The Memorial Day holiday consistently offers great racing and this year will be no exception. Santa Anita will offer a trio of important stakes races on Monday to close out the long weekend. Leading the way will be a deep and talented field of nine older turf males in the Grade 1 Shoemaker Mile. Having won five straight starts when running in Southern California, the multiple graded stakes winner Formidable Man will be the one to beat in the one-mile test.
Other big races on Monday include the Grade 1 Gamely Stakes for older turf females and the historic Hollywood Gold Cup on the main track at the classic distance of 1 1/4-miles. In the Gold Cup, Skippylongstocking has the credentials to be a solid favorite, while in the Gamely, Be Your Best will make another trip out West to headline the 9-furlong affair. Without further ado, let's get to my analysis, top picks, and suggested wagers for an excellent day of racing from Santa Anita.
Head over to TwinSpires to wager on our selection of horse racing bets. New users at TwinSpire can claim a $200 Sign-Up Bonus, today!
Live streaming and instant replays
Exclusive rewards programme
Huge variety of bets
$200 Sign-Up Offer
21+ | Terms and conditions apply
The multiple graded stakes winning Irish-bred Be Your Best will look to return to her winning ways on Monday when she headlines a field of nine older turf females in the Grade 1 Gamely Stakes at Santa Anita.
A 5-year-old daughter of Muhaarar, Be Your Best reeled off three consecutive graded stakes wins in New York and Florida before failing last time out in the Grade 1 Jenny Wiley at Keeneland. She caught a turf course softened by rain that afternoon and should appreciate a return to much firmer turf here. Her win in the rich Pegasus World Cup Filly & Mare Turf two starts back was her most important to date.
Three times a stakes winner in ten career starts, Liguria rates serious consideration in the Gamely. In her most recent start the War Front mare rallied strongly to get up for the win in the Grade 2 Buena Vista last month on the Santa Anita turf course. A similar effort here puts her in with a real shot on Monday.
All stakes winners on the turf, Lady Claypoole, No Show Sammy Jo, and Public Assembly are all also capable of earning a Grade 1 victory here. The latter is a lightly raced daughter of More Than Ready and improving with every start. In her two races in Southern California, she looked right at home winning twice at Santa Anita. In a wide-open affair, Public Assembly will be my top pick.
$5 Exacta Box - Public Assembly, Be Your Best, and Liguria = $30
$5 Exacta Box - Public Assembly, Be Your Best, and Lady Claypoole = $30
Visit TwinSpires and Get $200 Sign-Up Bonus
Although he fell short in his attempt to repeat in last month’s Oaklawn Handicap, Skippylongstocking will rate top billing when he stretches out to 10 furlongs for Monday’s Grade 2 Hollywood Gold Cup.
Trained by Saffie Joseph, Jr., Skippylongstocking will look to add his name to an illustrious list of winners of the race which dates back to Seabiscuit scoring in the inaugural edition back in 1938. A consistent graded stakes winner over the past four seasons, the 6-year-old son of Exaggerator has run three times this year, sandwiching third-place efforts in the Pegasus World Cup and Oaklawn Handicap around a win in the Grade 3 Challenger Stakes at Tampa Bay Downs. The class of the field, he has collected over $3.5 million in his career to date.
Chief among his opposition in the Hollywood Gold Cup will be the graded stakes winner Midnight Mammoth. The 6-year-old gelding got good this time last year, which included three straight wins into last July’s Grade 3 Cougar Stakes. After four straight defeats, he may have tipped off a return to his best form last time with a romping win against allowance company last month at Santa Anita.
Another potential danger to the favorite on Monday is the lightly raced Extensive. The 4-year-old City of Light colt has only four lifetime races, but has improved in each start for trainer Michael McCarthy. With two straight sharp wins over the track in March and April, he looks ready to make some noise in his stakes debut. Overall, however, I cannot look past the class of Skippylongstocking. He will be my top pick.
$20 Daily Double Part Wheel - Skippylongstocking with Mi Hermano Ramon and Formidable Man = $40
Claim $200 Sign-Up Offer at TwinSpires
Perfect in his last five starts in Southern California, Formidable Man is the one they will all have to beat among a competitive field of nine older turf males in the Grade 1 Shoemaker Mile on Monday at Santa Anita.
After a failed attempt out East in the rich Pegasus World Cup Turf (G1) two starts back, the Michael McCarthy-trained son of City of Light got right back to business in his last start. Rallying smartly up the rail, Formidable Man earned his second Grade 1 victory in his last three starts when he came home a half-length winner of the Kilroe Mile in early March at Santa Anita. A versatile sort, he should sit off what is expected to be a strong early pace on Monday.
Among the plentiful speed in the Shoemaker Mile are Goliad and Cabo Spirit. The former will be making his first start since fading in the Breeders’ Cup Mile (G1) last November at Del Mar. Before that he won two straight at Kentucky Downs, including the rich Mint Millions Stakes. The latter has won a pair of graded stakes on the Santa Anita turf course, including the Grade 3 American Stakes in his last start.
With plenty of pace a near certainty, Mi Hermano Ramon is one horse who could take advantage. The son of Creative Cause ran some very big efforts late last year and was stuck behind a slow early pace when beaten by Formidable Man last time. Still he got within 1 1/4-lengths at the wire. He also finished well ahead of that rival in the Pegasus World Cup Turf two starts back. Mi Hermano Ramon is my top pick.
$40 Win - Mi Hermano Ramon = $40
Register at TwinSpires for $200 Bonus
After three consecutive prestigious graded stakes races, the holiday card at Santa Anita will crash back down to the ordinary with a maiden race for fillies and mare going 5 1/2-furlongs on the main track.
Approval Rating, a Florida-bred daughter of Ride On Curlin, has knocked on the door in his first two career starts and looks like the one to beat here. After rallying strongly to miss by a half-length in his career debut in April, he came back four weeks later to lose by a neck in his second career start. Assael Espinoza will once again be aboard.
Several in this field finished behind Approval Rating last time, including the beaten favorite Tapatia Leah. The daughter of Stay Thirsty finished in third that day, but did not threaten the top two. After a dull effort in her career debut on grass, she has finished second twice in four tries on the dirt.
There are also a handful of first-time starters in the race that are worth a look against a less than strong field. Calm Down Kimmie has a pair of bullet works at Los Alamitos and could flash speed in her debut. Vronaway is bred to sprint and has a solid string of workouts to her credit. Approval Rating is the one to beat here and is my top pick.
$5 Trifecta Part Wheel - Approval Rating over Tapatia Leah over Calm Down Kimmie, Vronaway, and C Plum Run = $15
$5 Trifecta Part Wheel - Approval Rating over Calm Down Kimmie, Vronaway, and C Plum Run over Tapatia Leah = $15
Responsible Gambling
If you or someone you know needs support or wants to speak with a professional about responsible gambling, seek out the correct resources. Call or text 1-800-GAMBLER to get help, or visit 1800gambler.net for more information. WSN is an advocate for safe gambling practices. Visit our Responsible Gambling Center for more details.
Belmont Stakes 2025 Odds: Journalism and Sovereignty Rematch in the Final Leg of the Triple Crown
2 weeks ago | Brian ZipseBest Horse Racing Bets Today | Churchill Downs
3 weeks ago | Brian ZipseBest Horse Racing Bets Today | Preakness Stakes (Pimlico)
1 month ago | Brian Zipse
We support responsible gambling. Gambling can be addictive, please play responsibly. If you need help, call
1-800-Gambler.
WSN.com is managed by Gentoo Media. Unless declared otherwise, all of the visible content on this site, such
as texts and images, including the brand name and logo, belongs to Innovation Labs Limited (a Gentoo Media
company) - Company Registration Number C44130, VAT ID: MT18874732, @GIG Beach Triq id-Dragunara, St.
Julians, STJ3148, Malta.
Advertising Disclosure: WSN.com contains links to partner websites. When a visitor to our website clicks on
one of these links and makes a purchase at a partner site, World Sports Network is paid a commission.
Copyright © 2025