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Background
In the 1820s, citizens in places around the world questioned government reforms proposed by the ruling aristocracy. In Upper Canada, the ruling class was the Family Compact, colloquially called the Tories. They would often appoint their members to political positions, believing their rule would provide more economic prosperity and political stability than leaders chosen through a democratic process. Those opposed to their rule were called reformers and wanted to expand the rights of citizens, particularly recent immigrants to Upper Canada.

George Rolph was appointed to as a clerk of the peace for Gore county in 1816. This position gave Rolph power over government affairs in the region and required him to work closely with other members of the Tory elite. Rolph refused to associate with the Tories socially, avoiding galas and declining to give a toast at parties. He also refused to use his position to support the entrenchment of the ruling aristocrats, causing them to be hostile towards him. Many of the Tory elite believed that if George was convinced to leave his position, they could have another clerk appointed who would be friendlier to implementing Tory objectives.

Rolph was a reformer and his brother John Rolph was elected to the Legislative Assembly of Upper Canada in 1824 under the Reform party label. John proposed that members of the Legislative Council of Upper Canada should be elected rather than appointed to their positions; this change would make it more difficult for Tories to become members of this body. This and other Reform proposals caused the elite of Gore county to dislike John, and by extension his brother George. John stated in a letter that his enemies, referring to Tories, were pursuing him and George due to his opposition to Upper Canadian society.

A woman named Mrs. Evans left England with her child and travelled to Canada with George Rolph. Rolph allowed her to stay in his home, as she claimed that her husband was physically abusive towards her. Although she occupied a section of the home different from Rolph's bedroom, this arrangement caused rumours to spread that Rolph was committing adultery with Evans. A week before the incident, Evans's husband visited Dundas and tried convincing her to return to England with him.

Incident
Sometime on the night of June 3, 1826, a group of men met at the home of James Hamilton, a doctor and magistrate in Gore county. They chose to meet there because of its proximity to Rolph's home. The idea to tar and feather Rolph was probably suggested by Titus Simons; the practice was popular in New England, where Simons lived before his family fled to Canada as loyalists during the American Revolution. Other members of the group were Alexander Robertson, Simons's son-in-law, George Gurnett, Allan MacNab, and Alexander Chewett. The group dined and drank alcohol before leaving.

The group went to the inn where Mr. Evans was staying. All members of the group except one were dressed in disguises. The threatened Evans with selling his wife, then dragged him out of the inn to speak with him about the matter outside. Evans was not harmed in this altercation and stated that he was "quite satisfied" with his treatment.

The group, probably consisting of most of the same members that visited Evans, arrived at Rolph's home. They were dressed in disguises consisting of sheets for clothing, with masks or black make-up disguising their faces. The disguises were probably meant to make Rolph and other witnesses believe that the assailants were of the lower-class community, making it harder to identify them. The mob invaded the home at around midnight, dragged Rolph outside, stripped him of his clothes while beating him, and applied tar to his skin. On the way to the house, the group lost the feathers on the way to Rolph's home, so they gathered feathers from Rolph's pillow and applied them on top of the tar. This incident left Rolph half-conscious. Six men were accused of being part of this group: It was noted at the trial afterwards that Evans was not in Rolph's bed when the raid happened.

After the incident
Rolph hired his brother, John Rolph, to be his lawyer during the litigations. John advised George to wait before laying criminal charges, as it would be his word against the accused assailants. Instead, they waited until members of the group told others of their role in the incident.

Civil trial
Ten months after the incident, George filed a civil lawsuit in the District of Gore Assizes Court against the three assailants that he could identify: Simons, Hamilton and Robertson. His lawsuit was for ₤1000 each. The judge was James B. Macauly. George, as the plaintiff, retained his brother as his lawyer. The defence was represented by MacNab, Chewett, and Henry John Boulton. John Rolph raised concerns that two of the accused in the incident were lawyers for the defence. The province's lieutenant governor, Peregrine Maitland, assured those involved that the trial would be fair. The trial began in August 1827.

In the opening statement, John stated that, although hesitant to represent his brother, felt that it would be a disservice if he represented others while declining his services to a relative. He described the action as "brutal" because the assailants were members of the aristocracy in Upper Canada and should have behaved as "gentlemen". He also stressed that the incident took place at night, which he argued meant that Upper Canadian law required additional criminality to the offence. The trial was reported nationally and internationally and the audience section of the courtroom was often full during proceedings.

In the defence's opening statement, Boulton stated that the defendant's mistaken zeal to stop adultery, which they believed George was engaged in, justified their acts. After a short deliberation, the jury found Simons and Hamilton guilty and each had to pay ₤20 in damages to George.

Aftermath
Rolph appealed this decision to the Court of King's Bench in Upper Canada. Due to John Walpole Willis's removal from the bench, the two remaining judges disagreed on whether to hear the case, thus not allowing the case to be heard by them.

Maitland stated after the trial that neither Simons nor Hamilton would be reappointed as judges due to their guilty verdict in this case.

The attack was part of a series of actions by young Tory members that attacked symbols of the reform movement. Similar incidents included the Types Riot, the physical intimidation of Reformers, culminating in the death of Charles French. This series of incidents caused the Legislative Assembly of Upper Canada to form a select committee to investigate the abuse of power perpetuated by public prosecutors.

Legacy
Academics have interpreted this attack as the ruling Tory aristocrats of Upper Canada committing an attack against the developing reform movement.

As the attorney general of Upper Canada, Boulton declined to initiate a criminal trial against the defendants. This followed the general philosophy of attorney generals and solicitor generals in Canada that only cases that disturbed the public peace should be prosecuted by the government (represented by the Crown) as victims in other cases can seek justice in the civil courts. This policy allowed attorney generals such as Boulton to be hired as lawyers for civil cases, earning extra income. Reformers were infuriated with this practice, as demonstrated in this incident, as they believed the Crown should be advocates for justice and initiate criminal lawsuits in the protection of their citizens.

Reformers also disagreed with Boulton's legal argument at the trial, which stated that the defendants' actions were justified because they thought Rolph was committing a crime against public decency. In the Reformer's opinion, an attorney general tasked with defending the law stated that citizens were allowed to break various laws, contradicting the role of his position to uphold the laws.