Justin Trudeau Shown in 3 Separate Instances Wearing Black and Brownface Makeup

Over the past 12 hours, three separate images revealed Canadian Prime Minister Justin Trudeau had a penchant for wearing black and brownface from the time he was a teenager and well into adulthood.

The first, published by Time Magazine on Wednesday night, shows Trudeau wearing dark makeup on his face, neck, and hands for a 2001 “Arabian Nights”-themed gala at a private school, West Point Grey Academy. At the time the photo was taken, Trudeau was a 29-year-old teacher at the elite day school.

Following publication of the photo, Trudeau apologized and owned up to another similar incident, this time when he was in high school. A picture from his yearbook shows Trudeau wearing blackface to sing the Jamaican folk song and Harry Belafonte staple “Day O” at his high school talent show.

Then, on Thursday morning, a third image of Trudeau wearing blackface surfaced. In the video clip, Trudeau appears to be wearing head-to-toe blackface. A senior official of the Trudeau’s Liberal party confirmed it was the prime minister in the video, but didn’t give any additional comment to Global News Canada, which broke the story. The date or place the video was taken isn’t known.

Addressing reporters about the first brownface incident on Wednesday night, Trudeau said, “I shouldn’t have done that. I should have known better and I didn’t. I’m really sorry.”

Responding to a question about whether the photo of him was racist, Trudeau responded that it was.

“I didn’t consider it racist at the time, but now we know better,” the prime minister said about the 2001 incident, according to Time.

Trudeau’s blackface scandal hits at a crucial time for the prime minister—and for Canada. He is running for re-election and, as Time reports, polls show Trudeau neck-and-neck with the Conservative party with just five weeks left before election day.

Asked directly whether he would resign as a result of the scandal, Trudeau repeated that he took responsibility for donning blackface and that he “should have known better.”

Trudeau was widely criticized by politicians across the political spectrum as news hit of the photos, though his swift apology appeared to placate some, including the National Council of Canadian Muslims. Jagmeet Singh, who heads up Canada’s progressive New Democratic Party, shifted the attention to those who would be most hurt by Trudeau’s actions.

“Tonight is not about the Prime Minister. It’s about every young person mocked for the color of their skin,” Singh wrote on Twitter Wednesday night. “The child who had the turban ripped off their head. And those reliving intense feelings of pain and hurt from past experiences of racism. To you, I say you are loved.”

Trudeau, once a liberal darling, has been criticized for failing to live up to his promises of racial reconciliation and inclusivity, particularly as it affects indigenous Canadians. As the Guardian writes, Trudeau’s rhetoric has fallen short in terms of delivering on aboriginal rights, particularly as it pertains to land and resources.

And, as Time reports, Trudeau has already faced another scandal this campaign season; he has been accused of “[pressuring] his then-attorney general to drop corruption charges against a large Canadian engineering firm.”

The prime minister touted his advocacy of minority groups in his remarks on Wednesday.

“I have worked all my life to try and create opportunities for people to fight against racism and intolerance, and I can just stand here and say that I made a mistake when I was younger, and I wish I hadn’t,” Trudeau said.

Asked about any other potentially damaging photos he wanted to take responsibility for (before the third image in blackface came out), Trudeau said, “the fact of the matter is that I’ve always—and you’ll know this—been more enthusiastic about costumes than is sometimes appropriate.”