This artwork came up for sale in 2006, with a pre-sale valuation of $1,000,000 — $1,500,000. It would eventually sell for $688,000 but is highly likely to have risen in value considerably since then. During that decade there was a growing interest in Basquiat's career from private collectors and many of these have since gone on to make huge profits in just around a decade or so. This unfortunately means that much of his last period of work is inaccessible to the public, but this prolific artist left behind over 800 paintings in total, and so there are still sufficient numbers from other parts of his career that reside in national galleries and museums. Such is the new value of his work that most smaller institutions would be unable to afford the insurance premiums of protecting such exceptionally valuable pieces today.

If we study this composition we find a series of symbols sketched into the piece, as well as multiple items of text, including some roman numerals close to the centre. Anola Gay is repeated several times in the bottom left of the piece, which is a method that the artist used many times within his career, sometimes to signal the end of something. The whole artwork is a combination of red and black lines, with Basquiat choosing oil sticks in order to accurately deliver fine lines rather than by choosing deep, thick brushed paint instead. He also liked to use collages on occasion, but not here in this technically simpler piece. The portrait here is not in quite the same style that we remember him for, but the Basquiat crown is included, something that became a large part of his signature style.

The elements found within Gringo Pilot (Anola Gay) have some connection to the work of Jean Dubuffet as well as African art, the latter being a common influence throughout the artist's career. His use of skulls was always to symbolise mortality, though his expressive heads would sometimes deliver messages around mood and character. Basquiat frequently included just a head alone, with little or no torso so that he could deliver his symbolism and not have extra parts that were unnecessarily included alongside. We find the word boxing repeated many times within this artwork, and the sport was important to Basquiat for several different reasons. Firstly, it gave opportunities to members of the Afro-Caribbean community to achieve fame and fortune, but is also more generally was a key part of the lives of his community, even for the amateur boxers who were given discipline and direction by this powerful and sometimes undervalued sport.