After his art history studies at Yale, David Castillo spent a decade in the secondary market selling works by the likes of Wilfredo Lam and Frida Kahlo. Stints at Yale Art Gallery and the Miami Art Museum (pre-PAMM) readied the aficionado for a critically acclaimed gallery.

Opened in 2004, when Wynwood was mostly populated by warehouses, Castillo made an immediate splash. It was an instructive experience for the city. The first show, which hosted modern art masterpieces alongside contemporary work, had one patron scratching her head, who was unaware that such works could be shown outside a museum or collection. “I had one collector ask if the real paintings could be exhibited in the space,” Castillo says, “and I replied, ‘why not?’” Castillo moved to South Beach in 2014, when he realized collectors were having difficulty maneuvering in Wynwood “because of traffic and numerous other obstacles.”

Showing a sundry roster of Miami talent, such as Adler Guerrier and Jillian Mayer, Castillo’s program hinges upon the gallerist’s credentials and capabilities as a dealer. But Castillo is quick to emphasize the artists instead. “I allow my roster of artists—whose works I have sold to MoMA, the Guggenheim, the MCA Chicago and numerous other major institutions—to speak for itself.”