In the waning weeks of 1999, Laffit Pincay, Jr. was chasing destiny. With each day, he was one step closer, and everybody knew it was coming. On December 10, Pincay finally reached the top of the mountain, becoming the world's winningest jockey when he overtook Bill Shoemaker at Hollywood Park for win number 8,834. The moment was a tribute to both men. For Pincay, the native of Panama who found the American Dream, it displayed his gifted riding ability and commitment to fitness, both of which had paid off many times in more than thirty years in the saddle.

For Shoemaker, it highlighted his longevity and dominance. He seized the record in 1970, and did not relinquish it for nearly thirty years. Outside of Pincay, no one had even approached Shoemaker in career wins during that time (only Russell Baze has done so since then).

Pincay and Shoemaker. They were competitors, and they were friends. They were also two of the all-time greats, and no other jockey has dominated California racing like either of them did.

More than two years later, in the summer of 2002, Pincay was back at Hollywood Park. As Yogi Berra would say, it was deja vu all over again. Pincay was on the cusp of yet another record, and he found himself again equal with none other than Shoemaker.

During the previous July, Pincay won his eighth Hollywood Gold Cup aboard Aptitude after the disqualification of Futural. It had been fourteen years since Shoemaker last won the race, piloting Ferdinand to the victory. The fact they were tied again showed their stature in Southern California racing, the link they have shared for years as the best riders in the Golden State. They stood tall over every jockey to ever be part of a colony in the area, their multiple wins in races like the Santa Anita Handicap and Hollywood Gold Cup gave a glimpse of their riding prowess. Another sign of their dominance, both individually and collectively, came in the form of riding titles. The duo combined for dozens of those honors at each of the major Southern California racetracks, putting them on a higher level than even some fellow Hall of Fame jockeys.

Going into the 63rd edition of the Gold Cup, Pincay was one of the big stories as he set out to further his legend. If he won the Gold Cup, it would be aboard Sky Jack, winner of the Grade II Mervyn LeRoy Handicap earlier in the meet. Five more horses were entered, and the favorite come post time was Milwaukee Brew, who happened to be racing for history as well. The son of Wild Again was the reigning champion of the Santa Anita Handicap. Very few horses had ever won both the Big 'Cap and the Gold Cup in the same year since both races debuted in the 1930s, and that gave Milwaukee Brew the chance to join an elite list at the Track of the Lakes and Flowers.

Whether it came from Pincay or Milwaukee Brew, everyone on track at Hollywood Park on July 14, 2002 were in line to see history made right before their eyes.

The public liked Milwaukee Brew's chances to win, making him the 7-5 favorite. Sky Jack was not far behind, though. The tote board had him listed as the second choice at just under 2-1. The bettors seemed to believe something special was in store after 1 1/4 miles. They just were not certain which moment they would see. The closeness in the betting only heightened the anticipation.

After the gates opened, Sky Jack moved steadily up to the front, grabbing the lead just before the first visit to the wire. To his left were Dig for It, Momentum, and Macaneo. Milwaukee Brew settled in fifth, moving leisurely but with a look of confidence, and racing near the inside was Dollar Bill.

Sky Jack had company going around the clubhouse turn, with Macaneo staying right by. Momentum and Dig for It were close to the front duo, tracking them closely as they began the backstretch run. Dollar Bill ran by himself in fifth. Meanwhile, Milwaukee Brew was already down several lengths, a familiar spot for him as the lead was for Sky Jack. It was like the Big 'Cap a couple months earlier. Sky Jack was in early contention before fading, while Milwaukee Brew rallied to get the win. Whether a repeat of that was seen in the Gold Cup was yet to be determined.

The pace was decent for the 1 1/4 mile distance after a half-mile. Sky Jack produced fractions of 23.41 and 46.94. Not far from the second turn, Pincay sat still on Sky Jack. He had been in this position countless times before, contending for a stakes win and also having history on the line. He and Sky Jack seemed relaxed, and there was no questioning the focus of the legendary rider. He rode to win.

Momentum took up second before leaving the backstretch, relegating Macaneo to third. Dig for It and Dollar Bill completed the pack racing closely together, separated by a few lengths. Milwaukee Brew was still far back as Sky Jack moved around the turn, already being asked for more by Pincay. Momentum and Garrett Gomez made a race of it, challenging as the top of the stretch loomed. Milwaukee Brew and Kent Desormeaux unleashed their rally as the top two battled, ready to claim the Gold Cup. They went to the extreme outside turning for home, overtaking Dollar Bill and Dig for It.

Ahead of them, the gray Sky Jack and the brown Momentum engaged. Pincay and Gomez, two of the sport's fiercest riders, did the same. Sky Jack was on the inside, Momentum next to him on the right. Each horse raced gallantly, moving side by side. Momentum seemed to have the lead for a fleeting moment, but Sky Jack was not backing down. Milwaukee Brew tried to catch them, but a win was not coming his way. With the crowd cheering the leaders on, Sky Jack put his head and neck out in front. But Momentum would not give up. Just before the wire, he made one last surge, coming to the wire with Sky Jack in a photo finish that stunned the crowd.

Neither Pincay or Gomez celebrated. The margin was too close. History was going to be decided by a picture.

A couple of minutes later, everyone saw the tote board flash the number of the winning horse: 5. That was Sky Jack, who captured his first and only Gold Cup and gave Pincay his record ninth trophy in the race. The crowd expressed its approval when Sky Jack won, and many joined him and Pincay in the winners' circle. After the race, the jockey was humble, grateful for the win and for the career he had compiled.

Everyone who saw the stretch battle of the 2002 Hollywood Gold Cup saw vintage Laffit Pincay, Jr. One of racing's greatest money riders, he had been involved in a plethora of stretch battles after more than three decades at the races. Although a senior member of the jockey colony, Pincay was tenacious as ever, still wanting to win. That dedication brought him numerous accolades, wins, and records, and now he had another of the latter on his resume.