Monday’s Best Bets and Quick Picks: Churchill’s $54,587 Super High 5 carryover

Handicapper J. Keeler Johnson shares best bets and quick picks for Monday, May 25 at Churchill Downs and Santa Anita, including tickets for Churchill’s $54,587 Super High 5 carryover.

Today’s special offers from TwinSpires include:

• New Players $200 Sign-Up Bonus: Open your TwinSpires.com account using the offer code BET200 to start earning a $200 bonus.
• 15% Odds Boost at Churchill Downs: Receive a 15% boost (up to $25) on your winning single-horse win wagers at Churchill Downs on Monday, May 25.

Today’s TwinSpires tournaments include:

• $76 Churchill Downs Bet and Set Feeder to 6/5 Belmont at Saratoga Bonus Feeder
• $1,000 Churchill Downs KDBC/BCBC Qualifier
• $120 Churchill Downs Feeder to 5/30 Churchill Downs SFBC Qualifier
• $100 Churchill Downs Challenge
• $40 Churchill Downs Challenge
• $64 Belmont at the Big A Feeder to 5/29 Churchill Downs Bonus Feeder
• $40 Belmont at the Big A Challenge
• $46 Mountaineer Bet and Set Feeder to 5/31 Churchill Downs SFBC Qualifier

Best Bets and Quick Picks

Churchill Downs: Race 2: Maiden Special Weight (5 1/2 furlongs on dirt, 1:14 p.m. ET)

#3 Gun for Glory (4-1) is a son of elite sire Gun Runner out of the Tapit mare Easy Tap. This makes Gun for Glory a full-brother to Matt Winn (G3) winner and Travers (G1) runner-up Disarm, as well as to James W. Murphy S. winner Tap Daddy.

Gun for Glory has put together a respectable work tab for Hall of Fame trainer Steve Asmussen and doesn’t appear to be facing the toughest field on Monday, suggesting the chestnut colt has a shot to shine on debut. Let’s bet him to win.

Selections

• #3 Gun for Glory (4-1)
• #7 Hey Tuff Guy (3-1)
• #1 Time for Action (7-2)

Wagers

• $30 to win on #3 Gun for Glory

Churchill Downs: Race 8: Winning Colors (six furlongs on dirt, 4:22 p.m. ET)

#5 Kapoor (3-1), a Godolphin homebred conditioned by Hall of Fame trainer Bill Mott, has led all the way to win four starts in a row by margins ranging from 4 1/4 lengths to 6 1/2 lengths. Last time out, she trounced an $80,000 allowance optional claimer at Keeneland with a career-best 99 Brisnet Speed rating.

Kapoor is progressing in the right direction and may have a shot to upset #7 Usha (7-5), the La Brea (G1) winner who exits a third-place finish in the Derby City Distaff (G1). Let’s play a win bet and an exacta accordingly.

Selections

• #5 Kapoor (3-1)
• #7 Usha (7-5)
• #6 One Magic Philly (6-1)

Wagers

• $15 to win on #5 Kapoor
• $15 Exacta: 5 with 7
  Total: $30

Santa Anita: Race 5: Hollywood Gold Cup (G2, 1 1/4 miles on dirt, 6:00 p.m. ET)

#4 Malarchuk (8-5) earned strong Brisnet Speed ratings of 102 and 106 when finishing first and second in 1 1/8-mile allowance optional claimers at Saratoga last summer.

Malarchuk recently returned from a long layoff with a respectable runner-up effort in the 1 1/8-mile Sunland Park S. He has the pedigree to appreciate stretching out over 1 1/4 miles, so let’s count on Malarchuk to deliver victory in his second start of the season.

#1 Forged Steel (4-1), triumphant in a recent $62,500 allowance optional claimer at Oaklawn Park, can complete the exacta.

Selections

• #4 Malarchuk (8-5)
• #1 Forged Steel (4-1)
• #5 British Isles (3-1)

Wagers

• $24 to win on #4 Malarchuk
• $6 Exacta: 4 with 1
  Total: $30

Carryover Watch

Churchill Downs: Race 1: $54,587 Super High 5 carryover (12:45 p.m. ET)

On Sunday at Churchill Downs, the final three $1 Super High 5s on the card went unsolved. As a result, there’s a triple carryover worth $54,587 up for grabs in Monday’s first Super High 5 offering at Churchill.

The prize pool is up for grabs in Race 1, a $50,000 maiden claimer for three-year-olds and older horses dashing six furlongs on dirt. With 11 horses in the entries, there are 55,440 possible Super High 5 outcomes to analyze.

Wagers

• $1 Super High 5: 9 with 6 with 2,3,7 with 2,3,4,7,10 with 2,3,4,7,10,11 ($48)
• $1 Super High 5: 9 with 2,3,7 with 6 with 2,3,4,7,10 with 2,3,4,7,10,11 ($48)
  Total $96

We rank #9 Dontworryboutnothn (2-1) as the horse to beat. The four-year-old gelding ran twice last year. He debuted with a fourth-place finish in a six-furlong maiden special weight at Keeneland, then switched to turf and ran sixth in a 5 1/2-furlong maiden special weight over the Saratoga turf.

Dontworryaboutnothn has been freshened since July by red-hot trainer Wesley Ward, a 43% winner at Churchill Downs this meet. Ward wins at a 23% rate with horses returning from layoffs of 90 days or more, and at a 24% rate with horses switching from maiden special weight to maiden claiming company, so dropping in class for his 2026 debut should make Dontworryboutnothn tough to beat.

We’ll key Dontworryboutnothn on top in the Super High 5. Underneath, any number of horses could factor for a top-five finish. We’ll emphasize #6 Ghost Protocol (6-1). He’s only run once, finishing second by one length in a five-furlong maiden special weight on turf at Gulfstream Park. His pedigree suggests he’ll handle the switch to dirt, and take note, trainer Kent Sweezey wins at a sharp 25% rate with horses dropping from maiden special weight into maiden claiming company.

For the remaining slots, we’ll use many horses, particularly second-time starter, #2 My Lucky Penny (15-1), the improving #3 Join (12-1), and the unraced #7 Krewezin (12-1).

Good luck!