His father was born in Cuba but was an orphan and was adopted by Virgin Islander Alvin Pickering.
[4] He later also earned a Doctor of Medicine degree from the University Hospital of the West Indies, Mona Campus.
[4] He is a fellow of the American College of Obstetrics and Gynecology, Washington, D.C.[1][4] Pickering was employed as a consultant obstetrician/gynecologist by the territory's government from 1992 until 1999.
In the 2011 general election Pickering returned to office and his National Democratic Party won an overall majority.
[9] He split from the National Democratic Party in 2019, and was voted out of office in the general election later that year.