Win for the Money Stuns in Grade 1 Woodbine Mile Upset

The 5-year-old gelding Win for the Money, with only a minor stakes victory to his name, pulled off a stunning upset in the Grade 1 Woodbine Mile.

On September 14, fans flocked to Woodbine for Turf Champions Day, enjoying warm, sunny weather and a series of thrilling horse races. The day's stakes were high, with top trainers and horses vying for a spot in the Breeders’ Cup World Championships in November. By the end of the event, Woodbine’s leading trainer, Mark Casse, had claimed two of the three prestigious Grade 1 races.

The highlight of the day was the Casse-trained Win for the Money, owned by Charlotte Weber’s Live Oak Plantation. Under Hall of Fame jockey Patrick Husbands, the chestnut gelding with distinctive white markings surged up the rail to win the $1 million Rogers Woodbine Mile at longshot odds of 13-1. This marked his first Grade 1 victory and only his second stakes win of the year.

For Win for the Money’s connections, the victory was also significant for the gelding’s young sire, Mohaymen, owned by Ontario breeder Jay Hayden and standing at Northern Dawn Stable. On a day when British contenders from the powerful Charlie Appleby stable went winless, Casse’s team was ready to capitalize, propelling Win for the Money into the Breeders' Cup Mile spotlight.

Win for the Money began his career at Woodbine, breaking his maiden in 2021. After a series of races on synthetic surfaces, he transitioned to turf in 2023, winning two consecutive races (though disqualified from one) before a fifth-place finish in the Arlington Million. His subsequent graded stakes efforts saw him finish second and third before a dominant win in the Mr. Steele Stakes at Gulfstream, clocking a swift 1:38.40 for 1 1/16 miles and earning a 102 Beyer Speed Figure.

Trainer Mark Casse, keeping an eye on the Woodbine races from the Keeneland yearling sales in Lexington, had set his sights on the Woodbine Mile after Win for the Money's impressive Gulfstream win. "When he won that race, I started thinking of the Woodbine Mile for him," Casse explained. "His last two races, both riders had him sitting back when there was no pace."

In the Woodbine Mile, Win for the Money faced seven strong contenders, including the heavily favored Godolphin runner Naval Power (IRE), and another Casse-trained standout, Filo di Arianna, Canada’s two-time champion in 2022. Filo di Arianna burst out of the gate, setting quick early fractions. As he held off the challengers late, Husbands guided Win for the Money through a narrow opening along the rail to win by 1 ¼ lengths in a blistering 1:32.11, earning another 102 Beyer Speed Figure. Big Rock took third, with Naval Power finishing fourth.

A $320,000 Fasig-Tipton purchase in 2022 by Weber, Win for the Money was bred by Ken and Sarah Ramsey. His dam, Mayakoba (by War Chant), was unplaced in her career, though she produced another stakes winner, Price Tal. His fourth dam is the legendary Terlingua, the dam of Storm Cat.

This victory marked the second Woodbine Mile win for Weber, whose World Approval triumphed in 2017, and Casse’s third, following his wins with Tepin in 2018. Win for the Money rewarded bettors with a $29.30 payout.

Casse wasn’t surprised by the result. "We gave this horse a lot of time. Mrs. Weber is a big advocate of rest. Sometimes you just have to let horses develop," he said. With five wins from 15 starts and earnings of $640,938, Win for the Money is now headed to the Breeders' Cup Mile (G1) at Del Mar on November 2. Casse also hinted that Filo di Arianna could join him in the Mile.

Earlier in the day, Casse and Weber celebrated another Grade 1 victory, with And One Moe Time winning the Natalma Stakes (details in a separate article).