Keeneland: How to play the all-stakes Pick 5 on Blue Grass day

A huge day of racing awaits Saturday at Keeneland, with half a dozen graded stakes on the agenda.

The final five graded stakes, including the anticipated Blue Grass (G2), comprise an all-stakes Pick 5 with a $500,000 guaranteed pool. But there are several short-priced favorites in the sequence, and assuming they win as expected, playing narrow tickets will be the key to generating a profitable return on investment.

Let’s play the Pick 5 on a $50 budget.

Race 5: Madison (G1, 3:18 p.m. ET)

Two-time Grade 1 winner #5 Guarana (1-1) kicked off her 2020 campaign with an easy, 5 1/2-length allowance win sprinting 7 furlongs at Churchill Downs. Though her signature successes have come running long, Guarana is 2-for-2 in sprints, and she dominated her debut at Keeneland last spring by 14 3/4 lengths.

There are other talented fillies in the Madison field. #7 Mia Mischief (3-1) won the 2019 Humana Distaff (G1) and #8 Bell’s the One (6-1) is a two-time graded stakes winner at Keeneland. But the only runner we’ll use as a backup is #3 Sally’s Curlin (10-1), who has won her last five starts around one turn, including the 7-furling Hurricane Bertie (G3) at Gulfstream Park.

Race 6: Shakertown (G2, 3:51 p.m. ET)

The Shakertown is a race that frequently defies logic. The favorite hasn’t reached the winner’s circle since 2010, and the race has produced a bevy of upset winners at 8-1 or better. We could go on all day debating the merits of short-priced stakes winners #2 Wildman Jack (5-2), #8 Bound for Nowhere (5-2), #1 Extravagant Kid (6-1), #9 Texas Wedge (6-1), and #10 Totally Boss (8-1). Or, we could concede this race looks impossible on paper and hit the “all” button, with hopes of catching a longshot winner. That’s the approach I’m tempted to take.

Race 7: Ashland (G1, 4:24 p.m. ET)

#2 Venetian Harbor (6-5) looked like a star in the making when she broke her maiden by daylight and dominated the Las Virgenes (G2) by 9 1/4 lengths. The frontrunning daughter of Munnings was subsequently beaten in the 1 1/16-mile Fantasy (G3) at Oaklawn Park, but she ran a huge race in defeat. She finished second to Swiss Skydiver (who will face males in the Blue Grass) and pulled 10 3/4 lengths clear of recent Indiana Oaks (G3) winner Shedaresthedevil.

Venetian Harbor has been training up a storm in preparation for the Ashland and shouldn’t have any difficulty securing the lead. She looms as a formidable favorite, and one we’ll single at a short price.

Race 8: Jenny Wiley (G1, 4:57 p.m. ET)

It’s safe to say #4 Rushing Fall (6-5) is a “horse for the course,” considering her 4-for-5 record at Keeneland includes a frontrunning score in the 2019 Jenny Wiley. Conditioned by top turf trainer Chad Brown, Rushing Fall kicked off her 2020 campaign with a confident, frontrunning score in the 1 1/16-mile Beaugay (G3) at Belmont and appears poised to pick up a fifth Grade 1 win on her favorite course.

Race 9: Blue Grass (G1, 5:30 p.m. ET)

I’ll take a stand with the up-and-coming #3 Art Collector (5-1), who is 2-for-2 in allowance company this season. The son of Bernardini unleashed a wicked turn of foot to dominate a 1 1/16-mile event at Churchill Downs last month, when he scored by 6 1/2 lengths over next-out Indiana Derby (G3) winner Shared Sense.

Rather than spread deep, I’ll bank on Art Collector to deliver at 5-1 on the morning line.

The tickets

$2 Pick 5: 5 with ALL with 2 with 4 with 3 ($28)
$1 Pick 5: 5 with 1,2,3,7,8,9,10,11 with 2 with 4 with 3 ($8)
$1 Pick 5: 3 with ALL with 2 with 4 with 3 ($14)
Total: $50

Good luck!