Prime Minister Justin Trudeau’s administration was thrown into crisis when his trusted deputy, Finance Minister Chrystia Freeland, published a withering resignation letter on Monday that left him weakened at the worst possible time.

Trudeau and his cabinet have been struggling for weeks to show a united front against U.S. President-elect Donald Trump’s threat to slap 25% tariffs on Canadian goods. The prime minister’s popularity, ebbing for years, is near its lowest point ever. Provincial premiers are sniping at him. Calls for his resignation — common from rivals — are getting louder from members of his own Liberal Party.

All of that was trouble enough for Trudeau. Freeland’s parting shots, though, have pushed his government as close as it’s ever been to collapse, nine years after he swept into office promising "sunny ways.”