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Keeneland Picks & Predictions — October 23, 2026
It's a beautiful Friday at Keeneland — clear skies, 67°F, and the kind of autumn afternoon that makes the limestone country of Lexington feel like the center of the racing universe. With the fall meet humming along, today's 10-race card serves up a little bit of everything: maiden claimers to get things rolling, a pair of stakes races anchoring the back half, and some lively turf action in between.
The track has been playing fair on both the dirt and the grass, so pace scenario and class are going to be your two biggest levers today. We've got three races open to every TrackWiz reader, with seven premium breakdowns locked in for subscribers. Let's get into it.
Best Bets
Race 1
Maiden Claiming · 6 1/2 fur · Dirt
A deep maiden claiming opener where the TrackWiz ratings create a clear tier at the top — but with all first-time or winless runners in a 6.5-furlong dash, pace scenario and post position could shuffle the deck.
Lasting Legacy is the standout on our ratings at 86.35 — a full 14 points clear of the next horse in the field — and Jose L. Ortiz in the irons is exactly the kind of booking that signals connections are serious. The 7/2 morning line is fair but shouldn't be taken for granted in a maiden claimer where form is hard to verify. At 6.5 furlongs on dirt, Ortiz will have options to rate or press, and that tactical flexibility is a real edge in a field of unknowns.
Telecaster (6/1) grades out second on the TrackWiz model at 72.71 and matches the field-best average speed figure of 55. Trainer Hutch Holsapple doesn't have a household name, but this horse is priced right to offer place value if Lasting Legacy draws all the money. In a race this wide open, Telecaster's speed profile makes him a logical exacta complement.
Boss' Deed checks in third on our ratings at 69.06, a solid number in this field, and the 9/2 morning line suggests the market is already taking notice. Jockey Axel Concepcion is an aggressive rider who can capitalize if the pace collapses up front. He rounds out a logical trifecta wheel from the top of the TrackWiz board.
Race 2
Starter Allowance · 7 fur · Dirt
This Starter Allowance at 7 furlongs has a clear top two on the ratings sheet, but the competitive career win percentages across the field suggest a field that knows how to hit the board — making this trickier than it looks.
Sassy Princess leads our ratings at 85.62 and brings a 26% career win percentage — the second-highest in the field — which means she's a horse that wins races, not just hits the board. Tyler Gaffalione takes the mount, and he's one of the most in-demand riders in the country for a reason. At 4/1 on the morning line, she represents genuine value given how far ahead of the field she grades on the TrackWiz model. The 7-furlong dirt distance gives a versatile horse plenty of room to stalk and pounce.
Progeny grades out at 67.27 on our model and carries a 17% career win rate, and trainer Jason G. Cook puts Rafael Bejarano aboard — a rider who consistently gets horses to run their race. At 9/2, there's place value here if Sassy Princess takes the win spot and Progeny grinds to the board as a closer or stalker. He's the kind of horse who fits naturally into exactas with our top pick.
Charlee Mae (6/1) posts a 60.44 rating and a 19% career win percentage, and she gets Jose L. Ortiz — a mounting that tends to draw attention in the paddock and for good reason. Trainer Kelli Martinez has her primed for a forward effort here, and the class of a Starter Allowance suits a horse with her profile. She's the show piece that makes the trifecta worth playing.
Race 3
Maiden Claiming · 1 mi · Dirt
A massive 14-horse maiden claiming field going a mile on dirt — the biggest field of the day — and with a bunch of zeroes in the speed column and no career wins anywhere, this is a genuine guessing game with a handful of rating standouts.
Soccer Socks tops our ratings at 55.83 and draws one of the best jockeys in the country in Irad Ortiz Jr., who rarely climbs aboard without a live chance. Trainer Brad H. Cox is a consistent performer at Keeneland and has long excelled in maiden company at this track. The 7/2 morning line reflects public confidence, and the one-mile distance on dirt should suit a horse that Cox has presumably pointed specifically to this spot.
Clever One (9/2) rates at 54.17 under the TrackWiz model and gets Jose L. Ortiz in the saddle — a second star jockey booking in this field, which says something. Mark Casse is a multiple Keeneland meeting winner who knows how to spot horses in the right spots. With two Casse runners in the field (Upside Out is the other), watch for Clever One as the main stable hope given the higher rating and stronger jockey assignment.
Classic Song ties for the third-highest rating in the field at 53.33 and has Wesley A. Ward training — a barn that can fire fresh horses ready to run. The 5/1 morning line makes her an accessible show option in a field this deep and unpredictable. In a 14-horse maiden, getting a Ward horse at fair odds into your trifecta is a sound play.
We're opening the card with three free best bets that span maiden claiming and starter allowance company. Lasting Legacy (R1, 7/2 ML) and Soccer Socks (R3, 7/2 ML) both surface in maiden claiming routes where class and pace shape are especially important — horses who can settle early and sustain a run on Keeneland's stretching dirt have a real edge in these spots. Sandwiched between them, Sassy Princess (R2, 4/1 ML) takes on a starter allowance field over seven furlongs, a distance that rewards tactical speed without demanding an all-out sprint from the gate.
One thread worth noting across these early races: Keeneland's dirt has historically favored horses who can sit just off the pace and pounce in the final turn. Don't overweight pure front-runners in the 6½-furlong and one-mile routes today — closers with clean trips have been doing real damage this meet.
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Clear skies, a two-stakes card, and a field full of intriguing angles — Keeneland is delivering today. Start with Lasting Legacy, Sassy Princess, and Soccer Socks as your free best bets, and let the races build toward what should be a sharp finish with Al Ghadeer and the stakes contenders. Subscribers can find pace projections, ticket breakdowns, and our full analysis for all 10 races in the premium section. Good luck out there — race smart.