The point where Canada’s freedom-of-speech provisions overlap with hate crime legislation is a legal, political, ethical and emotional minefield. The latest challenge, a provincial case that has reached the Supreme Court of Canada, promises to have repercussions across the country.

Bill Whatcott was charged with promoting hate after he distributed flyers in Regina and Saskatoon in 2001 and 2002 calling homosexuals sodomites and child molesters. He was found guilty by the Saskatchewan Human Rights Tribunal in 2005 and ordered to pay $17,500 to the complainants.

Whatcott argued he was opposed to gay activity, not gay people, and the Saskatchewan Court of Appeal overturned the ruling in 2010.

Bill Whatcott distributed flyers in Regina and Saskatoon in 2001 and 2002 calling homosexuals sodomites and child molesters. CBCOn Oct. 12, the case between Whatcott and the Saskatchewan Human Rights Commission went before the Supreme Court of Canada. Whatcott's lawyer, Thomas Schuck, wants the court system to lose its right to rule on hate speech. He says it's almost impossible to define hate.

Whatcott’s is the latest in a string of court challenges that have helped shape Canada’s free speech and hate crime laws, as well as their interpretation by the courts.

Here are several other notable cases that have helped set precedent for how the legal system balances what is considered a hate crime and what constitutes freedom of speech.

Telephone hate

John Ross Taylor, a self-described fascist, was jailed in Ontario in the 1980s for telephone hate messages.

In 1990, the case reached the Supreme Court of Canada, which ruled against Taylor. The majority ruled that although Canada's Human Rights Act restricts freedom of expression, that restriction is justified.

"Parliament's objective of preventing the harm caused by hate propaganda is of sufficient importance to warrant overriding a constitutional freedom," Chief Justice Brian Dickson stated in the majority opinion.

The minority opinion was written by Beverley McLachlin, now Canada's chief justice. "It is arguable whether criminalization of expression calculated to promote racial hatred is necessary," McLachlin wrote.

James Keegstra

Former Alberta school teacher James Keegstra in 1985, at the time on trial for hate mongering. The trial lasted 70 days and ended in Keegstra's conviction. Dave Buston/Canadian Press

James Keegstra had been teaching anti-Semitism to students in Eckville, Alta., for 14 years when a parent complained to the local school board about his lessons. It was 1982 and Keegstra was also Eckville's mayor.

The story received international attention and Keegstra was charged in 1984 under Canada's hate crime laws. He was convicted, but the decision was overturned on appeal after Keegstra's lawyer argued the law was unconstitutional because it violated Charter provisions on freedom of expression.

The Keegstra case continued to bounce around various courts until a landmark 1996 ruling by the Supreme Court. It said the Criminal Code section on public incitement of hatred did infringe on the Charter — but that infringement was justified — and upheld Keegstra's conviction.

Ernst Zundel

Ernst Zundel sits in a court in Germany in 2005 at the beginning of a trial where he was accused of incitement. Michael Probst/Canadian PressHolocaust denier Ernst Zundel lived in Canada for four decades, making frequent court appearances to argue for the freedom to express his anti-Semitic views in books and pamphlets and on a website.

In 1992, the Supreme Court of Canada overturned his conviction for "spreading false news," saying that the charge violated his Charter right to freedom of expression.

The German-born Zundel, who wrote the introduction to the book Did Six Million Jews Really Die?, was deported to Germany in 2005 after a Federal Court judge ruled he was a threat to national security.

He was freed from a German prison in 2010 after serving five years for denying the Holocaust.

David Ahenakew

Former leader of the Assembly of First Nations, David Ahenakew, shown in this 2008 photo, was first charged in 2002 for wilfully promoting hatred. Geoff Howe/Canadian PressDavid Ahenakew, a once-powerful leader of the Assembly of First Nations, was stripped of his Order of Canada for remarks about Jews in 2002.

During a speech at a gathering of First Nations leaders in Saskatoon, Ahenakew launched into a barely comprehensible diatribe and made anti-Semitic remarks. He repeated those comments to a reporter, and after the news was published, Ahenakew was charged with promoting hatred.

The court proceedings were protracted, but an initial conviction was overturned and, after a second trial, Ahenakew was acquitted. The Saskatchewan chief died in 2010, at 76.

Neo-Nazi custody case

Two children were removed from their Winnipeg home in 2008 after one, a seven-year-old girl, showed up at her elementary school with racist writings and symbols on her skin.

The Manitoba Court of Appeal later refused to allow the girl’s stepfather, who was accused of teaching her and his biological son neo-Nazi beliefs, to appeal a custody order giving the state permanent custody of them.

The court also dismissed a constitutional challenge from the father, who argued the government violated his right to raise the children according to his beliefs.

Cross burning

Two Nova Scotia men were convicted under Canada's hate crime laws in relation to a cross-burning incident on the lawn of an interracial couple in Windsor, N.S. (RCMP/CBC)On Feb. 21, 2010, a wooden cross was set aflame on the front lawn of an interracial couple and their children in Poplar Grove, N.S. Brothers Nathan and Justin Rehberg were convicted of public incitement of hatred, as well as criminal harassment.

Crown attorney Darrell Carmichael praised the conviction as "a really significant decision for our country." He added that, "There has never been an official court decision which states that cross-burning in this context is a hate crime."

Justin Rehberg apologized at his sentencing hearing for what he described as "a horrible mistake."