Orlando has been a member of the OBA since his second week of law school. In the 22 years that followed, he volunteered for the Civil Litigation Section and became its Chair in 2003. During that time, he co-founded the Civil Litigation Award and Dinner and served as its inaugural Chair of the Nomination and Selection Committee.  The award ceremony and dinner is now one of the premier Gala events for the Bar in Ontario.

Following his time as Chair of the Civil Litigation Section, Orlando was appointed to the Executive of the OBA to serve in the capacity of Chair of the Advocacy, Government Relations, and Communications Committee (2005-2006).  Orlando was charged with the responsibility of making the OBA’s advocacy initiatives more pro-active. To achieve this, he promoted high quality law review in OBA’s sections, implemented a rigorous quality control program, and worked hard to secure more frequent and meaningful meetings with the Ministry of the Attorney-General (“MAG”).  Through these initiatives, law reform working groups were established along with many less formal but no less important gatherings of advocates, on the one hand, and law and policy makers, on the other.  While Chair of the AGR Committee, Orlando also set in motion the redesign and re-positioning of Briefly Speaking which began with the appointment of its first Editorial Board.

From 2006-2007, Orlando served as the Treasurer of the OBA where he maintained the tradition of conservative fiscal management, wise investments, and cost controls, while supporting initiatives that maximized the benefits of membership in the OBA.