Josephine Gumbs-Connor is a Barrister and Solicitor of the Eastern Caribbean Supreme Court having graduated from the University of the West Indies (Cave Hill Campus) with a Bachelor of Laws with Honours and also graduated from the Hugh Wooding Law School (Trinidad) with the Legal Professional Certificate (LEC) in 1995. As the recipient of the Mathieu Sellier Memorial Prize for Best Performance in Trial Advocacy, Josephine knew that litigation was one of her passions, and she has been in active legal practice for the past 22 years as a trial advocate. Her litigation practice in criminal, civil and commercial aspects of the law has taken her through to all levels of the Courts up to the Court of Appeal with distinction. She is the Principal of her Chambers JAG Gumbs & Co which offers a multiplicity of legal services on the island of Anguilla.

Josephine is called to the Bars of Anguilla and the British Virgin Islands, having practiced in the British Virgin Islands during a few years of her career. Josephine is Notary Public, an Accredited Director from the Institute of Chartered Secretaries and Accountants and has also been an active member of both the Anguilla Bar Association in which she has served in several capacities of the Executive over the years and is also a member of the OECS Bar Association. In 2010 she was appointed as the Advisor to the Chief Minister of the Government of Anguilla on matters of policy and over the five-year term of the administration assisted the Chief Minister in Anguilla in a breadth of matters affecting their island.

She accompanied and provided advice to the Anguilla delegation on its annual official visits to the Joint Ministerial Council (JMC) in the United Kingdom where all other Heads of Overseas Territories and Crown Dependencies engaged in bilaterial discussions on matters affecting their individual territories with British Government counterparts. As part of the social commitment to her community, Josephine who is often dubbed a community activist, was the voice behind a mike as a Talk Show host on a weekly broadcast for over 7 years where she interacted with the local community and also persons abroad in a call-in programme. She also offered significant support to mentoring activities in the community. With a love for hospitality Mrs Gumbs-Connor also manages her Estate property and is the Caribbean representative of a premiere butlering school, the Magnum Butlers Academy which offers classical training and certificated programmes to persons in the Caribbean so as to uplift their hospitality skills.