[15][16] Toews joined the Progressive Conservative Party of Manitoba in 1989, winning a seat in the 1995 election, by narrowly defeating NDP incumbent Harry Schellenberg in the north Winnipeg riding of Rossmere.

One of his first ministerial decisions was to grant jail superintendents the right to institute complete smoking bans, impose random drug tests, and monitor prisoners' calls.

[25] In August 1998, Toews announced that his ministry would hire more Crown attorneys and construct more than seventy new beds for the Headingley Correctional Institution, in an attempt to incarcerate more dangerous offenders.

In March 1998, he stood with federal cabinet minister Lloyd Axworthy to announce a plan discouraging court sentences for non-violent aboriginal offenders.

[36] During a legislative debate in June 1999, Toews accused NDP Justice Critic Gord Mackintosh of mischief for repeatedly calling the province's Street Peace gang hotline only to hang up before leaving a message.

[38] He expressed interest in working with the Canadian Alliance, a successor to the Reform Party that sought to build support among Blue Tory Progressive Conservatives.

Toews endorsed Tom Long's bid for the Alliance leadership in June 2000, and approved of Brian Pallister's efforts to bring the Progressive Conservatives into cooperation with the new party.

[39] Toews formally joined the Alliance in the buildup to the 2000 federal election, and defeated four other candidates to win the party's nomination in Provencher, a primarily rural riding in southeastern Manitoba.

[43] In 2003, Toews recommended that Alliance members purchase Progressive Conservative membership cards to support the leadership bid of Jim Prentice.

[49] A Winnipeg Free Press poll taken in late December 2005 showed Toews as the most popular choice to replace Stuart Murray as leader of the Manitoba Progressive Conservatives.

Toews criticized some Supreme Court decisions, and on one occasion accused former Chief Justice Antonio Lamer of overseeing a "frenzy of constitutional experimentation".

Toews stated that the bill could restrict freedom of expression and religion, and was quoted as saying that a "homosexual activist" could sue a hotel chain to remove Bibles as hate literature.

This law had previously been used by the Royal Canadian Mounted Police to obtain search warrants for the home and office of Ottawa journalist Juliet O'Neill, after she received and published leaked information about Maher Arar.

In the same week, an Ottawa judge struck down as unconstitutional a section of the Anti-terrorism Act that defined terrorism as crime motived by religion, politics or ideology.

[64] In December 2006, Toews and Minister of Indian Affairs and Northern Development Jim Prentice announced plans to repeal Section 67 of the Canadian Human Rights Act.

NDP Justice Critic Joe Comartin argued that this change addressed the legitimate concerns of Canadians, while removing what he described as "the radical, extreme over-reaction" of the Conservatives.

[76] Civil libertarian groups also argued that the bill threatened the constitutional principle of accused persons being presumed innocent until proven guilty, and suggested that it may not withstand a court challenge.

[81] He also confirmed that his government would arm guards at the Canada-United States border,[82] and would not revive plans by the previous Liberal administration to decriminalize simple possession of cannabis.

In November 2006, Toews announced that police representatives would be appointed to the provincial judicial advisory committees that review the qualifications of potential judges.

[103] The coordinator of the group Democracy Watch was strongly critical of the changes, noting that the new rules only covered "oral and arranged communication" between ministers and government officials while exempting written correspondence and chance encounters.

[107] During a June 2008 parliamentary debate, Toews described Canadian jurist Louise Arbour, the retiring United Nations High Commissioner for Human Rights, as a "disgrace".

Liberal MP Martha Hall Findlay responded that Toews had taken Arbour's remarks "completely out of context", and described his comments as an "appalling" personal attack.

[110] In November 2007, disgraced businessman and lobbyist Karlheinz Schreiber filed an affidavit in Ontario Superior Court that contained serious accusations against former Prime Minister Brian Mulroney.

[111] In late 2007, Toews indicated that the Harper government would not prioritize funding for a new football stadium proposed by Winnipeg media mogul David Asper.

[116] On April 22, 2010, Toews was accused of political interference regarding the Conservative government’s decision to cancel plans to build an $88-million facility for the Canadian HIV Vaccine Initiative (CHVI) but managed to escape blame in the House of Commons Standing Committee on Health report.

CHVI was originally launched in 2007 and its initial cornerstone was the establishment in Canada of a pilot scale HIV vaccine manufacturing facility to produce clinical trial lots.

"[120] Public response followed, with an anonymous Twitter account posting personal information of Toews' court proceedings during his divorce, and around this time Conservative support appeared to back away from the bill and open up to amendments.

However, the judge overseeing the case did not accept this argument, saying that given Toews' legal experience, including his time as Justice Minister, meant he should have been aware of the issue when receiving a judicial document marked "DÉCISION".

[126][127] In April 2017, Canada's ethics commissioner found that Toews had broken the Conflict of Interest Act by providing advice and meeting public officials on behalf of the Peguis First Nation for the Kapyong Barracks land transfer issue.

Toews also breached the two-year cooling off period for public office holders by consulting for Norway House Cree Nation through his wife's company.