Trollip was born in the town of Bedford in the Eastern Cape, attended Woodridge College, and studied Agricultural Management at the University of Natal in Pietermaritzburg.
Career in politics
Trollip joined the liberal Progressive Federal Party in 1980. His political career began in earnest when he became a municipal councillor for the PFP's successor, the Democratic Party, in 1995. He was elected as provincial chairperson in 1998 and then as the renamed DA's leader in the Eastern Cape in 2002, a position he held for 15 years. Trollip served as a Member of the Eastern Cape Provincial Legislature between 1999 and 2009. He unsuccessfully ran for party leader against Helen Zille in 2007. In 2009, Trollip became a Member of Parliament in the National Assembly and after winning a leadership contest against Ryan Coetzee assumed the position of Parliamentary Leader of the DA. On 27 October 2011, Trollip was defeated in his bid for re-election as Parliamentary Leader of the DA by fellow MP Lindiwe Mazibuko. He later left the National Assembly to return to the Eastern Cape Legislature in 2013, and was the DA's premier candidate in the Eastern Cape province for the 2014 general election. During this time, Trollip was involved with Helen Zille in welcoming King Buyelekhaya Dalindyebo into the DA, despite his conviction on serious criminal charges. Dalindyebo was subsequently expelled from the DA when the conviction was upheld on appeal. In 2015, Trollip returned to national prominence within the DA. On 13 April he was announced as the DA candidate for Mayor of Nelson Mandela Bay Metropolitan Municipality in the 2016 Local Government Elections, and was also elected as the Federal Chairperson of the DA at the party's Federal Congress in May. In 2016, Trollip was referred to the South African Human Rights Commission for alleged human rights abuses and unfair labour practices at the family farm near in the Eastern Cape, allegations that he strenuously denied. The HRC later abandoned the case, citing the difficulty of investigating events alleged to have happened between the 1970s and 2000s, and that the incidents happened before the current, constitutional dispensation and involved "issues of pre-jurisdiction".
Later career
In the municipal elections held on 3 August 2016, the DA won a plurality of seats in the Nelson Mandela Bay Metropolitan Municipality, but not a majority of seats. With the help of the smaller parties United Democratic Movement, Congress of the People and the African Christian Democratic Party, Trollip was elected as mayor of that municipality. He served in the position for 2 years, under which the metro received a ratings upgrade from Moody's. Tensions soon arose between Trollip and his deputy mayor from the UDM, Mongameli Bobani, requiring frequent interventions by the respective party leaderships to mend the relationship. The relationship eventually broke down and Bobani was ousted from the coalition in late 2017. After this, Trollip faced several no-confidence motions in his mayoralty. One was tabled to be heard on 30 March 2018. The vote was postponed, because the city council meeting descended into chaos due to the actions of the opposition parties, EFF and ANC. In August 2018, the opposition finally succeeded in replacing Trollip. He was succeeded by Bobani. DA councillor Victor Manyati abstained from supporting his party's position in a speaker vote, and the DA and its supporters left the council. Bobani was then elected with 61 votes in favour, and none against. The DA legally challenged the removal of Trollip as executive mayor. The vote of no confidence in Trollip occurred after a DA council walkout and therefore the DA states that there was no longer a quorum in the council when the vote occurred. However, the high court upheld Bobani's appointment, stating that Manyathi had still been a DA member at the time and as such there was a quorum. Trollip subsequently assumed the post of leader of the opposition of the Nelson Mandela Bay council. In October 2019, he declared his intention to run for the post of Chairperson of the DA's Federal Council. The election was held later in October and Trollip lost to Helen Zille. He resigned as the party's federal chair, and resigned from all active roles within the DA on 23 October 2019, following the resignation of Party Leader Mmusi Maimane. Trollip resigned as a DA councillor in December 2019, following the ousting of Mongameli Bobani.
Personal life
He is a fluent speaker of Afrikaans, English, and Xhosa. He has two children. Trollip married Janine Handley on 5 November 2016 at Kasouga.
