Winston Connolly a GT candidate

Caymanian attorney and director Winston Connolly has announced he will vie for a seat in the electoral district of George Town during the upcoming general election in May.  

He describes his bid for a seat as something that, two months ago, was inconceivable. However, for several reasons which will be revealed during his campaign, he felt compelled to put his hat, and experience, in the ring. 

“People who love their country can change it. Some of our previous statesmen recognised this. It is through political will, hard work and perseverance that we can move Cayman forward in the right direction,” Mr. Connolly said. 

The theme of his campaign will focus on struggling families, professional advancement, education and local and global challenges facing all Cayman residents. Mr. Connolly is keen to meet with constituents to gain an understanding of their primary concerns. He would like the people who call Cayman home to know that they are heard, and it is his intention to address their concerns both on a local and international level. He is a dynamic individual who is well suited to tackle the many tough and dynamic issues that we face as a government and a territory. He acknowledges that there are several challenges ahead, but he’s enthusiastic and determined to face them. 

He believes that as an individual, he is not THE answer. But together, with like minded, patriotic Caymanian leaders, willing to put their careers and lives on hold, to secure the future of Cayman for its current and future generations, no problem is too big to resolve. He only asks that voters who want, and by all rights should demand, a more accountable government and a better Cayman, come out to support him and other like-minded individuals. 

“We need all hands on deck. 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,” Mr. Connolly said. 

“Politics shut you out if you are in the ‘wrong’ party, which tells you to settle for the status quo that 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, striving for a common goal. Let us reach out for what is possible and build a better Cayman,” he said. 

Mr. Connolly 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 in New Orleans, where he obtained a bachelor’s degree in international business and management and the Cayman Islands Law School where he obtained an undergraduate law degree with honours 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 Cayman. 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 Lesley, a fifth generation Caymanian and is father to Wade. 


The Caymanian Compass will publish candidate’s announcements and letters to the editor from them and their supporters, at the Editor’s discretion and with proper editing for style and libel, until 1 March, 2013. Candidates who purchase advertising will have their initial announcement declaring their intention to run for office on Page 1 for one time only. 


  1. A very warm welcome, Mr Connolly, to the political arena. I wish you every success, as long as you continue to plough the honest furrow which you have laid out for yourself; and I fervently hope more like-minded Caymanians will put their shoulders to the wheel.

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