O'Connor-Connolly currently serves as the Member of Parliament for the constituency of Cayman Brac East, serving her seventh term in the Parliament of the Cayman Islands.
First elected to the Legislative Assembly in 1996, she is the first woman to represent the Sister Islands. Born and raised on Cayman Brac, she first pursued a career in teaching but later received a law degree from the University of Liverpool through the Truman Bodden Law School and was a practising attorney before entering politics.
In 1997 O'Connor-Connolly became Cayman's first female minister when she was chosen to fill a vacancy on Executive Council as the Minister of Community Affairs, Sports, Women, Youth and Culture. O'Connor-Connolly had previously served as Speaker of the Legislative Assembly from November 2001 to October 2003.
From October 2003 to April 2005 she served as Minister for Planning, Communications, District Administration and Information Technology. During her tenure, Hurricane Ivan devastated the island in September 2004. O'Connor-Connolly was a minister in within the government whose collective decision at that time was to turn away two British warships that had arrived the day after the storm with supplies. This decision was met by outrage from the Islanders who thought that it should have been their decision to make.
Following one term in the opposition benches. O'Connor-Connolly was elected Deputy Premier during the Cayman Islands general election in 2009, and in addition to assuming the post of Deputy Premier, she served as Minister of District Administration, Works, Lands and Agriculture. In 2012 O'Connor-Connolly assumed the post of Premier of the Cayman Islands she also served as Minister of Finance, District Administration, Works, Lands and Agriculture.
O'Connor-Connolly was the first-ever female Premier of the Cayman Islands, serving as Premier of from 19 December 2012 until 29 May 2013.[1] Prior to becoming Premier, she was the territory's Deputy Premier serving from November 2009 until December 2012.[2]
During debate in the Legislative Assembly, following the same-sex marriage ruling by Chief Justice Anthony Smellie on 29 March 2019,[5] O'Connor-Connolly described the day of the ruling as "black Friday" for the Cayman Islands. She encouraged Caymanians to do what they could to object to the planned wedding between two women, even to the point of interrupting the wedding itself.[6] The Education Minister had used the morning prayer before the debate to refer to "cruise passengers with alternative lifestyles" causing the streets of George Town to resemble Sodom and Gomorrah.[7]
The education minister has been a fervent opponent of the Domestic Partnership Bill and any legislation that supported same-sex couples' right to a private life; describing it as "this evil that is being forced upon us". She was one of two Cabinet ministers who voted against the legislation brought by government in July to address the longstanding breach by the Caymanian authorities of Cayman's Bill of Rights and the European Convention on Human Rights.[8]
Following the 2021 Cayman Islands general election, she again crossed the floor to align with a group of independents to form a government on the morning before Parliament had its first sitting, citing that "her constituents have expressed in no uncertain terms that Cayman Brac and Little Cayman need a Minister in the Government".[9] This was her second switch of party allegiance to avoid the loss of a cabinet position.
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