An ultra-competitive field has turned out to contest Friday’s $1.5 million Grade 1 Longines Kentucky Oaks at Churchill Downs. The historic 150^th running of the 1 1/8-mile race for 3-year-old fillies is packed with viable win threats, and a serious case can be made for at least half of the entrants to visit the winner’s circle.

Separating the key contenders isn’t easy, but we’re willing to bet that, in different ways, the third time will be the charm for both #11 Ways and Means (5-1) and her trainer, Chad Brown.

Chad Brown has won the Eclipse Award for Outstanding Trainer on four occasions. He rarely saddles fillies in the Kentucky Oaks, but his two previous entrants both ran well when pegged as the third post-time betting choice in the 5-1 range. In 2016, Lewis Bay finished third at 5-1 odds, while in 2021, Search Results finished one spot better at 5.70-1 odds, ending up second, a neck behind two-time champion Malathaat, in the Oaks.

Chad Brown (Anne M. Eberhardt/BloodHorse)

Perhaps Brown’s third attempt to win the Kentucky Oaks will end with a victory by Ways and Means, whose first two stakes appearances have yielded frustrating runner-up finishes. Ways and Means was the toast of the town after winning her Aug. 6, 2023, debut sprinting at Saratoga by 12 ¾ lengths over a next-out winner. But when Ways and Means stepped up in class for the Grade 1 Spinaway Stakes at Saratoga a month later, everything went wrong. She clipped heels early, then launched a wide rally that fell a half-length short of catching the formidable Brightwork, who ended up winning her third straight stakes.

Ways and Means came out of the Spinaway with a minor injury and didn’t race again until March 30, when she competed around two turns for the first time in the 1 1/16-mile, Grade 2 Gulfstream Park Oaks Presented by FanDuel TV. Stretching out in distance off a long layoff was bound to be difficult, but Ways and Means nearly overcame the odds. After getting bounced around between rivals and squeezed back off the pace, Ways and Means unleashed a sweeping outside bid down the backstretch and briefly took the lead. Unfortunately though, the pacesetters battled back, and Ways and Means got caught up in a prolonged duel while racing wide around the far turn. She understandably grew a little leg-weary down the homestretch and failed by one length to hold off stretch-running two-time stakes winner #12 Power Squeeze (12-1).

Power Squeeze is back again in the Kentucky Oaks, but there are plenty of reasons to believe Ways and Means can turn the tables and finally secure victory in her third graded stakes appearance. Getting in a race off the long layoff figures to improve the fitness of Ways and Means, and fast workouts since the Gulfstream Park Oaks further suggest Ways and Means is poised to move forward. One week out from the Kentucky Oaks, Ways and Means blazed half a mile in :46 1/5 at Churchill Downs, the fastest workout of the morning at that distance. Throw in the fact Ways and Means has already run fast in terms of Beyer Speed Figures and Brisnet Speed ratings, and she’s a compelling choice to win the Kentucky Oaks.

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Assuming her 5-1 morning line odds hold up, Ways and Means is well worth betting to win; even a modest $10 bet will yield $60. But bettors aiming for a bigger score might want to play Ways and Means in the exacta and trifecta with some of the other logical contenders like #5 Thorpedo Anna (5-1), #8 Tarifa (7-2), #13 Just F Y I (9-2), and #14 Leslie’s Rose (4-1).

All of these fillies bring strong credentials to the table. Thorpedo Anna recently ended a four-month layoff with a blowout four-length win in the Grade 2 Fantasy Stakes at Oaklawn Park. Tarifa is 3-for-3 this season, most notably winning the Grade 2 Rachel Alexandra Stakes Presented by Fasig-Tipton and Grade 2 Fair Grounds Oaks Presented by Fasig-Tipton at Fair Grounds. Just F Y I was voted champion 2-year-old filly of 2023 after recording victories in the Grade 1 Netjets Breeders’ Cup Juvenile Fillies and Grade 1 Frizette Stakes, and she started 2024 with a runner-up finish by three lengths against Leslie’s Rose in the Grade 1 Central Bank Ashland Stakes at Keeneland.

But there are reasons to hesitate in playing all these fillies on top. Thorpedo Anna is stepping into the Grade 1 ranks for the first time and hasn’t faced as tough of competition as some of her Kentucky Oaks rivals. The same goes for Tarifa, who suffered her lone defeat from five starts in an allowance optional claimer at Churchill Downs last fall. And Just F Y I and Leslie’s Rose risk wide trips while breaking from far outside post positions.

That’s why we’re going to take a stand playing Ways and Means on top of all our tickets. It’s a risky strategy in such a competitive field, but if we’re correct, we’ll be rewarded with handsome payoffs.     

Wagering Strategy on a $10 Budget

$10 to win on #11 Ways and Means

What to say at the betting window: Churchill Downs, 11th race, $10 to win on 11

Wagering Strategy on a $30 Budget

$18 to win on #11 Ways and Means

What to say at the betting window: Churchill Downs, 11th race, $18 to win on 11

$3 exacta: 11 with 5,8,13,14 ($12)

What to say at the betting window: Churchill Downs, 11th race, $3 exacta 11 with 5,8,13,14

Wagering Strategy on a $50 Budget

$24 to win on #11 Ways and Means

What to say at the betting window: Churchill Downs, 11th race, $24 to win on 11

$5 exacta: 11 with 5,8,13,14 ($20)

What to say at the betting window: Churchill Downs, 11th race, $5 exacta 11 with 5,8,13,14

$0.50 trifecta: 11 with 5,8,13,14 with 5,8,13,14 ($6)

What to say at the betting window: Churchill Downs, 11th race, $0.50 trifecta 11 with 5,8,13,14 with 5,8,13,14

Good luck, and enjoy the race!