Making Money Betting the Favorite in Jessamine Stakes

October 11th, 2021 by J. Keeler Johnson

Fans enjoy turf racing at Keeneland Race Course during its fall 2021 meet. (Coady Photography)

With just over three weeks remaining until the Nov. 5-6 Breeders’ Cup at Del Mar, the Challenge Series is winding down. The final “Win and You’re In” qualifier for the year-end championships will take place on Wednesday at Keeneland, that being the $200,000, Grade 2 JPMorgan Chase Jessamine Stakes.

Held over 1 1/16 miles on turf, the Jessamine serves as a steppingstone toward the Grade 1 Breeders’ Cup Juvenile Fillies Turf, held on Future Stars Friday, Nov. 5. And it’s safe to say the quality of the Jessamine has been stellar. Five of the last six winners have gone on to succeed at the Grade 1 level, including Breeders’ Cup Juvenile Fillies Turf winners Rushing Fall (2017) and Aunt Pearl (2020).

No one will be surprised if the 2021 Jessamine produces a Breeders’ Cup winner as well. A total of 16 fillies (including two on the also-eligible list) have been entered, highlighted by a couple of stakes winners and a large handful of promising maiden winners. It’s difficult to narrow down the contenders, though #3 Turnerloose does loom as a potentially formidable favorite.

Conditioned by Brad Cox (who won the 2020 Jessamine with Aunt Pearl), Turnerloose is undefeated in two starts. The daughter of Grade 1 Kentucky Derby winner Nyquist pressed a slow pace to win her debut racing one mile over the Ellis Park turf course, then delivered an eye-catching performance when stepping up in class for the Aristocrat Juvenile Fillies Stakes at Kentucky Downs. Again racing one mile on turf, Turnerloose tracked the early pace from third place, advanced to challenge halfway through the race, and then powered clear to dominate by five lengths.

With her blend of tactical speed and finishing power, Turnerloose figures to enjoy a favorable trip in the Jessamine, likely staying out of trouble while racing on or near the lead. She’s the most accomplished filly in the field and has drawn well in post three, so what’s not to like? Turnerloose will be tough to catch if she brings her A-game, and we’ll bet the Jessamine accordingly, keying Turnerloose on top of all our tickets.

Turnerloose (Eclipse Sportswire)

The harder question is, which horses should we include for exotic wagers like the exacta and trifecta? #14 Diamond Wow is unbeaten in two starts, wiring her debut over the Gulfstream Park turf course before switching to dirt for a pace-tracking win in the Our Dear Peggy Stakes. But Diamond Wow has never run beyond a sprint distance and is unfortunately marooned in post 14, setting the stage for a tricky trip. Diamond Wow will have to either settle for a wide trip or sprint hard early to try and clear the field, with neither option being particularly appealing.

An alternative to Diamond Wow is #6 Bhoma, hailing from the hot barn of trainer Kenny McPeek. True, the daughter of Bernardini has never run on turf, but her pedigree suggests the surface switch won’t be an issue – Bhoma’s half-sister Mom’s On Strike was good enough to win multiple Grade 3 stakes on grass.

Bhoma has run twice so far, finishing second by a head in her debut before rallying gamely to win a maiden sprint at Churchill Downs. If a hot pace unfolds in the Jessamine, Bhoma figures to be gaining ground late under jockey Brian Hernandez Jr., a 28% winner when teaming up with McPeek over the last two months.

Who else should we include? #8 Queen Judith, a daughter of Belmont Stakes winner Empire Maker, is a must-use contender after rallying fast to win her debut sprinting over the Kentucky Downs turf course. Fellow Kentucky Downs winners #9 Decree of Love, #10 Misthaven, #12 Dressed, and #13 Boxing Day all warrant respect as well. Of particular note is Decree of Love, who finished fast off a slow pace to dominate a one-mile maiden special weight by 2 ¼ lengths.

Then there’s #16 Haughty, shipping in from Belmont Park for two-time Jessamine-winning trainer Chad Brown. The daughter of Empire Maker is unfortunately the second also-eligible and will require a couple of scratches in order to compete. But if Haughty draws in, watch out – she was impressive in her debut racing one mile at Belmont, crossing the wire in front by 3 ¼ lengths before getting disqualified for interfering with a rival at the top of the stretch. A similar performance (minus the interference) should be good enough to put Haughty in the hunt for a top-three finish, though starting from the outside post could be problematic.

#11 Opalina, a 12-length maiden winner racing one mile on turf at Gulfstream Park, is the final runner we’ll consider for our tickets.

Taking all of these opinions together, here are a couple of Jessamine Stakes betting strategies to consider – one based on a $10 budget, and the other based on a $30 budget.

Wagering Strategy on a $10 Budget

$6 to win on #3 Turnerloose

What to say at the betting window: Keeneland, 8^th race, $6 to win on 3

$1 exacta: 3 with 6,8,9,16 ($4)

What to say at the betting window: Keeneland, 8^th race, $1 exacta 3 with 6,8,9,16

Wagering Strategy on a $30 Budget

$12 to win on #3 Turnerloose

What to say at the betting window: Keeneland, 8^th race, $12 to win on 3

$1 exacta: 3 with 6,8,9,16 ($4)

What to say at the betting window: Keeneland, 8^th race, $1 exacta 3 with 6,8,9,16

$0.50 trifecta: 3 with 6,8,9,16 with 6,8,9,10,11,12,13,16 ($14)

What to say at the betting window: Keeneland, 8^th race, $0.50 trifecta 3 with 6,8,9,16 with 6,8,9,10,11,12,13,16