In the 18 hours that followed Stilleto Boy’s upset win in Saturday’s Grade 1 Santa Anita Handicap, trainer Ed Moger’s itinerary included a celebratory meal with friends and family at a famous steakhouse near Santa Anita, reading a flurry of congratulatory text messages, and a predawn drive on Sunday to Golden Gate Fields towing a trailer with three horses. Sleep was low on the list of priorities. “I didn’t sleep much,” Moger said on Sunday morning. “I usually sleep like a log.” Stilleto Boy’s longshot win in the Big Cap was a career achievement for Moger, and his brother, Steve, who owns the 5-year-old. While the race may have a diminished role in the handicap division because of more lucrative opportunities in other countries or states, the $500,000 Big Cap still carries massive prestige for lifelong Californians. :: Get ready for Santa Anita racing with DRF Past Performances, Picks, and Clocker Reports.  The Big Cap was first run in 1935, a few months after Santa Anita opened. It was once a destination on the wintertime stakes schedule for leading older horses, but is overshadowed at this time of year by the $3 million Pegasus World Cup at Gulfstream Park in January, the $20 million Saudi Cup in Saudi Arabia in February, and the $12 million Dubai World Cup on March 25. The Big Cap is no longer the richest annual race in California, a distinction that goes to the $1 million Pacific Classic at Del Mar in late summer. That did not matter to the Mogers as dusk fell at Santa Anita late Saturday afternoon. “I told my brother, ‘You won the freaking Big Cap,' ” Ed Moger said. “To me, the Santa Anita Handicap is a more famous race than the Pacific Classic. The purse is bigger in the Pacific Classic, but I’m fine with it.” Stilleto Boy gave Ed Moger his second career win in a Grade 1, preceded by Stormy Lucy’s victory in the Matriarch Stakes for fillies and mares on turf at Del Mar in 2015. Stilleto Boy, bought for $420,000 at a horses in-training sale in July 2021, was third in the Pegasus World Cup on Jan. 28, finishing 5 3/4 lengths behind Art Collector. Stilleto Boy set the pace and faded from contention in the final furlong of that race at 1 1/8 miles. In the Big Cap at 1 1/4 miles, Stilleto Boy stalked the pace, and closed with a determined run in the last furlong to win by a neck over Proxy. The result was decided in the final strides, and was so tight that Moger was content with a placing while watching the stretch run. “I was hoping he would run second,” Moger said. “Then the wire came at the right time.” Stilleto Boy was ridden by Hall of Famer Kent Desormeaux, who returned to riding in November after missing nearly 10 months of racing because of personal issues last year related to alcoholism. Desormeaux, who turned 53 on Feb. 27, has won the Big Cap three times in his career, including in 1992 on the popular gelding Best Pal. Saturday’s win was Desormeaux’s first victory in a Grade 1 since Beyond Brilliant in the Hollywood Derby at Del Mar in November 2021, and first stakes win at Santa Anita this year. “He’s a great rider and always has been,” Moger said. Moger praised Desormeaux’s tactics to urge Stilleto Boy away from the gate, and then track pacesetter Defunded. With a quarter-mile remaining, Stilleto Boy was fourth by two lengths and steadily made progress to reach the front. Stilleto Boy, a winner of 4 of 21 starts, has earned $1,711,675. Stilleto Boy has earned $1,362,000 since he was purchased. The Mogers have set the Grade 2 Oaklawn Handicap on April 22 as a goal for Stilleto Boy. The $1 million Oaklawn Handicap is run at 1 1/8 miles. The longer-term goal is the Pacific Classic on Labor Day weekend and the Breeders’ Cup Classic at Santa Anita on Nov. 4. “We’re going to try to space the races so that he might be ready for us,” Moger said. :: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.