In 1974, Redhead moved to Saint Kitts and Nevis, where he began working as a Crown Counsel. In 1975, he became Registrar of the Saint Kitts and Nevis courts and also served as a magistrate of the courts. In 1980, he became the Director of Public Prosecutions for Saint Kitts and Nevis.
In 1985, the Judicial and Legal Services Commission of the Caribbean Community appointed Redhead to be a High Court Judge of the Eastern Caribbean Supreme Court. In 1997, he became an Appeals Court Judge of the same court. Since retiring from the Court in 2003, he has twice been re-appointed as an Acting High Court Judge of the Court: from 2004 to 2006 and he was again appointed in 2007.
As a High Court Judge, Redhead has been assigned to reside in and hear cases from a number of countries, including Saint Kitts and Nevis, Montserrat, Anguilla, and Saint Lucia. His most recent appointment has been to reside in and hear cases from the British Virgin Islands.
- Eastern Caribbean Supreme Court: Territory of the Virgin Islands
- "Acting High Court Judge Appointed For Nevis and Montserrat", St. Kitts & Nevis Observer, 2011-01-14