Haille Paine was founded in 1879 by Charles Gale who was later joined by Bennington Haille Paine. In 1927 Bennington was joined by his son Haille Hands Paine, and in keeping with family tradition, his grandson Haille Scott Smith became a principal partner in 1954, remaining with the firm until 2000.
An office was situated in Moss Vale and another also opened in Bowral in Wingecarribee Street. Haille Paine developed into one of the most established and well-respected law firms in the Southern Highlands.
As Haille Paine expanded, the Bowral office in Wingecarribee Street became too small and the practice relocated to the present-day heritage cottage, ‘Merrigang’ in Merrigang Street, Bowral. The Moss Vale office eventually closed so all the staff could work under one roof.
Today the practice in Bowral has four Solicitors. There are three principals: Scott Leary, Rohan McAlpine and David Allen, who is also the practice manager. Scott Leary joined the practice in 2008, Rohan McAlpine in 2014 and David Allen in 2017 when David Allen Legal merged with Haille Paine Solicitors. Kerrie Allman-Hore joined the practice as a legal clerk in 2014 and has worked as a solicitor since qualifying in July 2016. Peter Fleming, a former principal for 45 years, has retired and maintains a keen interest in the legal practice.