He was noted for his support of liberal causes such as women's suffrage, and for his strong belief that philosophy and theory should always triumph over political expediency.

After failing to find employment as a surveyor on the Otago gold-fields, Stout returned to education, holding a number of senior teaching positions at the high-school level.

He also became one of Otago University's first students (possibly the first, although this claim is disputed), studying political economy and the theory of morality.

During his time on the Council he impressed many people - both with his energy and with his rhetorical skill - although others found him abrasive, and complained about his lack of respect for those who held different views.

He often expressed fears that private ownership would lead to the sort of "powerful landlord class" that existed in Britain.

Later, in 1885 he noted that he had already been an advocate of Georgist public finance policy long before Henry George wrote Progress and Poverty.

His partner in the practice was growing increasingly ill, and the success of his firm was important to the welfare of both Stout and his family.

His legal career, however, was probably not the only contributing factor to his resignation, with a falling out between Stout and George Grey having occurred shortly beforehand.

During his absence from parliament, Stout began to form ideas about political parties in New Zealand, believing in the need for a united liberal front.

In August 1884, only a month after returning to parliament, Stout passed a vote of no confidence in the conservative Harry Atkinson, and assumed the premiership.

Its primary achievements were the reform of the civil service and a programme to increase the number of secondary schools in the country.

In the 1887 election, Stout himself lost his seat in parliament to James Allen by twenty-nine votes, thereby ending his premiership.

At this point, Stout decided to leave parliamentary politics altogether, and instead focus on other avenues for promoting liberal views.

Ballance's deputy, Richard Seddon, had by this time assumed leadership of the party on the understanding that a full caucus vote would later be held.

Ballance's idea of a united progressive front, Stout believed, had been subverted into nothing more than a vehicle for the conservative Seddon.

John Ballance had been a supporter of women's suffrage, although his attempts to pass a bill had been blocked by the conservative Legislative Council (the now-abolished upper house of Parliament).

However, a major initiative by suffragists led by Kate Sheppard generated considerable support for women's suffrage, and Stout believed that a bill could be passed despite Seddon's objection.

While Chief Justice, Stout showed a particular interest in the rehabilitation of criminals, contrasting with the emphasis on punishment that prevailed at the time.