A respected sideman recognized as a "hot" trumpet and with a versatile ear, he played and recorded with some of the greatest jazzmen of the era, including King Oliver, Jimmy Johnson, Chick Webb and Jelly Roll Morton.

His father, a prosperous tailor and land owner, was an amateur cornet player who formed the Newport News Brass Band around 1900, playing for social clubs and funerals in the area.

[8] Jazz writer Albert McCarthy reported that Pinkett recorded three sides with Gant's band in the mid-1920s, based on an interview with Harry Cooper conducted by Charles Delaunay.

Pinkett became Morton's favorite trumpet player, recording with the band both as a member and after he left in late 1928 to play in Chick Webb's Harlem Stompers.

Pinkett's last job was in 1935 performing at Adrian's Taproom in the basement of the Hotel President in Times Square with a group led by Albert Nicholas, along with Bernard Addison, Danny Barker and Joe Watts.

Even though his alcoholism had progressed to the point that he was eventually fired for showing up drunk, in October of that year he cut six sides with the group, both as a vocalist and trumpeter, the last recordings he made.

[16] On 27 November of that year, Bailey gave birth to a daughter, Doris Louise Pinkett, in Newport News, while living with her mother and siblings.