She ran on three occasions for the Island Harbour constituency. First for the Anguilla Democratic Party in the 1999 general election and then as an independent candidate in both the 2000 and 2005 general elections.[1]
Following the 2010 Anguillan general election, Webster-Bourne was voted in as the Speaker of the House of Assembly on 27 February, the first time a woman had held the post in Anguilla's history. She replaced outgoing speaker David Carty. The Governor of Anguilla, Alistair Harrison, said of her appointment, "I believe that she holds one of the most difficult jobs in Anguilla and I wish her well in her important duties."[2]
In 2012, she admonished the Deputy Speaker of the House of Assembly, Leroy Rogers, after he criticised her publicly on Radio Anguilla. He claimed that during the passage of the Vehicles and Road Traffic Amendment Bill 2011, that Webster-Bourne should have had no opinion on whether one of the offences proposed should have been included. She reminded him that the office of speaker is non-political, but under the Anguilla Constitution Order 1982 she has such rights.[3]
In the following year, she had a public falling out with members of the opposition party who accused of not remaining neutral and allowing the ruling party the ability to legislate how they wished. She responded with a public letter published in The Anguillian, to which they said that they would place a motion of no-confidence in her within the House of Assembly.[4] This was all part of an ongoing unrest between Webster-Bourne and the opposition party, whose leader, Evans McNiel Rogers, she had removed from the chamber on multiple occasions.[5] Following the 2015 Anguillan general election, Webster-Bourne was replaced by her deputy, Leroy Rogers, as speaker on 11 May 2015.[6]