In an eyebrow-raising news conference Wednesday at the UN, Trump hinted at personal animus between Lighthizer and Freeland when he claimed that he rejected a Canadian request for a face-to-face meeting with Prime Minister Justin Trudeau, a request Ottawa flatly denied making.
The U.S, Mexico and Canada have been negotiating for 13 months to modernize the three-country North American Free Trade Agreement, which dates to 1994.
In a surprise twist, Mexican Economy Minister Ildefonso Guajardo said Friday that Washington and Ottawa had told him they could reach a compromise on an updated trilateral agreement within "48 hours".
Trump says he will pursue a trade deal with or without Canada, and has repeatedly threatened to impose punitive tariffs on Canadian automobiles if a trilateral deal can't be reached. Washington already has a deal with Mexico, the third member of NAFTA.
"Most of the big issues are solved with Canada", White House trade adviser Peter Navarro said Saturday on Fox News.
Three of the major outstanding issues between Canada and the U.S.in NAFTA talks leading up to this week were Section 232 national security tariffs, NAFTA's Chapter 19 dispute resolution mechanism, and regulations around Canada's dairy sector.
Canada received support from the incoming president of Mexico, Andres Manuel Lopez Obrador, who said he wanted the agreement to remain trilateral and that Mexico would not "turn our back on Canada".
"The president was using tariffs as a tool to squeeze the Canadians", said Bruce Heyman, former United States ambassador to Canada.
U.S. Trade Representative Robert Lighthizer has argued that the United State would have to reopen negotiations with the new Mexican government if the deadline is missed, but Lopez Obrador's comments appear to call that into question. They only said they didn't request a formal meeting.
U.S. -Canada talks bogged down earlier this month, and most trade analysts expected the September 30 deadline to come and go without Canada being reinstated.
Under U.S. trade law, an agreement must be published for 60 days before it can be signed by leaders of any of the participant countries, putting negotiators on the clock to reach a deal that can be signed by November 30, Pena Nieto's final day in office.
But trade attorney Daniel Ujczo of the Dickinson Wright law firm, who follows the NAFTA talks closely, said the United States put pressure on Canada, saying there would "consequences" if it didn't reach an agreement by the end of the day Sunday. "The Americans are finding that the negotiations are tough because Canadians are tough", Trudeau said on Thursday.
But a Mexican source close to the talks said the United States had in turn agreed to drop a demand for tariffs to protect USA seasonal produce growers.
So-called Chapter 19 dispute panels, which the USA wants to eliminate from Nafta and which Canada wants to preserveAn exemption for cultural sectors which Canada wants to preserveThe use of Section 232 investigations to apply tariffs to steel, aluminum, and potentially autos.
Canada's Liberal government says it does not feel bound by the latest NAFTA deadline, and it repeated on Friday that it would not bow to USA pressure to sign a quick deal. The Trump administration could face barriers in Congress if it tries to advance a deal without Canada.