The Kensington and Chelsea by-election held on 25 November 1999 resulted in the return of Michael Portillo to the House of Commons. The by-election followed the death of incumbent the Conservative MP, Alan Clark.

Portillo’s loss of Enfield Southgate at the 1997 general election made him the most high-profile casualty of the ‘New Labour’ landslide. The serving defence secretary’s defeat became a symbol of Tony Blair’s electoral supremacy, inspiring the question: “Were you up for Portillo?”. The “son of Thatcher” and cabinet “bastard” had been seen as John Major’s likely successor as Conservative leader.

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Alan Clark died on 5 September 1999, aged 71. He won the Kensington and Chelsea constituency with a majority of 9,519 votes at the 1997 election.

Portillo declared his candidacy for the forthcoming by-election on 9 September. In a statement, he said: “I have informed Conservative Central Office that I wish my name to go forward for the vacancy caused by Alan Clark’s death.”

He added: “I haven’t found this a difficult decision as to contest Kensington and Chelsea would be a great privilege for any Conservative. I have no doubt therefore that there will be many excellent applicants.”

This official announcement came shortly after Portillo sought to “clear the decks” in an interview with the Times. He said he had “homosexual experiences as a young person.”

The interview followed years of speculation about his sexuality. Explaining his decision to address the speculation, Portillo said: “I’m only prepared to return to public life on my terms. That means getting these things straight.

“I’m not going to go back to public life dogged by false rumours. I’ve always intended to do that.”

Portillo’s interview prepared the ground for an acrimonious campaign.

The gay rights group OutRage!, led by Peter Tatchell, persistently confronted Portillo throughout the campaign. The group accused Portillo of hypocrisy, citing his record of voting against an equal age of consent and support for the ban on homosexuality in the armed forces. Tatchell even mulled a bid to stand against Portillo.

At one stage during the campaign, Portillo told Tatchell: “You are a horrible little man – go away”.

Portillo also angered the traditionalist Conservative right. Lord Tebbit, the former Conservative Party chairman and Thatcherite enforcer, felt compelled to respond. Tebbit accused Portillo of lying about the extent of his sexual “deviance”.

In a letter to the Spectator, Tebbit said he had supported Portillo’s comeback bid “in the belief that he had no more than a brief encounter when little more than a schoolboy, which I am told is not that uncommon”.

But he said he now understood that “his deviance continued for almost a decade”. Tebbit’s remarks were delivered in the wake of an intervention from Nigel Hart, a gay rights campaigner. In an article for the Guardian, published on 13 September, Hart said he had an eight-year affair with Portillo after Cambridge University.

Portillo’s candidacy was further overshadowed by the negative stories generated by Lord Archer’s withdrawal as the Conservative candidate for London mayor.

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However, Portillo still represented the hopes of many demoralised Conservative MPs and activists who were unconvinced by William Hague’s leadership of the party.

In the end, Portillo secured 11,004 votes (56.4%) – a majority of 6,706 over the Labour candidate, Robert Atkinson. His victory, however, was somewhat dampened by a dismal turnout of only 29.8%. The low figure was attributed by Conservative Party officials to the negative political atmosphere, as well as the affluent constituency’s mobile population.

Portillo’s comeback was completed when, mere months later, he was appointed to the shadow cabinet as deputy Conservative leader and shadow chancellor. The appointment was widely seen as a calculated move by Hague to bring a serious internal rival into the frontbencher tent.

In his first appearance in the House of Commons opposite Gordon Brown, the chancellor, Portillo said a Conservative government would “legislate to enhance” the Bank of England’s independence. He also said that “the next Conservative government” would not repeal the national minimum wage.

Brown responded: “I welcome the conversion of the Conservative Party to Labour Party policy on the Bank of England.

“I welcome, in particular, the shadow chancellor who opposed the minimum wage so vigorously when he was at the Department of Employment admitting that he was wrong and now agreeing to the minimum wage.”

During his tenure as shadow chancellor, Portillo significantly softened his Thatcherite image. He retained the Kensington and Chelsea constituency at the 2001 general election, winning a majority of 8,771 votes on a turnout of 43.3%.

Portillo subsequently stood in the 2001 Conservative leadership contest that followed Hague’s resignation as Conservative leader. The general election had produced a second successive New Labour landslide.

Sen as the ‘modernising’ candidate, Portillo won the support of 49, 50 and 53 colleagues consecutively across three rounds. He entered the race as the favourite, but was eliminated in the final round after Iain Duncan Smith rallied the eurosceptic sections of the party.

He ultimately placed third, behind Duncan Smith and veteran europhile Kenneth Clarke. Portillo chose not to serve on Duncan Smith’s frontbench, instead emerging as a tacit and sometimes explicit critic of his leadership.

Portillo’s interview and revelations ahead of the 1999 Kensington and Chelsea by-election were said to have damaged his chances in 2001. In January 2002, Clarke described a section of the Conservative Party as “not quite sure whether they were more europhobic than homophobic, or more homophobic than europhobic.”

He added: “They were the hardcore who are normally found on the hard right which had been Michael Portillo’s natural constituency until two or three years ago.”

Portillo stood down from parliament at the 2005 general election.

In 2009, Portillo began filming a show entitled Great British Railway Journeys, a series inspired by George Bradshaw’s 1863 tourist handbook.