When the rebellion began, Rolph did not join the rebels at their headquarters and the Lieutenant Governor appointed him as his emissary to deliver the government's offer of a truce.

The Canadian government granted him amnesty and he returned to Canada in 1843, later creating a new medical institution called the Rolph School in Toronto.

In 1851 he was elected to the Legislative Assembly of the Province of Canada and focused on his political career; upon the formation of the Morin-MacNab administration three years later, Rolph's priority returned to running his school.

[7] After the 13 October 1812 Battle of Queenston Heights, American forces released him in a prisoner swap with the British and he finished his journey to Canada to live on his father's farm in Port Talbot.

[9] Rolph was sent by Thomas Talbot, the colonel in charge of the militia, to York to ask for aide from the Upper Canadian government after Americans destroyed most of the mills west of Burlington.

The deputy inspector of accounts, a British government administrator, accused Rolph of accepting claims from officers who did not provide the appropriate vouchers.

[11][12] In August 1817, Rolph returned to England to solve financial problems related to his father's estate and to obtain lawyer and medical qualifications.

The group's political influence stalled government infrastructure, such as building roads throughout the colony, and made it difficult for those outside the faction to acquire land grants.

He campaigned on making land deeds easier to obtain, improving public education, and ensuring that all voters were able to participate in the election.

[26] In 1826, Rolph travelled to England to petition the Colonial Office to naturalize American citizens who had moved to Upper Canada, granting them the right to vote and sit in the Canadian provincial legislature.

[5] The British government accepted his petition, and he returned to York in September with guidance on what to include in the legislation to fulfil his request.

[31] At the beginning of the legislative session, Rolph introduced a resolution that stated the Parliament did not support the current members of the lieutenant governor's executive council, which passed by a vote of 37 to 1.

[12][58] Samuel Lount received the message and told the rebels to gather in Montgomery's Tavern north of Toronto to begin the rebellion.

[67] Rolph was expelled from the Upper Canada legislature on 20 January 1838 for helping to plan the rebellion and replaced by William Salmon the following month.

Rolph wrote a rebuttal and attempted to publish it in a periodical called The United States Magazine and Democratic Review.

This rebuttal was found among Rolph's papers after his death and published by John Charles Dent in his book Upper Canada Rebellion.

[71] In 1838, Rolph received an honorary membership to the Monroe County Medical Society, which allowed him to practise medicine without completing an examination.

[12] In 1848, Rolph worked with the board of commissioners of the Provincial Lunatic Asylum to successfully dismiss their medical superintendent Walter Tefler.

[81] In 1851, he was elected to represent Norfolk County in the Legislative Assembly of the Province of Canada and withdrew from running the administrative tasks of his medical school.

He was accused of stealing funds from the Treasury, but Rolph said he was using the money to pay moving expenses for his relocation to the Province of Canada's capital, reimbursement that was given to his predecessors.

[82] W. J. Boulton, a Tory legislator, accused Rolph of encouraging an attack on Toronto when he brought Head's truce to the rebels during the Upper Canada Rebellion.

[85] He proposed a bill called the Act for the Better Management of the Provincial Lunatic Asylum, which transferred various decision-making powers from the board of directors to the medical superintendent.

[89] Augustin-Norbert Morin abandoned his alliance with Hincks and instead formed a coalition government with Upper Canadian Tories led by Allan MacNab.

[107] Rolph opposed an 1825 bill that would have expanded clergy reserves to other Christian denominations because of its vague language concerning who could claim the land.

In defending his position, Rolph stated that he agreed with the Reform movement's principles and questioned the benefits of the more radical opinions of some of their members.

[122] Rolph used his reputation and political influence to control the governing councils of the Toronto hospitals and the medical licensing body of Upper Canada.

James Lesslie and Jesse Ketchum wanted to commission a portrait of Rolph in 1837 as a reward for his service, while Jonas Jones said he possessed a "vile and democratic heart".

[26] In his book on the Upper Canada Rebellion, John Charles Dent praised Rolph's actions and criticized William Lyon Mackenzie's leadership.

Mackenzie's sons-in-law Charles Lindsey and John King published critiques of Dent's book that disputed Rolph's influence in the rebellion.

[125] Historians have struggled to write about Rolph because he rarely described his personal feelings to others and wrote few documents expressing his political opinions.