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Sir Lynton Crosby has a clear recollection of the day Boris Johnson took his first step on the road that would eventually see him land in 10 Downing Street.

"My wife and I were staying in London, and I saw the announcement by him that he was going to run for mayor, and it was completely chaotic.

He rode his bike into the press conference and sort of took out a couple of journalists on the way through and I turned and said to my wife, there is no way that guy will ever become Mayor of London. That proves how wrong I can be sometimes."

But even his fiercest detractors would admit that Crosby is rarely wrong. He's been called the "master of the dark arts", and the "Wizard of Oz", having led politicians to electoral success in Australia, the UK and Sri Lanka.

Crosby was in Singapore to grace the expansion of C|T Group, an international consultancy firm where he serves as executive chairman and chief executive officer. Speaking to Mothership, he recounted his long and storied career in politics.

But it all began with a failure.

Standing in Australia's 1982 federal election as a Liberal (in Australian parlance, the conservative party) candidate, Crosby turned a marginal Labor Party seat into a safe Labor Party seat, as he humorously put it.

However, it wouldn't be the end of Crosby's involvement in politics.

The Wizard of Oz

Crosby next worked as the campaign director for the Liberal Party of Australia. Under his guidance, the Liberals swept to victory in four successive federal elections, from 1996 to 2004, and made the John Howard government Australia's second-longest serving federal government in history.

Having tasted success in his native Australia, Crosby set his sights further afield. He went to the UK and managed the Conservative Party in the 2005 general election.

Although the Tories lost, it would not be Crosby's last foray into British politics.

Along came a certain blonde-haired bicyclist who had a burning ambition to become Mayor of the biggest city in the UK -- and it was off to the races.

Boris Johnson on the rise

Crosby recalls being in Australia on Christmas Eve, and getting a call from none other than George Osborne, then-Shadow Chancellor. And also David Cameron, then-Leader of the Opposition, along with "one or two" others.

"(They were asking) would I help Boris Johnson, because he'd been selected to be the candidate for Mayor, but the campaign didn't seem to be going very well. And I agreed to do that and of course, somewhat against the odds, he won that election and won again in 2012."

Crosby marked Johnson's mayoral campaigns as some of the more rewarding moments in his career. As someone who's worked closely with Johnson, he expressed a remarkably good opinion of the man.

When asked about what Johnson is really like in person, Crosby said that pretty much, what you see is what you get.

Referring to the selection press conference and the bike accident he witnessed, he said that the sense of "slight disorganisation, slightly chaotic, but on the other hand sort of genuine, is pretty much what you get and what you see when you meet him."

As a candidate, he found Johnson's "massive recognition" among the public "fascinating". He recalled people coming up to him, just shouting his name as he walked down the street.

"He has some rare ability, has some unique ability to connect with people, which you often don't see. And he's like that in private," Crosby said. He added that Johnson is "one of the least malevolent people" he's ever met, and doesn't harbour grudges.

Rough and tumble

But what of his weaknesses? Crosby said that while Johnson is "definitely not lazy", he could be "a bit ill-disciplined" at times.

He added that Johnson is more interested in "vision" than day-to-day administration, something that Crosby felt Johnson would acknowledge too.

If that's a weakness, then a politician needs to put in place a structure that communicates their vision for the country, but also deliver on that vision.

"I think that's affected...his demise as prime minister, that the infrastructure wasn't there to deliver on some of the things that he wanted to focus on and achieve," Crosby said.

Having resigned as prime minister in July 2022, rumours swirled that he would attempt to mount a comeback after his successor, Liz Truss, also resigned. However, Rishi Sunak became prime minister instead.

Johnson was recently hauled before a parliamentary privileges committee to answer questions about the pandemic-era Partygate scandal, and he may be suspended, triggering a by-election in his constituency.

With his career seemingly on the brink, how does his erstwhile political guru rate his chances of a comeback?

Comeback for Boris? Not easy.

"Comebacks are very hard in politics today," Crosby bluntly said. It's not a matter of just having the ambition to return, lots of things would have to go right. And Crosby feels that people want to give the new Prime Minister Sunak the chance to prove himself.

"I don't genuinely know whether he has the ambition to come back or not," Crosby said of Johnson, observing that a loss takes a big toll on a politician's self-esteem, requiring a lot of effort to rebuild.

Reaching back in his personal history, Crosby cited that only one politician had done so - Australia's John Howard, who lost the leadership of his party but went on to resume the position and then won four successive general elections.

"But it's very hard to do," Crosby concluded.

The next general election

Crosby cited the 2015 UK general election, where he managed David Cameron's Conservatives to a victory and a majority in their own right, as possibly the most rewarding moment in his career.

"People said the campaign wasn't going to be successful and we won an outright majority, against the odds and against the media pundits. And that was very rewarding. And we knew when we ran that campaign, that the message that we were delivering resonated with the voters."

According to Crosby, many pundits didn't understand how Cameron's campaign was connecting with the voters. They looked at public opinion polls and thought Crosby's campaign wasn't working.

Crosby's team had their own polling, and they polled to "understand what was going on", not just what people thought.

"It's diagnostic, it's like going to a doctor," he said. The campaign knew they were connecting with people in the right way, such that they could win. Crosby would be recommended by Cameron for a knighthood in his 2015/16 New Year’s honours list for ‘political service’.

The next general election

But 2015 is eight years in the past, and David Cameron has been succeeded by no fewer than four prime ministers since then. The UK's next general election must be held by January 2025, a little over a year-and-a-half from now.

The Labour Party received a thumping in the 2019 election, but currently holds a significant lead over the Conservatives in the polls.

Is there no path to victory for Sunak's Conservatives? Crosby shared some advice that could be worth a pretty penny had he been acting in an official capacity, laying out three main points.

Look to the future

First up, Crosby believes that a party needs to be forward-looking when it comes to elections.

"This election is going to be a hard-fought one. Very tough. And my advice to them is the advice that I give to all candidates.

First thing is you have to believe in something. Elections are about the future. People don't vote to thank you. When they vote, they're thinking about the future. So you've got to have a plan for the future."

Economic strength

"Now for the Conservative Party, I think one of the challenges is they've lost, at present, the mantle of economic credibility, or competence. And that's tended to be the strength," he said.

Parties could promise voters more spending on education or healthcare, but unless the economy is strong and growing, they don't have the tax revenue to fund those promises.

One of the party's strengths has been its ability to deliver the compelling message that "we're economically competent, we can manage the economy." And from that flows the credibility that the party can deliver a better future for voters and their families.

"You've really got to own the mantle of economic competence, in my book," Crosby said.

Values of the voters

However, more than economic competence, a party has to have a set of values that drive "all that you seek to do." And this may not necessarily be moral values.

In the case of Singapore, Crosby said, there is a commitment to social mobility or the chance for people to better their lives, creating policies that let voters believe if they work hard and play by the rules, they can have a better future.

Three keys to victory

"So it's very important that the Conservatives have...a story about the future, that they connect to the voters on the basis of values that align between them and the voters, and thirdly, they demonstrate competence and economic management, so they can deliver a strong and growing economy, so the country can grow, and people can benefit as a result."

Top image by Mothership.