One of the most competitive Road to the Kentucky Derby Presented by Woodford Reserve qualifiers so far this year is taking place at Turfway Park on Saturday, March 23: the $700,000, Grade 3 Jeff Ruby Steaks, held at a distance of 1 1/8 miles over Turfway’s all-weather Tapeta Footings track.

Several factors make the Jeff Ruby challenging to handicap. The first is the field size – the race has drawn an overflow group of 14 horses, including two also-eligible entrants who will only compete if there are scratches from the main body of the field. One of the also-eligibles, #13 Circle P (30-1), is guaranteed to draw in since #5 Agate Road (4-1) is expected to scratch in favor of Saturday’s Grade 2 Twinspires.com Louisiana Derby at Fair Grounds.

Of the remaining 13 entrants, only three have ever competed over an all-weather track, so predicting which of the other 10 will appreciate it comes down to educated guesswork. Throw in the fact the top contenders appear evenly matched, and deciphering the Jeff Ruby is anything but easy.

That’s why we’re going to take a scattershot approach, emphasizing the top Jeff Ruby contenders in the exacta (and, depending on your budget, the trifecta) while mixing in a few others. Thanks to the large and competitive field, the return on investment should be solid even if a fairly predictable outcome unfolds.

We’ll start with #10 Endlessly (5-2), the morning-line favorite after sandwiching victories in the Grade 3 Del Mar Juvenile Turf Stakes, Grade 3 Zuma Beach Stakes, and El Camino Real Derby around an eighth-place finish (beaten by only 3 ½ lengths) in the Grade 1 Prevagen Breeders’ Cup Juvenile Turf.

Endlessly competed exclusively on turf last year, compiling a 3-for-4 record, but he successfully switched to Tapeta when kicking off 2024 in the El Camino Real Derby, launching a big finish from off the pace to prevail by 1 ¼ lengths. Stretch runners tend to perform well racing one mile or farther at Turfway Park, cementing Endlessly as a key win threat in his first start outside of California.

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#4 Noted (10-1) is another strong contender. Although he’s yet to race over an all-weather track, Noted has won stakes on both turf and dirt. On turf, he rallied strongly to win the Pulpit Stakes at Gulfstream Park and finish second in the Grade 2 Castle & Key Bourbon Stakes at Keeneland, in addition to breaking his maiden at Saratoga. On dirt, he won the one-mile Sapling Stakes at Monmouth Park last year over Dornoch and Frankie’s Empire. Dornoch has since won the Grade 2 Remsen Stakes and Grade 2 Coolmore Fountain of Youth Stakes on the Road to the Kentucky Derby, while Frankie’s Empire has won the Swale Stakes and finished third in the Fountain of Youth.

Given that Noted has beaten quality competition on both dirt and turf, there’s no reason to think he won’t handle Tapeta just fine. It helps that he’s a son of Cairo Prince, whose progeny have thrived over a wide variety of surfaces and distances.

If we focus on betting Endlessly and Noted on top of our tickets, then the rest of the Jeff Ruby field falls into place a bit easier. We’ll round out our tickets with three horses: #6 Northern Flame (5-1), #7 Woodcourt (6-1), and #9 Seize the Grey (8-1).

Northern Flame has already hit the board in a couple of Road to the Kentucky Derby qualifiers, including when third in the Grade 2 Rebel Stakes at Oaklawn Park last month. Although he’s yet to race on anything but dirt, it’s important to note Northern Flame is a son of Flameaway, a graded stakes winner on dirt and turf whose foals include Julia’s Dream (winner of the Gowell Stakes at Turfway) and Blue Eyed George (placed in the Leonatus Stakes and John Battaglia Memorial Stakes at Turfway). Northern Flame’s pedigree offers potential for success on an all-weather surface.

Woodcourt is already proven over Turfway’s Tapeta Footings track, having pounced from a few lengths off the pace to win a $50,000 allowance optional claimer racing one mile at Turfway by three lengths. He subsequently switched to dirt at Oaklawn, where he won a $100,000 allowance optional claimer before finishing fourth (only one length behind Northern Flame) in the Rebel. A top-three finish may be within reach while returning to Turfway.

As for Seize the Grey, he showed flashes of potential last year, but elevated his game to a new level when ending a four-month layoff in a $100,000 allowance optional claimer at Oaklawn last month. Racing 1 1/16 miles, Seize the Grey rated about two lengths off the early pace before finishing nicely down the homestretch to prevail by one length. The son of champion Arrogate is bred to improve with distance and maturity, so he’s eligible to step forward again while stretching out over 1 1/16 miles for the Jeff Ruby.

Wagering Strategy on a $12 Budget

$3 exacta box: 4,10 ($6)

What to say at the betting window: Turfway Park, 12^th race, $3 exacta box, 4,10

$1 exacta: 4,10 with 6,7,9 ($6)

What to say at the betting window: Turfway Park, 12^thrace, $1 exacta 4,10 with 6,7,9

Wagering Strategy on a $36 Budget

$6 exacta box: 4,10 ($12)

What to say at the betting window: Turfway Park, 12^th race, $6 exacta box, 4,10

$2 exacta: 4,10 with 6,7,9 ($12)

What to say at the betting window: Turfway Park, 12^th race, $2 exacta 4,10 with 6,7,9

$1 trifecta: 4,10 with 4,10 with 6,7,9 ($6)

What to say at the betting window: Turfway Park, 12^th race, $1 trifecta 4,10 with 4,10 with 6,7,9

$1 trifecta: 4,10 with 6,7,9 with 4,10 ($6)

What to say at the betting window: Turfway Park, 12^th race, $1 trifecta 4,10 with 6,7,9 with 4,10

Good luck, and enjoy the race!