Complex sentence: In 2006, Castellano rode Bernardini for Mohammed bin Rashid Al Maktoum's Darley Racing, winning the Preakness Stakes, and the Jockey Club Gold Cup.
Split into simpler sentences: In 2006, Castellano rode Bernardini for Mohammed bin Rashid Al Maktoum's Darley Racing. Among his wins with Bernardini was the Preakness Stakes, and the Jockey Club Gold Cup.