Hollywood Gold Cup Predictions, Picks Betting Odds (Santa Anita Park)


Fresh off an impressive front-running score in the Grade 2 Californian on April 30, Stilleto Boy headlines a compact field of five set for the 84th running of the Grade 1 Hollywood Gold Cup on Monday at Santa Anita.

The 4-year-old Shackleford son was third in the Santa Anita Handicap and Pegasus World Cup earlier in the year. He will now be trying for his sixth Grade 1 win.

Chief will be Royal Ship, who is his closest rival in the 1 1/4-mile Gold Cup. He was second, only one point ahead of Royal Ship in the last edition. This is his first win since the Californian seven weeks back.

Trained by Richard Mandella and a 6-year-old Brazilian Import, Defunded was the winner of the Santa Anita’s ungraded John Shear mile at Santa Anita. It was his first race for nearly eight months.

Second, in a pair graded stakes last Summer, Defunded should also be given a lot of attention during the holiday feature. After a long layoff, Defunded was an easy winner in his first race.

Previously trained by Bob Baffert in the Dialed In mare, the four-year-old Dialed in horse won an allowance race at Santa Anita with ease in his third start under Sean McCarthy.

Hollywood Gold Cup Predictions & Race Analysis

Stilleto Boy Ridden by J. J. Hernandez for the first-time, the gelded Son of Shackleford took the lead in the nine-furlong Californian. He put in a strong performance over Santa Anita’s main track. As he attempts an additional furlong, I expect him to use the same strategies on Monday.

In fact, his biggest victories, the Californian, and the Iowa Derby last season, were both won by him using his speed early in life to win. He put in a few good performances, even though he was a bit off pace. However, the rider change might have been the right thing.

The distance is a concern, but he has battle-tested his horse and proved to be very agile. He is the fastest horse in the race, and he’s the class. He is our top choice.

Royal Ship This son of Midshipman was in the running to win last year’s race. He led for a long stretch but couldn’t hold Country Grammer off late in his best performance.

He was disappointed in two of the races following last year, but had a good win last month. Mike Smith will be riding him again. I expect him not to let Stilleto Boy get his way. That could be a tough task in the 10-furlong Gold Cup.

His quick return win gave him hope that he could run another major race this year. However, I like him only third-best.


Trained by Sean McCarthy, this Dialed In gelding made solid headway in graded stakes races as a lightly raced 3-year-old last season. He finished second in both Los Alamitos Derby and the Affirmed after finishing fourth in Grade 1 Santa Anita Derby.

He was granted a break from the graded stakes competition and won an allowance win to end his season. After a layoff, he returned to winning well in his first year.

With Stilleto Boy being the fastest and most likely to chase the Royal Ship, this horse could be in good position early on behind the favorites. Although it will be difficult to beat the favourite, I think he is the most likely to win the race.

There Goes Harvard

This consistent son of Will Take Care will face his toughest test yet Monday. Either first or second in every race that he has finished in the last eight, he comes into the race off an impressive victory in a turf allowance race 16 days ago.

Like Royal Ship, Defunded and others, he seems to be in good shape and has enough tactical speed to keep in touch with his horses early. He is not yet able to do enough on dirt for me to be confident he will win the Hollywood Gold Cup.


A grade 2 winner as a juvenile, this son of Union Rags has been unable to fulfill the potential he showed early on. He will be an outstanding longshot for this Grade 1 event, having only won one allowance in his last two years.

Given his recent form, beaten a combined 41 lengths in three consecutive graded stakes, it’s difficult to imagine him suddenly popping up here with a big effort. I don’t think he is for me.

How to Watch the Hollywood Gold Cup

Hollywood Gold Cup Race Information What Hollywood Gold Cup (Grade 1) Location Santa Anita Park Time Monday, May 30 — 5: 30 pm Eastern time How to Watch TVG Purse $400,000

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