Updated on 03/08/2016 1:41PM

Smokey Image adds to McCaffery's legacy

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Barbara D. Livingston
Smokey Image will make his debut against open company competition in the San Felipe Stakes.

Nearly a decade after the death of prominent California owner, breeder, and racing-industry philanthropist Trudy McCaffery, her legacy lives on – both on the track and off.

The undefeated California-bred Smokey Image hails from a female family cultivated by McCaffery, who died at age 62 in 2007 following a battle with cancer. The colt will take his first shot against open company Saturday in the Grade 2 San Felipe Stakes at Santa Anita – the same race that his grandsire, Free House, McCaffery’s favorite runner, won nearly two decades ago.

Watching intently around the country will be dozens of racing-industry professionals who are alumni of Kids to the Cup, the organization McCaffery founded to expose young people to racing. Many have gone on to follow their dreams of working in the industry.

“She genuinely believed that giving young people access to the barns, the horsemen, and the inner workings of the sport would give us the courage and contacts to pursue our dreams, and I think she was spot on,” said California-based KTTC alum Emily Shields. “There’s no doubt that many jobs in the game are now filled by people that she helped guide, people who genuinely want to see the game thrive and grow and have fresh ideas on how to make that happen. She is still sorely missed.”

McCaffery, an accomplished equestrian in her youth, found swift success in Thoroughbred racing. Among the initial group of yearlings she purchased with her business partner, John Toffan, in 1989 were the multiple classic-placed Mane Minister and graded stakes winner Nice Assay.

The partnership returned to the Triple Crown in 1997 with Santa Anita Derby winner Free House, who knocked heads with rival Silver Charm throughout his career, finishing third in the Kentucky Derby, a tight second in the Preakness, and third in the Belmont. He went on to win the 1998 Pacific Classic and the 1999 Santa Anita Handicap, retiring with more than $3.1 million in earnings. Free House stood at California’s Vessels Stallion Farm until his death in 2004 following an accident. Upon her own death, McCaffery arranged for some of her ashes to be scattered at his grave.

“Of all our horses, he was the one who gave me the most joy,” McCaffery told DRF in 2007. “He made me proud, and he made me laugh.”

Nice Assay gave McCaffery and Toffan Came Home, who won the Hopeful Stakes, Santa Anita Derby, and Pacific Classic. They also campaigned Grade 1 winner Bien Bien and bred his best son, multiple Grade 1 winner Bienamado; they raced Grade 1 winner Pacific Squall; and they bred and sold Breeders’ Cup Distaff winner Round Pond.

Bienamado’s half-sister Madame Sunshine was unraced but produced six winners for McCaffery and Toffan, including Neeshanha. The latter was bred to Free House and sold for $9,000 to C-Punch Ranch carrying the resulting foal – Special Smoke, the dam of Smokey Image. The Southern Image colt has won all six of his starts, including a romp in the California Cup Derby last out to earn his shot at the Derby trail.

“I was very impressed,” said jockey Victor Espinoza. “For me, I don’t look at it like a Cal-bred or not. I just look at him and ask whether he has potential, whether he can have a future. The way he ran, he showed me that he can go the distance, and he showed me that he can run with any horse, Cal-bred or not.”

Smokey Image is not the only horse with a connection to McCaffery on this year’s Triple Crown trail. Came Home, standing in Japan, is the broodmare sire of three nominees, including the Wood Memorial-bound Matt King Coal and Rebel Stakes hopeful Bird of Trey.

More important, McCaffery left a legacy to racing through her work behind the scenes. In 1999, she founded Kids to the Cup, which allows kids and teens to attend races such as the Triple Crown events and Breeders’ Cup. McCaffery personally took invitees on stable tours and introduced them to industry professionals.

“Perhaps no trainer, certainly in New York, was more open to KTTC than Todd Pletcher, who had only started training a few years prior,” said Susie Raisher, another KTTC alum. “Long before he was winning Eclipse Awards, he routinely welcomed a group of kids into the shed row. Those who joined KTTC for the 2003 Belmont Stakes trip were introduced to an unraced 2-year-old filly. Her name was Ashado, and 11 years later, I was in attendance in a professional capacity for her induction into the Hall of Fame.”

Raisher worked in Hall of Fame trainer Shug McGaughey’s barn before going on to work for the New York Racing Association. She now works in social media for Centennial Farms and TFB Equine. Shields also worked as a groom and hotwalker in California and Kentucky before going on to work for a variety of media outlets.

Both Shields and Rashier are part of multiple Eclipse Award winner Barbara Livingston's team of photographers.

“Being involved with KTTC brought two-pronged relief for me,” Shields said. “First, I realized I was not alone as a young person that liked horse racing. I knew lots of people that barrel raced or rode jumpers but not a single one that had watched a race. Two, it helped my parents realize that the racetrack was not only a place for gamblers but also real horsemen and professionals who make their careers in the sport. It gave them a sense that I was going to be okay pursuing this passion, and it gave me a place to go to grow up with like-minded people.”

McCaffery also served on the boards of the Oak Tree Racing Association, California Thoroughbred Breeders’ Association, Breeders’ Cup, and NTRA Charities. She was an advocate for backstretch workers, serving on the board of the Edwin J. Gregson Foundation and directing memorial contributions there upon her death, and Thoroughbred aftercare, serving on the board of Tranquility Farm.

“Her devotion to the sport and to us was unwavering and selfless,” Raisher said. “Trudy was beyond vivacious, and her foresight hasn’t been matched since. It breaks my heart that she didn’t get to see what became of the kids who crowded around her.”

The author was a member of the KTTC from 2000-03.

Charlene Shaw More than 1 year ago
Can someone confirm that John Toffan is actually "the LATE" John Toffan? As of last year he and his wife were alive and kicking and I find no reference to his passing.
Kenneth R. Wiener More than 1 year ago
Ms. Shields hopefully did mean it this way but it is unfortunate she referred to gamblers on the one hand and real horsemen and professionals on the other hand. The latter would not be able to make their careers in the sport but for the former. Ms. McCaffery sounds like an amazing woman.
Barbara Bowen More than 1 year ago
Trudy was one of a kind, and kind to all.
Union_Rags More than 1 year ago
Nice story. Smoke em.
John OHara More than 1 year ago
Trudy was a real blessing to our sport. She always wanted to shine light on the racing game and then on to getting kids involved in the sport - she hired the right guy to lead her KTTC in John DeSantis who helped carry their flag as long as he possibly could. Nice to read an article to bring back fond memories of one of the real horsewomen to have graced our sport.