Born in Dunedin and educated at King's High School, Benson-Pope received his tertiary education at the University of Otago and at the Christchurch College of Education. While studying education he was president of the Students' Association at the college, and National President of the Student Teachers' Association of New Zealand. He became involved in the teachers' unions working as a teacher and was first elected to the Dunedin City Council in October 1986. He remained a city councillor for five terms until 1999, when he successfully contested the Dunedin South electorate for the Labour Party.
Benson-Pope was temporarily stood down as a cabinet minister in 2005 after allegations from former students about the use of violence in the class room. The allegations included stuffing a tennis ball in 14-year-old's mouth, throwing tennis balls at students to keep them quiet, striking a pupil with the back of his hand making the pupil's nose bleed at a school camp, and caning a student hard enough to draw blood. Benson-Pope denied the allegations. Investigate magazine published, in February 2006, allegations that he entered the girls' dormitory to awaken students twice, and that he told them once that they were taking too long to shower after a "mud run." Benson-Pope denied any impropriety.
Benson-Pope faced further controversy in 2007, which led to the resignation of his ministerial posts and the end of his Parliamentary career. In 2007 he resigned the Ministerial posts and resumed the role of a backbencher representing the Dunedin South electorate. In 2008 he sought to recontest the Dunedin South seat on behalf of the Labour Party but was not chosen as the Labour Party representative for the seat. In July 2007 it emerged that a political advisor in Benson-Pope's office made phone calls which led to the sacking of the Ministry for the Environment's newly appointed Communications Manager. The issue revolved around her relationship with the chief press secretary to National's parliamentary leader John Key, despite the fact that she had "made a disclosure of her personal connections" during the appointment process. . After a week of intense pressure focusing not only on the allegation that his staff had acted improperly, but also that he himself had misled Parliament, the media and his Prime Minister about his knowledge and involvement, Benson-Pope offered his resignation from Cabinet at noon on Friday 27 July 2007. Subsequent investigations by the State Services Commissioners Hunn and Prebble make it clear that neither the Minister nor his staff acted in any way inappropriately. Prime Minister Helen Clark accepted the resignation, saying: "The way in which certain issues have been handled this week has led to a loss of credibility and on that basis I have accepted Mr Benson-Pope's offer to stand aside". An editorial commented "Not for the first time, he and the Government have been embarrassed less for what he has done than for his inability to simply say what he has done." Although Benson-Pope was later cleared of any wrongdoing in this case, he remained a backbencher for the remainder of the parliamentary term.
Later career
In 2008, Benson-Pope was invited to join the Aotearoa Legalise Cannabis Party by leader Julian Crawford, but he declined, saying, "Their judgement has obviously been impaired by their recreational habits". Benson-Pope then sought the nomination of the Labour Party to contest the Dunedin South electorate in the 2008 general election but ultimately was not chosen by the party. His successor, Clare Curran, was duly elected. Returning to Dunedin, Benson-Pope worked as a resource consent manager and sought election to the Dunedin City Council in the 2013 local body elections. He stood as an independent candidate and was elected on 12 October 2013. On 26 February 2015, Benson-Pope announced that he would contest the 2016 local body elections under the "Local Labour" ticket. During a live-streamed Zoom meeting of the city council held on 5 May 2020 Benson-Pope was seen in the camera of his computer cleaning his study with a feather duster whilst "pants-less". Members of the public, councillors and senior managers watched on as the meeting faced technological difficulties. Benson-Pope said he was not wearing pants but was wearing shorts after gardening earlier in the day and stated he was "delighted" that his cameo provided a welcome diversion but "It wasn't intentional."
