HOW HIGH CAN HE FLY?

TYRRELL WINSTON (B. 1985)
HOW HIGH CAN HE FLY?
signed and dated ‘Tyrrell Winston ’24’ (lower left)
ink on magazine ad
8 x 10 3/4 inches (20.3 cm × 27.3 cm)
Executed in 2024.

NOTES: 
Born in Southern California in 1985 and now based in Detroit, Tyrrell Winston is a multidisciplinary artist whose work examines sport, celebrity, memory, and the systems through which cultural value is assigned. His practice began with collecting discarded objects from the streets and basketball courts of Manhattan and Brooklyn. By reorganizing worn basketballs, abandoned nets, and other found materials, Winston transforms overlooked objects into records of use, aspiration, and collective experience.

In HOW HIGH CAN HE FLY?, Winston reworks a 1989 Sports Illustrated cover featuring Michael Jordan, partially obscuring the original image while preserving its now-iconic headline. The question once anticipated the limits of a rising athlete; viewed retrospectively, it carries the weight of Jordan’s transformation into a global sporting and cultural figure. Encapsulated in a PSA slab, the work occupies the space between artwork and collectible. Winston uses the visual language of authentication to examine how mass-produced ephemera acquires value through age, preservation, and its association with celebrity. By concealing much of Jordan’s image, he shifts attention from the individual athlete to the mythology constructed around him.

Winston’s work has been presented internationally, with solo exhibitions at Cranbrook Art Museum, Library Street Collective, Stems Gallery, Volery Gallery, and LANDMARK and Belowground in Hong Kong. His work is held in collections including Cranbrook Art Museum, the Columbus Museum of Art, Nike, Aimé Leon Dore, and the Detroit Pistons.

Read our interview with Tyrrell Winston here.