If you have a filly who can win the Woodbine Oaks, the value of that three-year-old can skyrocket almost immediately. The Oaks, at 1 1/8 miles for Canadian-breds, is the marquee race for fillies in the country and since its inauguration in 1956, winners of the race have gone on to be highly influential in the breeding shed.

The 68th Oaks is set for this Sunday, July 23 and there may be a dozen gals seeking the big share of the $500,000 purse and a chance to continue a legacy post-racing.

It is not an exaggeration to say that many Oaks winners have been tremendous broodmares throughout the world.

Just look at GOLD STRIKE, the 2005 winner for Dick Bonnycastle and trainer Reade Baker. The granddaughter of 1984 Oaks winner CLASSY ‘N SMART (dam of Gold Strike’s sire Smart Strike) produced the 2022 Kentucky Derby (G1) winner RICH STRIKE.

This year’s good three-year-old HIT SHOW, who won the Grade 3 Gotham Stakes and was 5th in the Kentucky Derby, is a son of graded stakes winner Actress, a daughter of  2009 Oaks winner MILWAUKEE APPEAL.

And some Oaks winners have gone on to be sold for big money at auction once they have retired from racing.

ACADEMIC brought $500,000 as a broodmare prospect in 2017, two years after her upset win in the Oaks.

LEXIE LOU, by Ontario stallion Sligo Bay (Ire) and just a $7,000 yearling purchase by John Ross, sold for $300,000 to Gary Barber who went on to watch her win the 2014 Oaks.

Barber sold Lexie Lou for $1 million as a broodmare prospect and she has produced Japanese Group 1 winner Danon Scorpion.

You can pick out dozens of Oaks winners who have left their mark in Canadian breeding: Flaming Page, South Ocean and Northernette, to name a few.

Two of the most influential Oaks winners have been COOL MOOD and CLASSY ‘N SMART. 

Cool Mood, the 1969 winner for Kinghaven Farms, went on to be a stakes producer and granddam of Triple Crown winners With Approval and Izvestia plus Belmont Stakes (G1) winner Touch Gold.

Classy ‘n Smart, product of Sam-Son Farms’ foundation mare No Class, is one of Canadian racing’s most prolific broodmares. The daughter of Smarten produced Breeders’ Cup Distaff (G1) and multiple champion DANCE SMARTLY, the 1991 Oaks winner and dam of 2001 Oaks winner DANCETHRUTHEDAWN.

Classy ‘n Smart also produced Grade 1 winner and top sire SMART STRIKE.

A black-and-white photo of Classy 'n Smart winning the Oaks.

Classy ‘n Smart winning the Oaks. (Michael Burns photo)

Both Cool Mood and Classy ‘n Smart should be represented in this year’s Oaks. One of the best bred fillies expected to be competing is ME AND MY SHADOW, a daughter Violence – Silhouette by Smart Strike. Me and My Shadow, stakes placed as a two-year-old last year and seemingly a filly with improvement to offer, not only has Classy ‘n Smart on her dam’s side through Smart Strike, but her 5th dam is Cool Mood.

Another Oaks contender who has a double blast of Classy ‘n Smart and Cool Mood is Robert Marzilli’s homebred TITO’S CALLING, whose dam Unstablenthemornin has Smart Strike on her sire’s side and Cool Mood on her dam’s side.

Maiden winner GREAT KATE is inbred 5×5 to Cool Mood as her sire Souper Speedy’s granddam is the very good Daijin, a daughter of Passing Moon. Great Kate’s dam Queenie’s Gold is out of a Touch Gold mare.

BIG BRASS BED, expected to come in from New York for the Oaks, is also out of a Smart Strike mare (Precision Farming).

Entries for the Oaks will be drawn Thursday morning.

Touch Gold winning a race.

Touch Gold, out of Passing Mood, daughter of Cool Mood. (Belmontstakes.com photo)