Saturday’s $500,000 guaranteed All-Stakes Pick 5 at Keeneland includes three Grade 1 events and the $600,000 Blue Grass (G2) for Kentucky Derby contenders. Post time for the first leg, the $250,000 Madison (G1), is 3:18 EDT.

Here’s my thoughts on the sequence:

Race 5 – Madison Stakes (G1)

#5 Guarana, a multiple Grade 1 winner last season, improved to 3-for-3 at one-turn distances when opening the year with a 5 1/4-length allowance triumph at Churchill Downs on June 4. She was geared down in deep stretch, and the Ghostzapper filly moved forward off a sharp debut score last year, romping by six lengths in the Acorn (G1) next out. Guarana has experience over the track, breaking her maiden by 14 lengths at Keeneland, and the Chad Brown trainee looks set for a big 4-year-old campaign. She is a single.

Race 6 – Shakertown Stakes (G2)

#13 Leinster, 12-1 on the morning line, showed an affinity for sprinting on Keeneland’s turf last year and ran well when returning from a lengthy layoff at Churchill Downs last time, splitting horses in deep stretch to be a clear second after closely stalking a hot pace. That race provided valuable fitness and I like his chances with Tyler Gaffalione.

I’ll spread with #10 Totally Boss, who really came on last fall and experienced a severely troubled trip off the shelf last time; #7 Fast Boat, an eye-catching allowance scorer at Churchill last out; #8 Bound for Nowhere, who will make a title defense for Wesley Ward after rolling to a four-length decision last year; #9 Texas Wedge, who makes his third start off the layoff for Peter Miller after a respectable third in the Jaipur (G1) at Belmont; #1 Extravagant Kid, who will be running late under Joel Rosario; and #5 Just Might, who faces a class check but led wire-to-wire in the Colonel Power S. three back and figures to be sent from post 5.

Race 7 – Ashland Stakes (G1)

#2 Venetian Harbor is eligible to be lone speed from her inside post, and the classy filly looks tough to beat with Joel Rosario. If Venetian Harbor catches pressure from the outside, #3 Bonny South can take advantage. She closed strongly to win the Fair Grounds Oaks (G2) going away last time, and the lightly-raced type still has plenty of upside and appears to be thriving in morning works over the track for Brad Cox.

Race 8 – Jenny Wiley Stakes (G1)

#2 Juliet Foxtrot loves Keeneland’s turf and is my top choice. She ran a huge race when finishing second in the First Lady (G1) at Keeneland last fall, splitting female turf champion Uni (who followed with a win over males in the Breeders’ Cup Mile) and multiple Grade 1 winner Vasilika (who came back to finish a neck second in the Breeders’ Cup Filly & Mare Turf), and never looked settled when returning from a six-month hiatus in the Mint Julep (G3) last time, too close to the early pace and dueling with another speedball along the backstretch. That’s not her game, Juliet Foxtrot gets a much better trip today, and she can return to form in the second start off the layoff for Cox.

Defending champion #4 Rushing Fall, who will be tough to catch if she doesn’t catch pressure from Jolie Olimpica, and late-running #8 Toinette will be added as well.

Race 9 – Blue Grass Stakes (G2)

I’m all-in with #3 Art Collector, who couldn’t been more impressive winning a June 13 allowance at Churchill Downs with ease. He was flattered when runner-up Shared Sense came back to win Wednesday’s Indiana Derby (G3) by open lengths in track record time, and Art Collector netted Brisnet 103 Speed and 114 Late Pace numbers while romping in his first two-turn dirt start. The rapidly improving son of Bernardini wound up on the lead by default last time, but Art Collector is more than comfortable stalking the action and should a good trip just off the early leaders before launching his move on the far turn. He will have more to offer in the third start off the layoff for Tommy Drury.

50-cent All-Stakes Pick 5 wager

  • 5 with 1,5,7,8,9,10,13 with 2,3 with 2,4,8 with 3 = $21