Mr. Rolston Anglin attended Sir John A. Cumber Primary School, and graduated from the Cayman Islands High School. Mr. Anglin received an academic scholarship from the major international accounting firm, Price Waterhouse (now PricewaterhouseCoopers), to attend University.

While at University, he was a member of the Phi Kappa Phi Honor Society and the Golden Key Honor Society. He graduated with Honours from The Ohio State University.

Mr. Anglin passed the Certified Public Accountant exam on his first attempt in 1996. He has also worked in New York City, the world's financial capital.

In April 2000, Mr. Anglin left a very lucrative professional career to represent his people. He was first elected in November 2000. Mr. Anglin served three terms as a Member of the Legislative Assembly from 2000 to 2013. During the 2009-2013 term, he was appointed the Minister of Education.

He listened to teachers and education leaders, placing public education on a firm footing and trajectory. Some of his accomplishments were:
• Re-introduction of Reception in schools
• Built expansions at various primary schools, including the Sir John A. Cumber Primary School
• Introduced the Principal Consultative Council
• Established National Professional Standards for Teachers
• Implemented enhanced graduation criteria for government high schools
• Established the Cayman Islands Further Education Centre (CIFEC)
• Established the Dual Entry Programme at the University College of the Cayman Islands (UCCI)
• Established the Passport2Success Programme
• Established the Nursing, BSc Programme at the University College of the Cayman Islands

Mr. Anglin was re-elected to Parliament after a twelve-year absence and is a member of the Governing National Coalition for Caymanians as the Minister for Finance and Economic Development, Education & Training.