Canadian Prime Minister Justin Trudeau wore Blackface and brownface at least three times in his past.

The first photo, published by Time Magazine on Wednesday, shows Trudeau at an Arabian Nights-themed party in 2001 wearing a sultan costume with his face, neck and hands covered in dark paint. The picture was printed in the West Point Grey Academy’s 2000-2001 yearbook. Trudeau was an instructor at the school and was 29 years old when the photo was taken.

Time received the photo from Vancouver-based businessman and West Point Grey community member Michael Adamson. Adamson discovered the it in July and felt it should be exposed to the public. He was not at the party.

Trudeau apologized for the photo on Wednesday night.

“I shouldn’t have done that. I should have known better and I didn’t. I’m really sorry,” he told reporters.

When asked if he thinks his actions were racist, Trudeau confirmed they were.

“Yes it was. I didn’t consider it racist at the time, but now we know better,” Trudeau said.

The liberal politician also admitted he wore Blackface in high school to sing “Day-O,” a song popularized by civil rights icon Harry Belafonte.

Soon after his confession, Robert Fife tweeted a photo from the performance, reports Buzzfeed.

 On Thursday morning, a third instance of Trudeau with nonsense on his face was exposed by Global News Canada.

The publication published a video of Trudeau wearing an afro and dark makeup on his face and arms. The video was reportedly filmed in the 1990s, but the occasion is unclear. Global News obtained the video earlier in the week but waited until the video’s authenticity was confirmed. The Liberal Party, which is led by Trudeau, admitted it was real but refused to comment further.