Democrats in the US House of Representatives defeated a bill critical to granting the President fast-track negotiating authority on trade, dealing a huge blow to President Barack Obama's hopes of completing a landmark free trade deal with Asia.
On Friday, a measure known as Trade Adjustment Assistance (TAA), which provides aid to workers whose jobs are displaced by free trade, failed in the House 126-302 despite some personal last-minute lobbying by the President.
While Obama has faced setbacks before on the issue, this time it might just prove fatal.
The TAA and Trade Promotion Authority (TPA) - a bill that prevents Congress from amending or filibustering free trade deals - were passed as a package by the Senate two weeks ago.
On Friday, TPA passed the House, while TAA failed.
The difference means that before fast-track authority can reach the President's desk, either the Senate considers passing TPA as a standalone measure or the House finds a way to approve TAA.
Both alternatives look unlikely at the moment. It is estimated that Democrats need to provide around 120 votes in the House to get TAA passed.
As of Friday, Democratic leaders were only able to provide 40.
Unlike the standalone fast-track bill that has overwhelming support of Republicans, the aid package for workers has always been viewed as a waste of money and an unnecessary move to appease labour unions.
So, while the Republican controlled House could pass TPA without help from the Democrats, Democrats needed to do their part to get TAA through.
For the anti-trade lobby, that made TAA the perfect tool for blocking free trade.
Republican leaders did raise the possibility of taking up the TAA vote again next week but it is unclear if they will be any more successful.
President Obama had attempted to save the TAA this morning by making an unscheduled stop on Capitol Hill to try and canvass support from Democrats.
However, just before the vote on TAA, it became clear that his efforts would come up short.
House Minority Leader Nancy Pelosi picked that time to break her long silence on the issue by saying that the aid package bill fell short.
"Whatever the deal is with other countries, we want a better deal for America's workers," she said.