For the longest time, it felt Justin Trudeau could do no wrong. Even as political leaders across the west fell out of favor, Canada’s handsome Prime Minister remained a popular symbol of liberal ideas. Until this weekend.

On Saturday, Trudeau tweeted out a statement on Fidel Castro, expressing his “deep sorrow” about the death of the Cuban dictator and describing him as “a larger than life leader who served his people for almost half a century.”

Trudeau added Castro, who was a friend of his late father, was a “controversial figure” but also said the Cuban people would maintain a “deep and lasting affection for el Comandante.” He concluded it was a “real honour” to meet Castro’s family on a recent visit.

The reaction was scorching. Social media lit up with a satiric hashtag #TrudeauEulogies in which posters imagined Trudeau’s farewells to other tyrants:

Meanwhile, politicians across the globe piled on, including Senator Marco Rubio (R-FL), a Cuban-American from Miami:

Back in Canada, Trudeau’s remarks didn’t go over much better. The country’s national magazine, Maclean’s, described the episode as “Trudeau’s turn from cool to laughing stock” and said the comments exposed the Prime Minister’s “foreign policy vacuity.” Worse, it appeared to puncture a carefully cultivated public image:

Trudeau made himself synonymous with Canada. He made Canada cool again. It was fun while it lasted.

By the early hours of Saturday morning, Havana time, Trudeau was an international laughing stock. Canada’s “brand,” so carefully constructed in Vogue photo essays and Economist magazine cover features, seemed to suddenly implode into a bonspiel of the vanities, with humiliating headlines streaming from the Washington Post to the Guardian, and from Huffington Post to USA Today.

Even left-leaning outlets in Canada and elsewhere appeared uncomfortable with Trudeau’s remarks.

In response to the controversy, Trudeau attempted to defend his statement on Sunday, conceding that Castro was a dictator, but also reaffirming his original sentiments.

The fuss over the remarks will eventually pass as the media moves on to other issues. But for Trudeau, the Castro comment is likely to be remembered as a permanent tarnish on a once-beautiful brand.