Monday’s Best Bets and Quick Picks: Pimlico’s $384,474 Pick 6 mandatory payout

May 27th, 2024

Handicapper J. Keeler Johnson shares best bets and quick picks for Monday, May 27 at Aqueduct and Churchill Downs, along with analysis of Pimlico’s mandatory-payout $384,474 Pick 6 carryover.

Today’s special offers from TwinSpires include:

  • Assiniboia Downs 15% Win Bonus: Receive a 15% bonus (up to $25 per day) on winning single-horse win bets every Monday and Tuesday at Assiniboia Downs from May 20-28.
  • Memorial Day Odds Boost: Receive a 15% bonus (up to $25 per day) on winning single-horse win bets on Monday at Aqueduct, Churchill Downs, and Santa Anita.

Best Bets and Quick Picks

Aqueduct: Race 1: Maiden Special Weight (5 1/2 furlongs, 1:05 p.m. ET)

#2 War Tax (5-1) is the morning line fourth choice in a six-horse field, perhaps because trainer Carlos Martin wins at a modest 9% rate with first-time starters. But there are reasons to believe War Tax can outrun expectations.

For starters, check out his work tab. On May 9, he breezed a bullet half-mile from the Belmont Park training track starting gate in :46. He followed up that blazing exercise with another bullet half-mile from the starting gate in :47 on May 18.

Also encouraging is the fact War Tax is a son of Outwork, who sires a sharp 16% winners from first-time starters. For these reasons, we’ll bet War Tax to win and single him to start a cold double wager.


  • #2 War Tax (5-1)
  • #4 Authentic Kingdom (7-5)
  • #5 My Mitole (4-1)


  • $20 to win on #2 War Tax
  • $10 Exacta: 2 with 4
    Total: $30

Aqueduct: Race 2: Wonder Again (G2, 1 1/8 miles on turf, 1:34 p.m. ET)

#6 Sweet Rebecca (2-1) has unleashed terrific homestretch acceleration to win her first two starts in convincing fashion. In her debut racing one mile against maiden special weight company at Gulfstream Park, she sprinted her final quarter-mile in approximately :22.36 to close from six lengths back and win by one length. Then in the one-mile Memories of Silver S. at Aqueduct, she stayed closer to the early tempo before running her final quarter in :22.48 to prevail by 1 1/2 lengths.

Sweet Rebecca looks like a possible Grade 1 winner in the making, so we’ll count on her to conquer a small field in her graded stakes debut. In addition to a large win bet, we’ll single Sweet Rebecca to conclude our double wager.


  • #6 Sweet Rebecca (2-1)
  • #1 Segesta (3-1)
  • #5 Curlin’s Girl (9-2)


  • $30 to win on #6 Sweet Rebecca

Churchill Downs: Race 9: Maiden Special Weight (seven furlongs, 4:55 p.m. ET)

Since 2022, trainer Eddie Kenneally has compiled a sharp 2-for-8 (25%) record debuting three-year-olds in dirt sprints at Churchill Downs. This suggests Kenneally’s #12 He’s a Joker (20-1) could be live in his first start.

A son of multiple Grade 1 winner Practical Joke (who sires a lofty 16% winners from first-time starters), He’s a Joker has put together a sharp work tab, including a bullet five furlongs in :59 4/5 at Churchill Downs. There are enough positives in He’s a Joker’s corner to make him worthy of a win bet at anything near his 20-1 morning line odds.


  • #12 He’s a Joker (20-1)
  • #1 World Record (3-1)
  • #11 Term (7-2)


  • $20 to win on #12 He’s a Joker

Carryover Watch

Pimlico: Race 4: $384,474 Pick 6 mandatory payout (1:58 p.m. ET)

Less than 10 days after hosting the Preakness (G1), Pimlico is set for another big day of racing. The Memorial Day card is highlighted by the mandatory payout of a $384,474 Pick 6 carryover.

The 20-cent wager is normally a jackpot-style bet that pays out its carryover only if a unique winning ticket is sold. But on Monday, all bettors who select the highest number of winners (presumably six) will split the carryover equally.

The sequence is packed with large fields, and uncovering the winning combination won’t be easy. The first leg (Race 4) and the last leg (Race 9) in particular look challenging, as they’re maiden races with many viable contenders.

To aid your handicapping, we’ll examine both races:

Race 4: Maiden Special Weight (4 1/2 furlongs)

Nine juveniles, seven of them first-time starters, are set to face the starter. Some bettors will be drawn to #6 Rapido Rosa (3-1), who posted a 75 Brisnet Speed rating (only one point below the par winning number for Race 4’s conditions) when finishing a pacesetting third in her debut over this distance and class level at Laurel Park. But Rapido Rosa is trained by Jose Corrales, who wins at a modest 6% rate with second-time starters, so Rapido Rosa doesn’t appear unbeatable.

We recommend backing up Rapido Rosa with a pair of first-time starters. #7 Up in Flames (5-2) is the slight morning line favorite for trainer John Salzman Jr., who wins at a 21% rate with first-time starters. Up in Flames breezed a bullet three furlongs in :36 4/5 last Tuesday and is a logical threat, though we might slightly prefer the chances of #5 Buoyant (7-2). A son of juvenile Grade 1 winner Union Rags, Buoyant has put together an encouraging work tab for trainer Brittany Russell, who strikes at a 22% rate with first-time starters.

Race 9: $30,000 Maiden Claiming (one mile on turf)

This is a beastly difficult race to handicap. Nine of the 11 entrants are dropping in class, many are switching surfaces, and a few have yet to race on turf. You can find a reason (or reasons) to project improvement for plenty of horses, and it wouldn’t be surprising see a double-digit longshot take home top honors.

So where do we begin in sorting out the contenders? Perhaps by analyzing the potential pace scenario. The field is stuffed with deep closers, so a pedestrian pace seems likely. This could lend an advantage to #11 No Surrender (4-1), the only obvious speed horse in the field.

No Surrender has set or pressed the pace in three of his last five starts, all on dirt at Aqueduct. Those were $20,000 claimers, but No Surrender hit the board in all of them. And while No Surrender faltered in his lone turf try racing one mile at Laurel Park last fall, finishing eighth, that was a tougher $45,000-$36,000 maiden claimer in which No Surrender gained a lot of ground from off the pace to finish only three lengths behind the winner.

No Surrender’s pedigree is geared reasonably well toward success on turf, so returning to grass for a paceless $30,000 maiden claimer could make him dangerous on the front end. We’ll use others too—like the reasonably tactical #9 States United (7-2) and the class-dropping #3 Rock Bullet (5-1)—but No Surrender is our top pick to spring a mild surprise.

Good luck!