Trudeau appeared in racist makeup several times in the past. How did it stay a secret?

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WATCH ABOVE: Federal Election 2019: 'Very unusual' for event to 'disrupt' brand of major party leader: Ipsos – Sep 19, 2019

OTTAWA — Liberal Leader Justin Trudeau says deep embarrassment, as well as ignorance, led him to keep his memories of having darkened his skin to dress up as racial minorities, more than once, a secret from his campaign teams throughout his years in politics.

“I didn’t want to talk about it with anyone, because I’m not that person any more,” Trudeau said Thursday in Winnipeg.

READ MORE: Video shows Trudeau in blackface in 3rd instance of racist makeup

Still, at a time when candidates are being caught left, right and centre for past controversial comments on social media, many political observers are scratching their heads about how evidence of more than one incident involving Trudeau, who has been familiar to Canadians since the day he was born, wearing blackface had not surfaced until now.

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Jason Lietaer, a Conservative strategist, delivered a message on Twitter to the research teams behind Trudeau’s leadership rivals, the Conservative and NDP in the 2015 campaign, as well as investigative journalists and those who have written long profiles of the Liberal leader: “You’re all fired.”

“Big miss. Everyone,” Lietaer, the president of communications firm Enterprise, said Wednesday night.

David Herle, a political consultant who was a senior adviser to Liberal prime minister Paul Martin, said it is not uncommon for candidates to avoid sharing embarrassing things from their lives, even with the teams working to get them elected.

WATCH: Trudeau addresses blackface/brownface scandal

“It’s often the case that candidates and people don’t tell you everything that is in their past, hoping that it won’t come out,” said Herle, who was the co-chair of the federal Liberal election campaigns in 2004 and 2006.

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“It is often the case that campaigns do opposition research on their own candidates for exactly that reason.”

Kevin Bosch, who used to be director of opposition research for the Liberals, said he does not think the party ever did a systematic review of Trudeau when he came on the scene, likely because the party brass expected him to share anything they needed to know.

Bosch said he was more surprised the other parties did not dig up the 2001 photo of Trudeau dressed as Aladdin, his face and hands coloured with makeup, years before Time magazine published it Wednesday night.

READ MORE: Trudeau apologizes after 2001 brownface photo published by Time magazine

The photo was in the yearbook of West Point Grey Academy, a private school in Vancouver where Trudeau was a teacher. Another image from the same event was in a school newsletter. A third shows a younger Trudeau as a student, in blackface as singer Harry Belafonte.

Bosch, who is now vice-president of public affairs at Hill+Knowlton Strategies, said the photos would likely have been even more damaging had they come out during the 2015 election campaign, when Trudeau was battling a Conservative campaign message that he was not ready for the top job.

WATCH: Sohi ‘felt pain’ when he saw images of Trudeau in racist makeup

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Sohi ‘felt pain’ when he saw images of Trudeau in racist makeup – Sep 19, 2019

“It’s been my experience that when you have a brand-new leader, people are interested in their whole record, because they’re new and you’re trying to figure out who these people are and how they might govern,” he said.

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“When they’re prime minister, people care about that record.”

Former Liberal aide Greg MacEachern said part of the problem could be that campaign teams have become overly reliant on internet research, while the photo that rocked the Trudeau campaign Wednesday night was in a yearbook from before everything had a digital version.

MacEachern also said that had Trudeau come clean about his past before it caught up with him, as he did when he told HuffPost Canada he had smoked marijuana after being elected as an MP, he could have turned it into a powerful moment about personal growth.

READ MORE: Racism can become a political flashpoint — advocates say it needs to be a conversation

“He could have tied it into a speech about the importance of understanding different points of view around racism in Canada,” said MacEachern, a senior vice-president at Proof Strategies.

That moment, potentially, could have come after two American politicians — Virginia Gov. Ralph Northam and Alabama Gov. Kay Ivey — faced their own blackface scandals earlier this year.

Asked whether that should have set off alarm bells for Trudeau, Herle said: “You’re asking a question that answers itself.”

WATCH: Nenshi says seeing Justin Trudeau racist makeup a ‘sucker punch’

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Nenshi says seeing Justin Trudeau racist makeup a ‘sucker punch’ – Sep 19, 2019

But while Trudeau kept the incidents to himself, Herle noted it is impossible he is the only person to have known about them.

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“A lot of people must have known it. A lot of people must have been at the events where it happened,” said Herle, before saying something he stressed is not meant to be an excuse for the behaviour: “I’m not sure how many white people understand that to be racist.”

On Thursday, Trudeau acknowledged that he had been one of those who hadn’t.

“I have always acknowledged that I come from a place of privilege, but I now need to acknowledge that comes with a massive blind spot,” he said.

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