Since first teaming to win a maiden claiming race at Aqueduct in April 1996 during the early part of their careers, trainer Todd Pletcher and jockey John Velazquez have combined to win another 1,865 races together. Among these is a victory in the 2017 Kentucky Derby with Always Dreaming.

Now, 28 years after their first pairing, the duo will attempt to win another Derby, providing yet another achievement in their Hall of Fame careers, when Pletcher gives Velazquez a leg up on Fierceness in the Churchill Downs paddock before the May 4 Kentucky Derby presented by Woodford Reserve. Repole Stable's homebred City of Light colt, the reigning 2-year-old champion and winner of the Grade 1 Curlin Florida Derby presented by Hill 'N' Dale Farms at Xalapa, is likely to be favored, just as Always Dreaming was in 2017.

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Though the sight of Pletcher and Velazquez in the Churchill Downs paddock before the Derby is familiar — they have the most respective Derby starters and rides of any of the Derby's participants — this will mark just the first time since 2018 that they have paired in the Derby. That year, Velazquez piloted Repole Stable's Vino Rosso to a ninth-place finish.

In the years that followed, Pletcher began more often utilizing multiple jockeys, among them Irad Ortiz Jr., Jose Ortiz, and Luis Saez. Velazquez began riding more for Hall of Fame trainer Bob Baffert. For a period of years, Velazquez also shifted his winter base to Southern California, where Baffert stables his horses. Velazquez returned to Florida this winter, citing family issues and, understandably, a desire to stay close to his coveted mount on Fierceness.

Reflecting these shifts, Velazquez has averaged fewer than 20 mounts a year for Pletcher since May 9, 2019, according to Equibase Stats Race Lens statistics. They have teamed for 19 wins over this 85-mount five-year stretch, a tiny fraction of their overall 7,251-ride association. They still won some major races, such as with Malathaat in the 2022 Longines Breeders' Cup Distaff.

For Baffert, Velazquez won the 2020 Kentucky Derby on eventual Horse of the Year Authentic. The next spring, he would also cross the wire first in the 2021 Kentucky Derby on the Baffert-trained Medina Spirit, though the Baffert trainee would later be disqualified.

Coupled with an earlier Derby win in 2011 on the Graham Motion-trained Animal Kingdom, Velazquez officially has three wins in the first leg of the Triple Crown, though his ride on Medina Spirit still lingers in the memories of observers and those that cashed wagering payoffs.

"Phenomenal career, phenomenal consistency," Pletcher said of Velazquez's 34 years in the saddle. I think tactically he is one of the best, if not the best, of all time. He's a great positional rider. He's had success in this particular race and every other race that there is."

Already the third-oldest rider to win the Kentucky Derby at age 48 aboard Authentic, Velazquez could join fellow Hall of Famer Mike Smith (Justify, 2018) in winning the race as a 52-year-old. The late Bill Shoemaker is the oldest jockey to capture the Derby, when at age 54 in 1986 he won aboard Ferdinand.

Fierceness. (Eclipse Sportswire)

"To have this horse with Johnny is special," Repole told BloodHorse earlier this month. "A few years ago, I told Johnny we are going to have another big horse with me, him, and Todd. I didn't know when and he made a joke that I better make it quick, he's getting older."

Opportunity knocked last fall when Pletcher had three horses pointed to the 2023 FanDuel Breeders' Cup Juvenile presented by TAA at Santa Anita Park: Locked, Noted, and Fierceness.

Jose Ortiz, who had ridden Eclipse Thoroughbred Partners and Walmac Farm's Locked to victory in the Grade 1 Claiborne Breeders' Futurity at Keeneland, received the riding assignment on that colt, who would finish third in the Breeders' Cup Juvenile.

Because Irad Ortiz Jr. had ridden both Noted and Fierceness previously, another jockey was needed for the Breeders' Cup. Both horses had question marks, with Noted having more established turf than dirt form and Fierceness being an obvious talent after an initial maiden win that had been followed by a seventh-place finish over a sloppy track in the Grade 1 Champagne Stakes.

"Fierceness had won by (11 lengths) and lost by 20; we didn't know what he would do in the Breeders' Cup. Todd and I decided to put Irad on Noted and put Johnny on Fierceness," Repole said.

Fierceness rolled by 6 1/4 lengths in the Breeders' Cup Juvenile, vaulting him to an Eclipse Award, while Noted ran last.

That left the Velazquez-Pletcher-Repole trio, which previously campaigned Uncle Mo to a 2-year-old championship in 2010, back on top again.

Many observers believe Fierceness is Repole's best hope in the Derby after seven defeats with horses he either raced solely or in partnership. Two other Repole-owned horses, Uncle Mo and Forte, were scratched due to physical reasons as morning-line favorites.

This year, Fierceness ran third in the Grade 3 Holy Bull Stakes on Feb. 3 at Gulfstream Park and won the March 30 Florida Derby by a record-setting 13 1/2 lengths.

Repole said his family and friends, including his NOBULL apparel business partner, retired seven-time Super Bowl-winning quarterback Tom Brady, will be in attendance on Derby day.

But his most valuable athlete at the Derby — John Velazquez — will not be alongside Repole in the stands, but aboard Fierceness on the track. The veteran is the only jockey in this year's Derby to have multiple victories in the race. He has competed in the Derby 25 times including every year since 2007.

"This is what I'm here for. I'm here to ride these kind of races, these kind of horses, and I'm really excited," Velazquez said. -- Bob Ehalt also contributed to this story.