Although he spent a significant amount of time playing sports, specifically football, as a youngster he was also quite academic and qualified in medicine at the University of Edinburgh in 1836.

[3] After working as a physician in Italy and across Europe, he emigrated to New Zealand due to problems with tuberculosis, leaving in December 1840 in hope of a cure in more suitable climate.

[8] When war broke out in 1860, Featherston criticised the Government's handling of events, and lent his influence to tribal peacemaking and keeping much of Wellington Province out of the conflict.

Despite suffering from tuberculosis and at times being unable to sit on his horse, he indeed led them and accompanied Major General Trevor Chute on his west coast campaign and march to Mount Egmont.

[2] This saga gave rise to the Featherston legend: he was described leading his men into battle "in his dressing gown, with a cigar in his mouth, having no weapon whatever with which to defend himself".

[11][12] He was described as a complex and resolute figure, awed by his peers; yet also quiet with a soft, well-spoken voice, very genial and fond of a joke.