Frieze New York is well underway, and the art world’s power brokers have assembled in Manhattan to prowl the fair and its various satellites. Milling among the booths and openings, you might find one of the scene’s best-loved characters, and perhaps the one having the most fun: Ralph DeLuca. 

The art advisor—with his thick New Jersey accent, high-school diploma, and penchant for straight talk—may represent a departure from his profession’s typical profile. But in the more than two decades since he began his career, DeLuca has climbed the art market’s ranks, befriending and collecting high-wattage artists like George Condo and Jonas Wood, and assembling a covetable roster of deep-pocketed clients including Leonardo DiCaprio, Sylvester Stallone, and MGM Resorts.