Bourbon Stakes 2026: Hemingway, Bold Leadership Head Wide-Open Juvenile Turf Test

The road to the Breeders’ Cup Juvenile Turf (G1) makes its final major stop Sunday at Keeneland, where 11 2-year-olds were entered for the 36th running of the $400,000 Bourbon Stakes (G2).

Mid American. Coady Photo.

The 1 1/16-mile Bourbon closes out a blockbuster Fall Stars Weekend featuring 11 stakes worth $6.35 million, six Grade 1 races and eight Breeders’ Cup Challenge “Win and You’re In” events.

The Bourbon winner earns an automatic, fees-paid berth in the $1 million Breeders’ Cup Juvenile Turf, which will be run over the same Keeneland course Oct. 30.

It’s a wide-ranging field, from proven stakes winners to lightly raced colts taking their first serious class test.

Mid American (10-1) won the Kentucky Downs Juvenile Sprint and Popcorn (6-1) took the Kitten’s Joy at Colonial Downs, making them the field’s only stakes winners. Agate (4-1), third in the Juvenile Mile at Kentucky Downs, and Heracles (15-1), third behind Popcorn in the Kitten’s Joy, hit the board in their first tries against stakes company.

Then there is Bold Leadership (7-2), still a maiden after missing by a nose and a neck in his first two starts, and a collection of maiden winners at varying stages of development: Trim Castle, Real Goodbar, Mad Mo, Hemingway and Blaring Ambition. Let Em Know also was entered but is expected to run Saturday in the Pilgrim at Belmont Park.

Hemingway Attracts Attention -- and Money

Hemingway, the 5-2 morning-line favorite, made his first experience on turf a rather emphatic one.

The $675,000 son of Constitution showed little in his debut for trainer Brad Cox, finishing eighth in a dirt sprint at Saratoga, beaten more than 20 lengths. But somebody apparently had a very different opinion when Hemingway resurfaced on turf Sept. 6 at Kentucky Downs.

Daily Racing Form’s Marcus Hersch reported that shortly before the race, Cox was told someone -- perhaps a consortium of bettors -- had wagered $50,000 to win on Hemingway.

“I looked up and he was 2-5,” Cox told Hersch.

Whoever made the wager didn't have to sweat much. Hemingway went straight to the lead and kept widening, winning the 1-mile maiden by eight lengths.

The performance was visually impressive, although the field behind him hasn't exactly distinguished itself. Sunday will tell considerably more. Hemingway jumps directly from maiden company into a Grade 2 against several horses with stakes experience and stretches another sixteenth of a mile.

Cox said Hemingway has continued to train well and recently breezed him with Bless the Broken, a 4-year-old stakes winner who is entered in Saturday’s First Lady Stakes (G1). Flavien Prat gets the mount from post 8.

Bold Leadership Keeps Knocking

Bold Leadership has yet to win in two starts, but he hasn't missed by much. 

The Todd Pletcher-trained son of Not This Time has performed well on turf and at the Bourbon distance, losing his Saratoga maiden by a nose and the With Anticipation (G3) by a neck.

Neither trip was ideal. Bold Leadership raced four to five paths wide around both turns in his debut. He then blew the break in the With Anticipation and was forced to play catch-up behind a slow pace before just missing stablemate Liam’s Law.

A cleaner trip could make the third time the charm. Bold Leadership gets Irad Ortiz, Jr. and an advantageous draw in post 3, and Pletcher knows his way to the Bourbon winner’s circle: He has won the race three times.

Don’t Overlook the Winners

Hemingway and Bold Leadership figure to take plenty of money, but Popcorn and Mid American bring something neither has: a stakes victory.

Popcorn is 2-for-2 for trainer Jonathan Thomas and already has won at Sunday’s exact distance. After taking his debut, the imposing son of Catholic Boy stepped into the 1 1/16-mile Kitten’s Joy at Colonial Downs, settled comfortably early, swung outside on the far turn and powered away to win by two lengths.

There is something to be said for a 2-year-old who has already proven that he can relax, negotiate two turns and finish the job. With Hemingway likely to be involved early, Popcorn should be able to sit behind the pace and get first run when the real racing begins.

Mid American is also 2-for-2 since trainer Jimmy DiVito moved him to turf. The son of Epicenter won a maiden at Ellis Park by 3 1/4 lengths before cutting back to 6 1/2 furlongs and taking the $750,000 Kentucky Downs Juvenile Sprint.

He now has to stretch his speed around two turns, and post 11 does him no favors.

Agate offers another intriguing alternative. The Karakontie gelding won his maiden by 4 1/2 lengths at Ellis before finishing third of 12 in the Juvenile Mile at Kentucky Downs. He never appeared entirely comfortable over that course’s undulations but still ran well enough to hit the board. A return to a more conventional turf course could help.

Heracles, third behind Popcorn in the Kitten’s Joy, already has experience at the distance, while Real Goodbar comes back from a fourth-place finish in stakes company.

A Little Bourbon History

The Bourbon dates to 1991, when it was inaugurated as the Hopemont Stakes, named for the historic Lexington home better known today as the Hunt-Morgan House. Its first winner came with a familiar Keeneland name aboard: Hall of Famer Pat Day guided 1-2 favorite Stress Buster to victory.

The race became the Bourbon County Stakes in 2003, was shortened to the Bourbon Stakes in 2005 and was elevated to Grade 2 status in 2020. Its roster of winners includes champion Gio Ponti, Twilight Meteor and Interactif.

And there is a timely reminder that the Bourbon can produce a good horse even if he doesn't win the Breeders’ Cup a few weeks later. Minaret Station, a 38-1 winner of the Bourbon in 2024, earned his first Grade 1 victory Thursday in the Joe Hirsch Turf Classic (G1) at Belmont Park.

Curiously, no horse has gone directly from winning the Bourbon to victory in the Breeders’ Cup Juvenile Turf. Airoforce came tantalizingly close in 2015 — the last time the Breeders’ Cup was held at Keeneland — winning the Bourbon before missing by a neck in the Juvenile Turf.

Betting Angle

Hemingway might turn out to be every bit as good as that eight-length Kentucky Downs romp suggested. But at 5-2, bettors are being asked to assume that he is.

Bold Leadership has run well enough to win both of his races and could finally get the trip he needs. Agate has reason to improve away from Kentucky Downs, and Mid American has done nothing wrong in two turf starts.

But Popcorn at 6-1 offers an appealing combination of price and proof. He is undefeated, already a stakes winner, has won at 1 1/16 miles and has shown he can settle behind horses and finish.

In a Bourbon filled with promising 2-year-olds being asked new questions, Popcorn is the one who has already answered several of them.

The picks: 1 Popcorn 2 Bold Leadership 3 Mid American

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