Mr. Connolly is a newcomer to politics, describing his bid for a seat in the Legislative Assembly as something that was “inconceivable” two months ago.
“People who love their country can change it,” Mr. Connolly said. “Some of our previous statesmen recognized this. It is through political will, hard work and perseverance that we can move Cayman forward in the right direction.”
Mr. Connolly said his campaign would focus on struggling families, professional advancement and education, as well as global challenges facing all Cayman residents. He believes Caymanians should demand a more accountable government.
“We need all hands on deck,” Mr. Connolly said. “The time for partisan politics is over. We need to work together and use all the resources we have to right the Good Ship Cayman. In so doing, we may better understand each other and move ahead as a stronger community and country that is based on mutual respect and understanding of each other.
“Politics which shuts you out if you are in the “wrong” party, politics which tells you to settle for the status quo only divides us all. Our heritage was built on the premise that we are one people. That belief helped to create a Cayman that ensured a high standard of living for all. We can become one people again.”
Winston is the son of Churchill and Tania Connolly of North Side and George Town, respectively. He grew up in Cayman and has lived in George Town for much of his life with his two brothers Dave and Mark. He attended the Cayman Islands High School after which he attended Loyola University New Orleans where he obtained a BBA in International Business and Management and the Cayman Islands Law School where he obtained an LLB (Hons) Degree from the University of Liverpool.
He later received a post-graduate degree in Law from the College of Law of England and Wales before returning to his Caymanian home. Winston practiced law with two of the largest offshore law firms before he became a partner at a boutique financial services firm in 2010.
He is married to Leslie and the couple have a son.