Henry Taylor's "Jockeys and Caddies" series, which he began in 2018, is a poignant exploration of the historical presence and eventual erasure of Black athletes in predominantly white and racially exclusive sports like horse racing and golf. This body of work draws from archival photographs dating back to the 1920s and earlier, capturing moments that highlight the contributions and subsequent marginalization of Black jockeys, caddies, and professional golfers.

The series includes powerful depictions such as "HUSH NOW… you won," which illustrates the moment golfer Ben Crenshaw collapsed into the arms of his Black caddie, Carl Jackson, after winning the Masters Tournament in 1995. This painting, along with others, underscores the integral yet often overlooked roles Black caddies played in the success of white golfers. Another notable piece, "We was watching him, but they really was watching us," shows a group of Black caddies surrounding Arnold Palmer, emphasizing the racial dynamics and subordination inherent in these sports (Hyperallergic) (V21 Artspace).

Taylor's work in this series also pays homage to historical figures like Anthony Hamilton, one of the greatest jockeys, who, like many Black jockeys of his time, faced racial exclusion despite their significant achievements. The artist uses muted earth tones and sepia hues, reminiscent of old photographs, to convey the historical context and ongoing impact of racial segregation. By doing so, Taylor connects the past to the present, highlighting how these sports, and society at large, continue to grapple with issues of racial inequality (Hauser & Wirth) (Artspace).

The exhibition of this series at Hauser & Wirth Southampton also included new sculptural works and Taylor's first outdoor bronze sculpture, adding further depth to his exploration of historical and contemporary social issues. This series not only brings attention to the contributions of Black athletes but also critiques the persistent structures of racial exclusion and privilege in American society (Hauser & Wirth) (Artspace) .

Taylor's Jockeys and Caddies works are a profound narrative on race, history, and the often invisible labor that underpins celebrated achievements in sports, making it a significant contribution to contemporary art and social commentary.