Kentucky Derby

• • Winner 7 times (1997, 1998, 2002, 2015, 2018, 2020, 2023) – though the 2021 victory with Medina Spirit was later disqualified.

Preakness Stakes

• • Winner 8 times (1997, 1998, 2001, 2002, 2010, 2015, 2018, 2023).

Belmont Stakes

• • Winner 3 times (2001, 2015, 2018).

Triple Crown Victories

• • American Pharaoh (2015) ended a 37-year drought, the first Triple Crown since Affirmed in 1978.

  • Justify (2018) became only the second undefeated horse to win the Triple Crown.

Breeders' Cup Success

• • Multiple Breeders' Cup victories, including the Classic, Sprint, and Juvenile races.

Awards & Recognition

• • Four-time Eclipse Award for Outstanding Trainer.

  • Inducted into the National Museum of Racing and Hall of Fame in 2009.

  • Consistently ranked among the all-time leading trainers in purse earnings.

• Baffert has been at the center of medication controversies and suspensions. Notably, Medina Spirit failed a post-Kentucky Derby drug test in 2021, leading to disqualification.

• These controversies have tarnished his public image but have not erased his impact as one of the most dominant trainers in modern history.

On May 17, 2025, Umberto Rispoli didn't just win a horse race; he galloped into the history books. With a masterful and gutsy ride aboard the formidable colt Journalism, he conquered the Preakness Stakes, becoming the first Italian jockey ever to win a jewel of the American Triple Crown. It was a moment that solidified his place among the world's elite riders and marked the pinnacle of a journey that is nothing short of extraordinary.

Join us for a conversation with a man whose story is one of resilience, ambition, and relentless drive. From the tough streets of Scampia, Naples, to the winner's circles in Tokyo, Hong Kong, and Paris, Umberto has consistently proven his mettle. After dominating the Italian racing circuit and setting a national record with 245 wins in a single year, he took his talent global, capturing Group 1 victories on multiple continents.

In late 2019, he brought his saddle to Southern California, and the American racing scene hasn't been the same since. In just a few years, he has amassed nearly $50 million in earnings and guided champions like Rock Your World, Smooth Like Strait, and Going to Vegas to Grade 1 glory. His 2025 season has been particularly sensational, highlighted by victories in the Santa Anita Derby and a historic triumph at Pimlico.

What does it take to spot a diamond in the rough? In this episode, we chart the incredible career of trainer and bloodstock agent Kenny McPeek, a man whose legacy is built on skill, persistence, and an unparalleled eye for equine talent.

Born at Fort Chaffee, Arkansas, but a true son of Lexington, Kentucky, Kenny McPeek has racing in his blood. Since earning his license in 1985, he has meticulously built a reputation for transforming modestly-bred yearlings into elite competitors. His breakout moment on the national stage came in 2002 when he guided Harlan's Holiday to a Florida Derby win, only to top it months later by saddling 70-1 longshot Sarava to win the Belmont Stakes, playing the ultimate spoiler to a Triple Crown bid.

But 2024 would prove to be his most historic year yet. McPeek accomplished a rare and coveted feat, winning the Kentucky Oaks with the formidable Thorpedo Anna and then capturing the Kentucky Derby with Mystik Dan just one day later. It was the first time a trainer had swept both iconic races since 1952.

Join us as we unpack the key moments, the legendary horses, and the philosophy that has made Kenny McPeek not just a Triple Crown-winning trainer, but a true master of the sport.