Bill English's 27-year political career has spanned the full spectrum of success and failure, from leading the National Party to its worst-ever election defeat, to steering the country through the global financial crisis before becoming Prime Minister.
He was only 28 when he became the MP for Wallace (later changed to Clutha-Southland) in 1990, following stints as a Treasury analyst, Southland farmer and house husband while his wife Mary, a GP, worked.
After Jim Bolger led National to victory in 1996, English became Minister of Health, overseeing significant reform in the sector.
After National lost the 1999 election, he was elevated to Leader of the Opposition in 2001. He sought to broaden his appeal by taking part in a charity boxing match, but the party suffered its worst defeat in history in 2002, winning only 21 per cent of the vote.
As National continued to languish in the polls, English was replaced by Don Brash in 2003. He took over the education portfolio and kept his head down until John Key led the party to victory in 2008.
English became Deputy Prime Minister and, as Finance Minister, steadied the Government's finances through the global financial crisis and the Canterbury earthquakes, eventually bringing the books back into surplus in 2015.
During this period, he was labelled the Dipton double-dipper over his use of a ministerial housing allowance while living in a Wellington home owned by his family trust.
He was eligible for the allowance after declaring that his primary residence was in Dipton, even though he had long been based in Wellington. He eventually paid back $32,000.
His attempts to use social media have earned the attention of HBO's John Oliver.
At the end of 2016, he became Prime Minister following John Key's resignation and led the party to 44.4 per cent of the vote in last year's election. But English failed to secure a coalition deal with New Zealand First and the party was sent back to Opposition.
Praise came from across the political spectrum following his retirement announcement, including from former Canadian Prime Minister Stephen Harper.
Australian Prime Minister Malcolm Turnbull told Australian Parliament that English is a "great New Zealander".
"Bill English did an outstanding job as Finance Minister and Prime Minister. He is a great friend of Australia. The job they did in New Zealand is something that has been an example to us."
However NZ First leader Winston Peters said he would leave the words of kindness to others.
"I don't think he wants to know about sympathy or otherwise. He's a big, grown, aged man, so to speak, and he's always known how rough this game is because he's been part of it, and [been] in fact inside coups, and sooner or later it will come to haunt you. That's what's happened here."
Prime Minister Jacinda Ardern, the Green Party, and Act's David Seymour all thanked English for his public service.
"Very few serve for so long at such a high level, but garner the respect of many," Ardern said.
"He is a man of clear convictions who has always had a genuine concern for the well-being of New Zealanders, and gave a huge portion of his working life to serving on their behalf."
John Key added his voice to the well-wishers.
"Like so many Kiwis I am saddened to hear my close friend Bill English is leaving Parliament. Bill has given remarkable service to a party and a country he loves. His dry wit outstanding economic leadership and rolled Rs will be missed.
"Enjoy your new life mate."
• Becoming Prime Minister in 2016
• Getting the Government's book back into surplus in 2015, following the GFC and Canterbury earthquakes
• Overseeing reforms as Health Minister in the late 1990s
• Leading National to its worst-ever election result (21 per cent) in 2002
• The Dipton double-dipper. English paid back $32,000 from a housing allowance when he was a minister, which he claimed by saying that his primary residence was in Dipton, even though he was living in his family's Wellington residence.
• Becoming embroiled in the scandal that led to the resignation of Todd Barclay, his successor in Clutha-Southland. English said he couldn't remember who had told him about recordings Barclay had made of his staff, but later released his statement to police in which he said that Barclay had told him.