1953 the first airfield in the Cayman Islands was opened as well as the George Town Public hospital. Barclays ushered in the age of formalized commerce by opening the first commercial bank. Following a two year campaign by women to change their circumstances, in 1959 Cayman received its first written constitution which, for the first time, allowed women to vote. Cayman ceased to be a dependency of Jamaica. During 1966, legislation was passed to enable and encourage the banking industry in Cayman.

In 1971 the governmental structure of the Islands was again changed with a Governor now running the Cayman Islands. Athel Long CMG, CBE was the last Administrator and the first Governor of the Cayman Islands. In 1991 a review of the 1972 constitution recommended several constitutional changes to be debated by the Legislative Assembly. The post of Chief Secretary was reinstated in 1992 after having been abolished in 1986.

The establishment of the post of Chief Minister was also proposed. However, in November 1992 elections were held for an enlarged Legislative Assembly and the Government was soundly defeated, casting doubt on constitutional reform. The "National Team" of government critics won 12 (later reduced to 11) of the 15 seats, and independents won the other three, after a campaign opposing the appointment of Chief Minister and advocating spending cuts.

The unofficial leader of the team, Thomas Jefferson, had been the appointed Financial Secretary until March 1992, when he resigned over public spending disputes to fight the election. After the elections, Mr. Jefferson was appointed Minister and leader of government business; he also held the portfolios of Tourism, Aviation and Commerce in the Executive Council.

Three teams with a total of 44 candidates contested the general election held on November 20, 1996: the governing National Team, Team Cayman and the Democratic Alliance Group. The National Team was returned to office but with a reduced majority, winning 9 seats. The Democratic Alliance won 2 seats in George Town, Team Cayman won one in Bodden Town and independents won seats in George Town, Cayman Brac and Little Cayman.

Although all administrative links with Jamaica were broken in 1962, the Cayman Islands and Jamaica continue to share many links and experiences, including membership in the Commonwealth of Nations (and Commonwealth citizenship) and a common united church (the United Church in Jamaica and the Cayman Islands) and Anglican diocese (although there is debate about this) as well as a common currency (until 1972). Also, by 1999, 38-40% of the population of the Cayman Islands was of Jamaican origin and in 2004/2005 little over 50% of the expatriates working in the Cayman Islands (i.e. 8,000) were Jamaicans (with the next largest expatriate communities coming from the United States, United Kingdom and Canada).

In September 2004, The Cayman Islands were hit by Hurricane Ivan, causing mass devastation, loss of human and animal life (both wild and domestic/livestock) and flooding, with some accounts reporting that 25% or more of Grand Cayman had been underwater and with the lower floors of buildings being completely flooded. This natural disaster also led to the bankruptcy of a heavily invested insurance company called Doyle.

The company had re-leased estimates covering 20% damage to be re-insured at minimal fees when in fact the damage was over 65% and every claim was in the millions. The company simply could not keep paying out and the adjusters could not help lower the payments due to the high building code the Islands adhere to. Much suspense was built around the devastation that Hurricane Ivan had caused as the leader of Government business Mr. Mckeeva Bush decided to close the Islands to any and all reporters.

This led to severe reports in the media of hundreds dead, when in fact none but two that refused to stay in the shelters were lost. It was also a collective decision within the government at that time 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.

However, when the Island re-opened in early December to tourists the cruise ships once more started to pour in, all intrigued to see the damage. While there were visible signs of damage, in the vegetation and an apparent lack of construction in some places, the Island was bustling again as some things had been freshly re-built and those that were not were quite on their way. There remain housing issues for many of the residents as of late 2005.

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