May 21, 2005. It’s the third Saturday in May, and locally-trained Scrappy T is in front as the horses round the far turn of the Preakness Stakes. The dark bay gelding, having eased away from the tired pacesetters, now turns his blinkered face toward the home stretch and Preakness glory.

Not far behind, the plucky Afleet Alex – also bearing the hopes of local connections – begins to make his move, catapulting past horses and bearing down like an express train on one final rival to pass. Traffic trouble had hindered his path forward in the Kentucky Derby two weeks ago, but now, there’s plenty of room to run –

Then, suddenly, Scrappy T veers outward, and the next few moments become the stuff of racing legend.

As they headed to the track on that third Saturday in May, trainer W. “Robbie” Bailes turned toward owner Marshall Dowell and remarked, “Marshall, I haven’t told you this yet – but we’re going to win this race today.”

Dowell, who passed away in 2023, was surprised, remembers Bailes. After all, the trainer had never said something like that before any sort of race – let alone the prestigious Preakness Stakes.

But Scrappy T was coming into this contest in fine form. After a pair of third-place finishes in Kentucky Derby preps, his connections decided to forgo the Run for the Roses, and he was entered in the April 30 Withers Stakes at Aqueduct instead. Pressing the pace throughout, the gelding held off all comers to win by a length.

For Scrappy T’s Mid-Atlantic-based team – owner Dowell from Virginia, and Bailes based in Maryland – the Preakness was a natural and exciting next step.

“Everything was falling into place,” the trainer says. “We had been really working with him as far as laying him off the pace – earlier in his career, it was go to the front and go and keep going.

“We had everything – all our ‘I’s dotted and ‘T’s crossed – and we really felt good about it.”

Despite his trainer’s confident words, it would be a tall task ahead for Scrappy T. The field for the Preakness included Giacomo, the improbable 50-1 winner of the Kentucky Derby, plus Derby runner-up Closing Argument and Breeders’ Cup Juvenile champion Wilko.

And then, there was Afleet Alex. A top runner at 2, he’d come back as a 3-year-old with impressive victories at Oaklawn Park, including the G1 Arkansas Derby. After a troubled trip in the Kentucky Derby that saw him settle for third place, beaten by just a length, he would be a force to be reckoned with in this second jewel of the Triple Crown.

“He was training well,” remembers trainer Tim Ritchey. “We were obviously hoping for better trip luck [than the Derby], and with the smaller field, this was probably going to go a little bit better.”

Accordingly, Afleet Alex would go off favored at 3-1, while Scrappy T entered the gate at 13-1. 

During the first stages of the race, Scrappy T sat off a snappy pace set by High Limit and Going Wild, while Afleet Alex settled well behind, in 10^th after a half-mile. The gap wouldn’t last for long, though. Under jockey Jeremy Rose, the bay Northern Afleet colt began to surge past rivals one-by-one.

“He had the fastest turn of foot, I think, of any horse I ever rode,” Rose says. “He really did. He had a punch that I called ‘low running,’ because it felt like he dropped down when I asked him to run – it was a noticeable difference in his drive.”

As Afleet Alex was practically nipping at Scrappy T’s heels, jockey Ramon Dominguez gave his mount some left-handed urging, hoping to keep the gelding focused on the task ahead. (Dominguez told news outlets that day that Scrappy T was caught “off-guard” by the whip.) 

And that’s where the trouble began. Scrappy T darted outward – right in front of Afleet Alex’s forward path. Contact was inevitable.

Afleet Alex stumbled, nearly sending Rose completely out of the saddle. The jockey went from wondering just how many lengths he and his mount would win by, to wondering if they’d win – or even finish – the race at all.

Meanwhile, both trainers watched the moment with bated breath.

Bailes thought Scrappy T was home free, and hadn’t even seen Afleet Alex coming before the incident. “It was a sick feeling,” he remembers. 

Ritchey recalls: “The way [Afleet Alex] was making that move, I’m thinking that it was going to be one of the fastest Preaknesses on record. I mean, he was accelerating. Everything was fine – and then it was, ‘Oh, no.’”

But Afleet Alex did something extraordinary. The bay colt, who’d all but gone down to his knees, righted himself, got back in gear, and rocketed away from Scrappy T – as if nothing at all had gone awry. 

Afleet Alex crossed the wire ahead of his rivals by nearly 5 lengths. Behind him was Scrappy T, who regrouped to hold second by another five lengtths over the Derby winner Giacomo in third.

“I can’t explain it,” says Rose. “I have a picture where his left front is literally behind his right front, and his back legs are spread where his left front should be. That’s how he stayed on his feet. It’s the only time I’ve ever seen something like it in my life.”

WATCH THE AFLEET ALEX-SCRAPPY T PREAKNESS

Twenty years later, the memories of that Saturday at Pimlico live on, especially in the minds of those who experienced it first-hand.

Three weeks after the Preakness, Afleet Alex ran away with the Belmont Stakes as well – his final start, it turned out, as injury cut his career short just months later. It’s hard not to imagine what could have been, had the colt been given the opportunity to build upon an already-incredible career.

“I think, with the way he was starting to mature, that he was going to be a force at four years old,” says Ritchey.

After a successful career at stud, Afleet Alex now enjoys the pensioner life at Gainesway Farm in Kentucky. Rose credits the stallion not just for his own career success but for the legacy Afleet Alex leaves through his incredible performances.

“For him to go against the best three-year-olds in a Triple Crown race and then trip, almost fall, get back up and still win – you’ll never see something like that again,” he says.

Scrappy T, meanwhile, is living out his golden years in Virginia. Following the Preakness, he earned a few other graded stakes placings, then picked up a second career as a riding horse and hunter-jumper. 

Though Bailes says he’s always looking for the next big thing, the gelding and his wild Preakness remains a watershed moment in the trainer’s career. “He’s very special,” the trainer says. “It’s something that I wish every owner and trainer could experience. It’s why I’m still doing what I’m doing, trying to get back and find that horse.”