[4][5] Prior to entering politics Osborne worked for Statistics Canada, Small Business Enterprise, and with the Penney Group of Companies.

Osborne was re-elected in the 1999 election and though the PC's had gained 5 seats the Liberals still won a large majority government.

With the victory of the Progressive Conservatives in the 2003 election[8] Premier Danny Williams appointed Osborne to Cabinet as the Minister responsible for Environment and Labour.

During his time as Minister of Health more information on errors in hormone receptor breast cancer testing were coming to light.

[11] In 2008, Osborne testified at the Commission of Inquiry on Hormone Receptor Testing and was asked about his time as Minister of Health.

In September 2012, Osborne resigned from the Progressive Conservative party citing the leadership of Premier Kathy Dunderdale and began sitting as an Independent.

[14] In the 2015 election the Liberal Party won control of the House of Assembly and Osborne was chosen as Speaker.