The Hollywood Gold Cup is the race movie stars attended and the race won by a movie star – Seabiscuit, who won the inaugural Gold Cup in 1938.

Stilleto Boy-H Gold Cup
Stilleto Boy won the Grade 2 Californian on the lead. The question is: can he win the Grade 1 Hollywood Gold Cup in the same fashion? (Image: Benoit Photo)

It’s the race won by Triple Crown champions Affirmed and Citation, who retired after winning the 1951 edition. That race made him a millionaire.

And from 1938 to 2013, it was Hollywood Park’s flagship race. From 2014-2019, it went by the Gold Cup at Santa Anita, its new home after Hollywood Park closed in 2013. Then, in 2020, Santa Anita officials changed the name back to reflect the race’s storied past.

Today, it’s one of the three West Coast marquee races for older horses. The Grade 1, 1 ¼-mile Hollywood Gold Cup is the sandwich between March’s Santa Anita Handicap and August’s Pacific Classic at Del Mar. It’s a race every West Coast trainer would take on the resume – especially this edition.

Win a Gold Cup, join Seabiscuit, Affirmed, Citation

That’s because Monday’s Hollywood Gold Cup, the headliner on Santa Anita’s 10-race Memorial Day card, features five horses without a Grade 1 win. That a race with this pedigree has a five-horse field of Grade 1 maidens is mind-boggling when you think about the legends on this race’s winner’s roll. Aside from Affirmed, Citation and Seabiscuit, you’ve got three-time winners Native Diver and Lava Man. You’ve got two-time winner Game On Dude.

You’ve got Kentucky Derby winners Real Quiet, Ferdinand and Swaps. And you’ve got mainstays like Cigar, Ack Ack, Skip Away, Accelerate and last year’s winner, Country Grammer.

Rarefied air, to be sure. So who are the likely candidates to breathe that air? Start with Stilleto Boy, the 7/5 second choice. He rides in off a scintillating 2 ¼-length victory in the Grade 2 Californian, one that produced a 117 Equibase Speed Figure and a career-best 108 Beyer Speed Figure. That came after he cut back to 1 1/8 miles after a third in the 10-furlong Santa Anita Handicap.

Did Stilleto Boy turn a corner here?

In turn, that was Stilleto Boy’s third consecutive third-place finish, coming after a third in the Grade 1 Pegasus World Cup Invitational (at 1 1/8 miles) and the Grade 1 Malibu (at seven furlongs). But that Californian may be a watershed race for the 4-year-old gelding. He led from gate to wire, holding off favored Express Train in deep stretch for his first graded stakes score in 15 career races and seven graded stakes tries.

Speaking of Express Train, last year’s third-place finisher in this race isn’t here. Trainer John Shirreffs is giving the three-time 2022 stakes winner a freshening before turning him loose at Del Mar this summer.

The questions surrounding Stilleto Boy are: can he win at 10 furlongs? And can he win a race like this setting the pace, instead of stalking? He broke his maiden from the front. He won the Iowa Derby from the front. Meanwhile, Stilleto Boy manages to find the board — but not win — against Grade 1 competition as a stalker. See his second to Medina Spirit at 54/1 in the Grade 1 Awesome Again last fall,

“We’re not going to send him or anything. We’ll get him out there, get him into the race and play it by ear,” trainer Ed Moger Jr. told Santa Anita’s Ed Golden. “In the Californian, I told (jockey) Juan (Hernandez) to kind of hustle him into the race and then just play it by ear. He got a pretty easy lead and that’s how it was. But I think his best races have been when he’s halfway close to the pace.”

Royal Ship sails into Gold Cup with form

The other horse who figures to be in the mix is the 2021 Californian winner and your 6/5 favorite, Royal Ship. In last year’s Hollywood Gold Cup, he finished a head behind winner Country Grammer, which seemed to portend a great summer.

Not quite. The Brazilian gelding finished third in the Grade 2 San Diego Handicap, then finished a distant seventh in the 10-furlong Pacific Classic as the 2.70/1 second choice. That prompted trainer Richard Mandella to dock Royal Ship for the next 7 ½ months.

Mandella brought him back for the Listed John Shear Mile, then watched Royal Ship bomb the field in that April race by five lengths as the 1.40/1 favorite.

Grade 1 Hollywood Gold Cup/Santa Anita Park

Morning Line (Jockey/Trainer)

  1. There Goes Harvard, 8/1 (Irad Ortiz Jr./Michael McCarthy)
  2. Royal Ship, 6/5 (Mike Smith/Richard Mandella)
  3. Spielberg, 20/1 (Flavien Prat/Sean McCarthy)
  4. Defunded, 3/1 (Abel Cedillo/Sean McCarthy)
  5. Stilleto Boy, 7/5 (Juan Hernandez/Ed Moger Jr.)

Like his rivals, Royal Ship hasn’t run 1 ¼ miles in his career. But those scared off by the fact Stilleto Boy seems to be in between running styles and hasn’t won back-to-back races in his career have a good alternative.