Flavien Prat will ride War of Will in Monday’s Grade 1 Shoemaker Mile at Santa Anita Park. And if that doesn’t set off the irony bells and whistles – while running red flags from every mast – nothing else will.

War of Will winning 2019 Preakness
His Preakness Stakes win sandwiched between two poor outings in the other two Triple Crown races showed why War of Will was one of the most talented and unpredictable 3-year-olds last year. He’s back on turf as one of the favorites in the Grade 1 Shoemaker Mile at Santa Anita. (Image: Eclipse Sportswire)

Last May 4, Prat found himself a Kentucky Derby-winning jockey for the first time when his mount, 65/1 shot Country House, was elevated from second to first. That, courtesy of Maximum Security’s disqualification when he interfered with a horse at the top of the Churchill Downs stretch.

The horse? War of Will.

Horse racing often seems to run along a circular timeframe, where what goes around, comes around. And Prat – Santa Anita’s hottest jockey, with 15 wins in the track’s first five days and 60 overall – comes around to the first Grade 1 stakes race of the revived meet.

Shoemaker Mile Headlines a Memorable Memorial Day Card

Named after the legendary Bill Shoemaker, the career leader in stakes wins at Santa Anita with 260 and the winner of 17 consecutive winter/spring riding titles, the Shoemaker Mile is one of three graded stakes on a stacked Santa Anita Memorial Day card. The Grade 1 Gamely for 3-year-old and up fillies and mares and the Grade 2 Monrovia for fillies and mares – starring standout sprinter Jolie Olimpica – are the others.

The Shoemaker Mile doubles as the first Breeders’ Cup “Win and You’re In” Challenge. The winner gets not only an automatic entry into the Nov. 7 Breeders’ Cup Mile, but all entry fees paid. Run over the Santa Anita inside turf course, every horse in the 11-horse field comes in off at least two months rest. That’s because most of the major tracks were closed due to the COVID-19 pandemic and the one that was open – Oaklawn Park – doesn’t offer turf racing.

Speaking of layoffs, War of Will comes off a 6 ½-month break. While he may be the biggest name among the 11 horses, he is by no means the biggest lock for that Breeders’ Cup berth.

Turf to Dirt and Back Again

Trained by newly minted Hall of Famer Mark Casse, War of Will began his career as a turf horse. Winless in his four tries on turf, Casse moved him to dirt for his 3-year-old campaign last year. The result: a miserable seventh at the Kentucky Derby and a well-beaten ninth at the Belmont Stakes.

In between, however, War of Will won the Preakness Stakes with a perfect trip. It was his fourth career victory – and his last to date. The 4-year-old son of War Front hit the board only once since: a third at last fall’s Pennsylvania Derby. His last race – 6 ½ months ago – was a poor ninth at the Breeders’ Cup Classic.

Shoemaker Mile

Morning Line (jockey)

  1. Without Parole, 4/1 (Irad Ortiz Jr.)
  2. True Valour, 20/1 (Jose Valdivia Jr.)
  3. Next Shares, 12/1 (John Velazquez)
  4. Voodoo Song, 20/1 (Mike Smith)
  5. War of Will, 4/1 (Flavien Prat)
  6. Blitzkrieg, 20/1 (Drayden Van Dyke)
  7. Majestic Eagle, 20/1 (Jorge Velez)
  8. Raging Bull, 7/2 (Joel Rosario)
  9. March to the Arch, 6/1 (Victor Espinoza)
  10. Neptune’s Storm, 15/1, (Umberto Rispoli)
  11. River Boyne, 4/1 (Abel Cedillo)

So it’s back to the turf for War of Will. And back to the turf with a new rider – Prat. The question here is the usual one with War of Will: what are you going to get with an inconsistent horse who in his 14 career starts, has missed the board seven times? And your follow-up question: what are you going to get from a value standpoint when his 4/1 morning line gets hammered?

River Boyne Comes in With Plenty of Rapids

You’re going to get long looks at others, like River Boyne. The 5-year-old Irish product and winner of $1.2 million in career earnings, River Boyne is rolling again after going 0-for-7 as a 4-year-old. River Boyne won the Grade 3 Thunder Road Stakes in February, then captured the Grade 1 Frank E. Kilroe Mile a month later. His stalking style produced eight turf victories in 13 starts at Santa Anita.

With River Boyne, you have to balance his sizzling form with his outside post and the likelihood his 4/1 morning line gets bet down.

That brings us to two other intriguing candidates: one win candidate and one must-use underneath. The former is your 7/2 favorite, Raging Bull, who ships in from Florida for his 2020 debut. Trained by Eclipse Award-winning trainer Chad Brown, a wizard getting horses quickly to speed after layoffs, Raging Bull won the Grade 1 Hollywood Derby in December 2018.

Raging Bull Faces Another Test With This Field

But he’s winless in five starts since, albeit tangling with the standout likes of Bricks and Mortar and Got Stormy – two of the best older horses in North America.

Raging Bull has the late kick all great turf horses possess, has the capable Joel Rosario aboard, and is battle-tested enough against quality competition.

The other horse is Neptune’s Storm (15/1). Making his 2020 debut after a great 3-year-old season that produced four victories and top-three finishes in all 11 starts, Neptune’s Storm figures to set the pace with his early speed. He hasn’t raced since December and doesn’t figure to find the winner’s circle, but should offer a tasty price underneath in exotics.

The pick: Raging Bull.