This is third story in 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 first story here and the second story here

LEXINGTON – As trainer Michael Trombetta walked the winding paths of the Keeneland paddock before the April 6 Blue Grass Stakes, he eyed his horse with a steely poker face.

How was Trombetta doing? “As expected,” he replied.

He hadn’t been sleeping well in the days leading up to the race. It was a road game, so to speak, for the Maryland-based trainer, who’d driven over with his wife two days before. His horse, Win Win Win, had arrived at Keeneland the previous morning.

For a 3-year-old colt with legitimate Kentucky Derby aspirations, it was all down to this. Win Win Win would have to finish at least second of the 14 horses in the Blue Grass Stakes to ensure he’d have enough qualifying points to make the Derby at Churchill Downs.

Highly respected jockey Irad Ortiz Jr. rode Win Win Win — the post-time favorite — to a third-place finish in the March 9 Tampa Bay Derby. While not great, that was acceptable, earning 10 Derby points. He’d need about 30 more to make the 20-horse field for the Kentucky Derby. The Blue Grass was worth 100 points to the winner and 40 to the runner-up. Third place got 20, which was not going to be enough. This would be the final opportunity.

Check out:Trainers fight long odds to break into an exclusive club: the Kentucky Derby

“You just worry about every little last detail,” Trombetta said. “I mean, most of us are the same, because there’s a lot of hopes riding it. You just hope things go the right way. … They’ve got to be a superior runner. Then they’ve got to have a lot of luck on their side and have things fall into place at the right time. The calendar for these races doesn’t move. It’s all got to happen when it’s supposed to happen. If not, you don’t make it.”

Trombetta opted for the Blue Grass at Keeneland over the Wood Memorial at Aqueduct — another race at 1 mile — in part because it allowed him to keep Ortiz as the jockey. He also liked the slightly faster surface at Keeneland.

At 7-to-2 odds, the No. 8 horse Win Win Win was behind only the George Weaver-trained Vekoma (9-5), who’d break from the No. 2 post after finishing third in the March 2 Fountain of Youth Stakes.

Win Win Win had been agitated before his last race, but he calmly walked through Keeneland’s spacious and scenic paddock as Trombetta watched from a distance.

“The pressure increases,” he said. “But at end of the day, they can only do what they can do. We brought him here in good spirits. He’s been training good. So we’ll see what we get.”

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

'He never quit'

In the wake of a next-to-last finish in the March 9 Gotham Stakes, Knicks Go was sent to a doctor for a thorough examination to see what might be bothering him.

Turns out, he was healthy. He just wasn’t running well enough.

By late March, trainer Ben Colebrook was ready to call it, saying Knicks Go should be considered off the Derby Trail.

“I think the Derby is just a bridge too far for me," Colebrook said, "and in the back of my mind, I kind of always thought that. But you don’t want to be negative."

Knicks Go remained an eager celebrity, his personality resounding from his stall. He'll pose for photos, make faces, flap gums and open his mouth as if he's got something to say. A visitor fed him a peppermint, asking out loud if she should hold it palm-up for him, to which Knicks Go nodded his head emphatically in response before nibbling the treat.

On the track, he had proved to be blue-collar, eager to please, hard-working and deceptively athletic with a lot of heart, always trying his best.

“When you watch him train, you like what you see,” Colebrook said. “But when you watch him stand still, he’s not a ‘Wow’ you kind of horse. … The cliche of ticking all the boxes, he wouldn’t be a horse that would tick everybody’s box."

Read this:Cox's Owendale wins Lexington Stakes but falls shy of Kentucky Derby

Knicks Go ended up instead fitting the profile of a successful 2-year-old horse — winning the Grade 1 Breeders’ Futurity and finishing a brave second in the Breeders’ Cup Juvenile — but didn’t carry it over into the first portion of his 3-year-old campaign.

Knicks Go didn’t grow, Colebrook said, from age 2 to 3, a time when other top horses might mature immensely before a Triple Crown run.

“In elementary school, I was the fastest kid in school. But by the time I was a senior in high school, I didn’t get any bigger and didn’t get any faster. It does happen,” Colebrook said. “… From my experience, you need that bump from 2 to 3. You see it every year, a horse gets good as a 2-year-old and it doesn’t translate to a 3-year-old, and that’s kind of why they came up with the points system.”

There would, however, be one final shot for Knicks Go and his Korean ownership team. Colebrook entered him in the April 13 Lexington Stakes at Keeneland, which would be worth 20 Derby points to the winner. If Knicks Go won, his 38-point total would have put him right on the cut line.

He went off at 17-to-1 odds, but back on his home track at Keeneland, he ran much better and raced to the lead. Heading into the final turn, Knicks Go had the lead. On track-side, Colebrook had removed his sunglasses and watched intently as a horse named Owendale passed Knicks Go in the stretch.

"He gave us a thrill," Colebrook said with a smile.

Knicks Go finished fourth. While it wasn't enough for the Kentucky Derby, given his poor recent form, it was an encouraging performance.

"He was fighting. He never quit," said jockey Albin Jimenez, who was back on Knicks Go for the race. "He probably needed a race, because the last two races he was not himself. He looked good."

"It's kind of been a rough go, to be honest," said Colebrook, alongside Jimenez. "But now we're not going to worry about the Derby anymore, and that's good. He's just not that kind of horse. That's fine. Plenty of races for him. Might even try him on the grass or something like that."

Knicks Go's Derby hopes ended on the track. Others were not so fortunate.

See also:Omaha Beach looks like a Kentucky Derby contender at Arkansas Derby

Falling off the Trail

Back in Florida, one of the Kentucky Derby contenders who finished behind Win Win Win in the Tampa Bay Derby was resting and healing for the remainder of his 3-year-old racing campaign.

Well Defined, however, had been forced off the Derby Trail.

He tweaked a long muscle on the left side of his back, likely when he reared up in the paddock before the Tampa Bay Derby. Only a few seconds, as it turned out, to end Derby dreams.

Though it wasn’t a major injury, it was enough that trainer Kathleen O’Connell and Well Defined’s ownership had agreed to rest him through the April prep races, meaning he’d fall short on points for the Kentucky Derby.

“We could have done therapeutics. We could have done this or that,” O’Connell said. “But the only thing I’ve learned over all the years I’ve been in this business is you can’t force it. You can’t make it happen. … I think we’ll see bigger and better things from him, but the most important thing is for him to be healthy.”

It was a discouraging end to Derby hopes for Well Defined’s connections, given that he was a promising 3-year-old gelding who had won the Sam F. Davis Stakes in February. He was considered a favorite for the Tampa Bay Derby, during which he got into a pace duel with the fast-breaking Zenden and ended up tiring and fading to eighth place.

For O’Connell, a veteran trainer who — like Trombetta — has had only one previous Kentucky Derby horse, it underscored the difficulty of the Derby Trail’s small window for 3-year-olds and its points system of qualification that was implemented in 2013.

Check out:What's a furlong? And everything else to know about the Kentucky Derby

“I mean, a lot of people want to fit into that window,” O’Connell said. “But if they want to fit into that window, they should have a fair, fighting chance. The fact that they changed everything — not for the better, I think — for whatever the reason, I just don’t think it’s fair. For years, it went by graded earnings. For years, owners and trainers could do what’s best for the horse as far as plotting a course. …

“You ought to have a choice to get there. You’re going to the big dance. You want to get the horse there the best way possible. But again, it’s not like I’ve got 14 horses that competed in the Derby and I’ve got a lot of Derby experience. I’m just saying this as a person that has run 15,000 horses, because we want what’s best.”

Though he didn't make it with Knicks Go, Colebrook said that he is in favor of the Derby points system.

“I do agree that it kind of forces your hand,” Colebrook said. “But if it’s putting the right horses in the race — and it seems to be, in my opinion — it’s probably the right thing. … Before, a horse like (Knicks Go) that was a Grade 1 winner at 2 got in the Derby, and a horse that ran an awesome second in the Blue Grass wouldn’t get in.”

A Sunshine State captain

The wagering public has continued to like Win Win Win on race days, but in making the 2019 Kentucky Derby, he’d be defying the odds, and not just as one the few 3-year-olds to withstand the road there.

Of the 108 horses drawn into the past five Kentucky Derbys, either in the field or as an also-eligible, 85 of them (78.7%) were bred in Kentucky. New York, with six, was next.

Win Win Win is a Florida-bred, as is Well Defined (Knicks Go is a Maryland-bred).

And while Florida-bred horses have won the Kentucky Derby six times — including 1978 Triple Crown winner Affirmed — it has been 22 years since the most recent, Silver Charm.

In the past four years, only one Florida-bred horse — Firenze Fire in 2018 — has made it to the starting gate of a Kentucky Derby.

“It’s hard to compete with what y’all got up there (in Kentucky). You’ve got the best studs and the best mares,” said Larry King, manager of Florida’s Stonehedge Farm, Well Defined’s breeder and owner. “It’s big to me to even be in the mention with all the big names and the Kentucky-breds.”

Related coverage:Jockeys say whips necessary for their safety and that of the horses

Never sold at an auction, Win Win Win's owner is Live Oak Plantation, an accomplished racing operation in Florida owned by Charlotte Weber, the granddaughter of Campbell’s Soup creator John Dorrance. Live Oak has not had a Kentucky Derby horse since Brilliant Speed, who was seventh in 2011.

Win Win Win, named by Weber, wasn’t necessarily bred by Live Oak to be a Derby hopeful and wasn’t viewed in such a light until January’s impressive Pasco Stakes victory.

“Programs like Mrs. Weber’s, the horses almost have to happen and carry you into the Derby,” said Live Oak general manager Bruce Hill. “Mrs. Weber would love to win the Derby, but she has not just zeroed in on that as being the end-all.”

Hill said Win Win Win has always been different, though. He’s an “alpha” horse, the kind who if he was on a football team, he’d be the captain.

“If he walks in and if everybody’s chattering, he’s the football player that says, ‘Listen up, guys,’ and everybody stops, and they listen,” Hill said. “… Nothing common and cheap about him at all. Some horses are just difficult, and you hold your breath every day because you just don’t know what’s going to happen, and they’re looking for an excuse to do something bad. And this one just feels that good, eats well, travels well, no issues.

“All of this is knock on wood, of course.”

Derby: By a nose

The knock on Win Win Win has been his starting ability. While Well Defined and Knicks Go have each been front-running horses who want the lead quickly, Win Win Win has been routinely slow out of the gate. Even in the record-setting Pasco run, he came from last place.

The thinking was he would have to start better in the Blue Grass, especially against a favorite like Vekoma, who certainly had his game face on.

With the Blue Grass horses gathered and circling Barn 21, Vekoma stopped at one point, suddenly kicking his back feet and breaking the tense prerace stillness with a loud crack when they landed. He did it front of an empty stall No. 8, the one belonging temporarily to Win Win Win. Some gamesmanship, perhaps?

Win Win Win was relaxed in the paddock, and on the track, he started slowly again. He was 13th of the 14 horses, 8 ½ lengths back, after a quarter of a mile. He’d have a crowd to deal with the rest of the way.

Vekoma hung near the lead and then ran in front entering the stretch, sprinting to a 3 ½-length victory.

Win Win Win went wide on the final turn and was at least eight lengths back. He was gaining ground very quickly for Ortiz, though, closing in on tiring horses in front of him as the wire approached. He wasn’t going to catch Vekoma, but he might catch everyone else.

And it was going to be really close.

CJ Investigation:Horse racing is more dangerous than football for concussions. Why US tracks are so far behind on safety

When the horses crossed the finish line, between Trombetta watching at the track and Hill watching at home, neither could be sure between Win Win Win and Signalman.

“It looked like we were second,” Trombetta said, “but it wasn’t a cinch.”

Second meant everything. It meant the Kentucky Derby. Third meant missing it.

Minutes passed before Keeneland posted the order of horses below Vekoma’s No. 2.

“We were holding our breath,” Hill said. “That was a lot of anxiety in that few minutes.”

Then came confirmation.

Second place was Win Win Win.

With 40 Derby points, he was in.

By a nose.

As far as second-place finishes go, “A pretty damn good one,” Trombetta said.

After a dramatic run from the back of the pack, both Win Win Win and Ortiz were covered in dirt when they returned from the gallop-out.

“He was coming,” Ortiz said with a smile. “I like my horse. He came running. I like his style.”

In the know:Horse racing terms to keep you in the know for Kentucky Derby 2019

Despite the irony of a horse named Win Win Win reaching the Kentucky Derby having failed to actually win a points race — finishing third and then second — there were encouraging signs in the Blue Grass for the first Saturday in May.

Two races ago, his ability to run a longer distance was in question, and he’d answered that in surprising fashion. Had the 1 ⅛-mile Blue Grass been longer — as the 1 ¼-mile Kentucky Derby will be — Win Win Win had the momentum to have caught the leader.

“It’s only his second two-turn race today. You’ve got to think about that,” Trombetta said. “For him to do this here with this big field, he’s turning into something I didn’t think he was, this deep closer, two-turn horse. He continues to surprise me. That’s fantastic.”

Ortiz said he liked Win Win Win after the Tampa Bay Derby. And after the Blue Grass, with a Kentucky Derby spot secured, horse racing’s No. 1-ranked jockey to date in 2019, doubled back to make sure Trombetta knew that, too.

“We don’t win the little one, but we’ll go and get the big one,” Ortiz told Trombetta upon exiting for his next mount.

Trombetta smiled and called out in response, “That’s good by me!”

Not so fast

Nine days after the Blue Grass, Ortiz was off Win Win Win and 38-year-old jockey Julian Pimentel was celebrating his first-ever ride in the Kentucky Derby.

Pimentel, based at Laurel Park, had essentially been big-timed on the Derby Trail for Ortiz after riding Win Win Win to victories in three of his first four races. Ortiz, after reaching the Derby with Win Win Win, had then done the same. He jumped on the opportunity to ride trainer Bob Baffert's Improbable instead of Win Win Win, leaving Trombetta in need of a jockey at Churchill Downs.

He went back to Pimentel, who regularly rides for him in Maryland.

"He was just a logical choice, right?" Trombetta said. "He's ridden him four times. He's got three wins and a second, and nobody else has ever been on him other than him and Irad. ... (Pimentel) rode the horse very well. He got along with him, and he didn't have any issues. So he was the next phone call."

Trombetta said he "very much" thought it was a possibility that a highly rated jockey like Ortiz could end up on another horse for the Kentucky Derby. "And it happens often in this business," Trombetta added.

"I thought there was a slight shot it could happen," said Ronnie Gerardo, Pimentel's agent, "and it did happen. ... Julian is a good rider, period. He can ride against anyone. But some owners, they want the top-name riders in the country. It's part of the business. It's nothing personal. You're disappointed, but you can't get upset because you never know what can happen. If we would have got upset and made a bad comment or anything like that, we would have never rode the horse back."

Before the race:Kentucky Derby horses: Who's in and who's out for Churchill Downs

As it turned out, Well Defined's jockey Pablo Morales and Knicks Go's Jimenez, who stayed on for Derby points races, won't make it to the 2019 Kentucky Derby.

But Pimentel, who did not ride Win Win Win's two points races, will get an opportunity — alongside Trombetta and Live Oak — on horse racing's biggest stage.

"He's a friend," Trombetta said of Pimentel. "We've had a long-standing relationship. Sure, I'm very glad for him."

In one case, the process of the Derby Trail had ended up benefiting the little guy.

"It's very rare that you get a good horse and go to a Derby," Gerardo said. "And who knows? The big picture is enormous. If the horse wins, it's the Preakness and on and on. That can open a lot of doors, a lot of opportunities."

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