The legal practice was founded in 1879 by Charles Gale, who was later joined by Bennington Haille Paine in 1901. In 1927 Bennington Paine was joined by his son, Haille Hands Paine. In keeping with family tradition, his grandson Haille Scott Smith became a managing partner in 1954 until his retirement in 2000.

The practice had an office in Moss Vale and opened a second office in Bowral in Wingecarribee Street. As Haille Paine expanded, the Wingecarribee Street office became too small and the practice relocated to a heritage cottage, ‘Merrigang’, at 22 Merrigang Street, Bowral. The Moss Vale office eventually closed so that all the staff could work under one roof.

Peter Fleming joined Haille Paine in 1969 and became the principal in 2000. Peter’s daughter, Penelope joined the practice in 2007 and her husband, Scott Leary in 2008. After 45 years with the practice, Peter Fleming retired in 2013 and Scott became the principal.  

Rohan McAlpine joined the practice in 2014. In September 2017, Haille Paine merged with David Allen Legal to form an incorporated legal practice, Haille Paine Pty Ltd. Scott was joined by David and Rohan as directors and principals of the practice. David Allen became the practice manager and is now the sole principal. Scott retired from the practice in October 2018 and Rohan became a part-time consultant in February 2021.

Haille Paine is trusted and well-respected in the Southern Highlands. The year 2019 marked the 140th anniversary of the practice; which was the first to be established in the Southern Highlands. The principal and staff of Haille Paine are excited about the practice’s next chapter and continuing to serve the community in their current premises at Suite 1, 18 Station Street, Bowral on the first floor of Bowral CBD. One of our conference rooms in Bowral CBD is dedicated to preserving historical items relating to the history of our practice. An article about the history of the practice appeared in HighLife Magazine.