After a controversial career as clerk to the Executive and Legislative Councils in
                     Perth, Henry Wakeford, whose motives and attitudes were often questioned, served as
                     
A. E. Kennedy's private secretary in Western Australia. Wakeford was nominated by Kennedy in June of 1864 to be the new Acting Colonial Secretary
                     of the Vancouver Island colony during 
William Alexander George Young's absence. Wakeford, married to a daughter of 
Sir Henry Bishop, was considered 
an ambitious and pretentious man who considered himself part of the Government House
                        ‘circle'
. Upon hearing of his appointment as Acting Colonial Secretary for 
Vancouver Island, colonials in Perth questioned his loyalty and commitment to his position in Australia.
                     
                     As expressed in several despatches and minutes by CO staff, the personal relationship
                     between 
Kennedy and Wakeford was a cause for concern. Some officials noted that the mens' personal history could have been indicative of
                     a friendship, which would call the professional legitimacy of Wakeford's nomination
                     into question. Minutes from CO staff suggest that it would have been a different matter had Wakeford
                     been from the colony. 
Cardwell and his staff noted their suspicion of 
Kennedy and Wakeford, and their involvement in 
Young's leave of absence, but nothing was ever concluded nor articulated beyond their private
                     notes.