The prime minister is facing criticism at home and abroad for his statement expressing "deep sorrow" about the death of former Cuban president Fidel Castro.
Justin Trudeau, who recently returned from a diplomatic visit to Cuba, made the statement early Saturday after the announcement that Castro had died at the age of 90.
Trudeau acknowledged the late president was a "controversial figure," but remembered him as a "larger-than-life leader," who made significant improvements to Cuba's education and health-care systems.
"A legendary revolutionary and orator, Mr. Castro made significant improvements to the education and health care of his island nation," Trudeau said.
"I know my father was very proud to call him a friend," he added.
But others in Canada — and around the world — were less generous in their description of the deceased, and some have condemned the prime minister's statement, pointing out human rights violations during Castro's half-century regime.
Marco Rubio, the Cuban-American senator for Florida, wrote on Twitter, "Is this a real statement or a parody? Because if this is a real statement from the PM of Canada it is shameful (and) embarrassing."
Conservative leadership hopeful Lisa Raitt wrote on Facebook that Trudeau should be ashamed of himself after his remarks.
"With those words, Justin Trudeau has placed himself on the wrong side of history – against the millions of Cubans yearning for freedom. The prime minister should be ashamed of himself. He must retract this statement and apologize," she wrote.
Others running to be party leader also weighed in, including Maxime Bernier and Kellie Leitch.
Foreign Affairs Minister Stephane Dion noted Castro's death by tweeting: "An iconic figure of the 20th century passed away last night. Deepest condolences to the people of #Cuba, following the death of Fidel Castro."
Robert Wright, who wrote the book "Three Nights in Havana" about the relationship between Castro and Pierre Trudeau, said it made sense Trudeau would express warm condolences for Castro.
"He has to walk a knife's edge," he said. "Canadians have a long, rather proper diplomatic relationship with revolutionary Cuba."
"On the one hand Justin Trudeau has his family inheritance: his father's very, very warm friendship with Fidel Castro, and Justin's own warm rapport with the Cubans," Wright said. "And on the other hand, he has to face criticism when Raul Castro says Cuba will take its own time on democratic reforms and won't be rushed by Obama or Justin Trudeau or anyone else."
Castro acted as an honorary pallbearer at Pierre Trudeau's funeral, along with Leonard Cohen, former U.S. president Jimmy Carter and the Aga Khan.
In his statement, Trudeau offered his condolences "on behalf of Canadians," a move Wright said is likely to upset some Canadians who wouldn't want to be included in such "warm remarks."
Trudeau's former foreign policy adviser Roland Paris was among those taking the prime minister to task, saying on Twitter "It's not a statement I would have recommended."
Trudeau's comments also garnered criticism in the United States, a long-time political adversary of Cuba.
Website Breitbart News, which was previously run by president-elect Donald Trump's senior strategist, called the prime minister a "pretty little liar" in response to his comments.
And Ian Bremmer, an American political scientist who specializes in U.S. foreign policy, tweeted that "Cuban citizens and exiles deserve better" from Trudeau.
And social media users took the opportunity to mock the prime minister using the hashtag "#TrudeauEulogies," which imagines eulogies of dictators and criminals written in the style of Trudeau's statement.
For instance, user @MW_Johnson1 wrote, "While a controversial figure, John Wilkes Booth will be remembered as a lover of the theatre."
Trudeau's office did not respond to a request for comment on the backlash.