions. It meant he had been beaten soundly in a Derby prep race for the second time in a row, counting November’s rainy Kentucky Jockey Club Stakes at Churchill Downs.

Colebrook admitted later that at that point, “I knew that the Derby at that point was probably off the table in some ways."

Meanwhile, there was a suspicion that the best 3-year-old on the premises in Tampa might not have been in the Sam F. Davis.

Nineteen days prior, a horse named Win Win Win had crushed it on the same track, winning by more than seven lengths in the seven-furlong Pasco Stakes. His winning time of 1:20.89 was a track record. His Equibase speed figure came back a salty 113. Well Defined’s Sam F. Davis was a 97.

Win Win Win had won three of his four starts for Maryland-based trainer Michael Trombetta, having shipped to Tampa for the Pasco after running at Laurel Park. The Florida-bred horse fared so well in Tampa that Trombetta kept him there. Without even running a points race yet, Win Win Win was very much on the Derby Trail.

See also:Tacitus rallies up the rail to win the Tampa Bay DerbyTrombetta recommended to the horse's owners, Charlotte Weber's Live Oak Plantation, that they bypass the Sam F. Davis on shortened rest and instead start preparing to stretch out to 1 1/16 miles in the Tampa Bay Derby. It was a gamble, restricting the horse's opportunity in Derby points races from three to two.

“It’s a little bit like March Madness, isn’t it?” Trombetta said. “A lot goes into it. To get to that first Saturday in May, there’s a whole series of things that have to happen particularly well. … If you’re in it, you want to be in it with one that has a shot, and you don’t always have that luxury.”

A veteran trainer with more than 30 years and 1,700 victories, Trombetta’s Kentucky Derby experience, same as O'Connell, was limited to one race.

A high-strung horse named Sweetnorthernsaint won the Illinois Derby for Trombetta to earn a spot in the 2006 Kentucky Derby. His run-up had been so impressive that Sweetnorthernsaint ended up going off as a 5-1 post-time favorite. He finished seventh behind that year’s Derby winner, Barbaro, before going on to finish second in the Preakness.

A year later, Trombetta developed a condition called alopecia areata, which causes the body’s immune system to attack its hair follicles. For Trombetta, that included the loss of his eyebrows and eyelashes in addition to the hair on his head.

“When I saw myself in the mirror, I would startle my own self,” Trombetta told the Maryland Jockey Club in 2017. “I’d been the same person for 40 years. You don’t expect it.”

Emotion, elation and Derby dreams

The celebration around O’Connell’s barn after Well Defined’s victory in the Sam F. Davis was an especially emotional one, and that had little to do with the Derby points.

It had been a heartbreaking few months. O'Connell's mother, Arlene O’Connell, had died Jan. 2 at age 90, almost exactly three months after her father, Joseph O’Connell, a former police officer in Detroit, died in October, five days after his 93rd birthday. O’Connell’s parents had been married 68 years.

“It’s been so tough,” she said, the tears in her eyes, a disarming contrast to a tough-as-nails demeanor while running her racing operation.

Her parents lived in Eagle, Michigan, near Lansing. O’Connell is still a Michigan State fan, though the university once denied her entry into veterinarian school, a disappointment that led her to pursue a career in horse racing.

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“My dad, he wasn't too happy about it to start with. They just figured, 'Well, a few weeks of this and it'll be out of your system,' and it was quite the opposite,” O’Connell said recently in an interview with “Trainer Talk” on the Horse Racing Radio Network. “… I'm proud of (my career) because there isn't anybody in my family or any relatives or anything that had anything to do with the horse business. I just think that it shows perseverance pays. Nothing happens overnight.”

After Well Defined’s victory, it seemed the entire community around Tampa Bay Downs was happy for O’Connell, who had paid her dues and been such an important part of the track's existence for so long.

Her days are long, lasting into the evening if there are races and starting as early as 4 a.m. O’Connell rides her white pony back and forth for hours on the track while horses train.

As she rode off from her barn one morning, the Tampa Bay Derby soon approaching, someone passed her and shouted: “It’s your year, K.O.!”

Just maybe it would be.

Gentry Estes: 502-582-4205; gestes@courierjournal.com; Twitter: @Gentry_Estes. Support strong local journalism by subscribing today: courier-journal.com/gentrye.