He travelled all over the world with the US Merchant Marine, lived in Mexico and Sweden and eventually settled down in the Netherlands, where he "was part of the considerable contingency of expatriate African American artists".
[1][7] As a young boy growing up in Harlem, Middleton often visited the nearby Savoy Ballroom and music – jazz and classical – became important inspirations for his artistic endeavors.
Middleton struggled as an artist in the United States, due to his race and status, but he continued to refine his technique, studying with other Black creatives such as Beauford Delaney.
In 1959, after significantly advancing his technical skills and having the opportunity to showcase his art, Middleton travelled to Europe to paint, living in Spain, Sweden, France and Denmark, before settling in the Netherlands in 1961.
Because of his expatriate status, and the fact that his artwork wasn’t focused on his race, Middleton’s paintings are largely absent from African-American art collections in the United States.