When Donald Trump first stepped into the Oval Office eight months ago, sections of the business community were cautiously optimistic.
The real estate mogul was talking their language. His America First economic narrative was positive and his endless promises to spearhead a revival of previously stalwart American industries seemed genuine.
US business leaders - albeit those outside of Silicon Valley - were reasonably buoyant about their prospects under his mantle. Many were happy to align their brands with this new, straight-talking outsider. It made business sense. He was a disruptor.
However, total pandemonium in the Trump White House, and months of relentless feuds, factionalism and controversies have finally come to a head.
All in all, the last 10 days or so have been nothing short of catastrophic for Trump's presidency and have mortally wounded his relationship with US business. Both the media and the political class were already overwhelmingly stacked against him. But now, business is starting to turn its back on him too.
The final straw came just days ago. His response to a protest by white supremacists and Neo-Nazis resulting in death and mayhem in Charlottesville, has laid bare Trump's failure to understand his role and lead the nation in a time of crisis.
This lack of authority and judgement has finally tipped American businesses over the edge. Association with him is damaging their reputation. He's poisoning their brands. So his economic advisory councils have imploded and the man who once branded himself as the master of the deal now cuts a lonely figure.
First to go was the CEO of Merck, one of America's - and the world's - largest pharmaceutical companies. Then the chips began to fall. The heads of Intel, Under Armour and GE woke up, smelt the coffee, and quickly followed suit in the face of the backlash over the president's comments.
Once the scale of the crisis had set in, the race was on to see whether the walkouts would become wholesale, or the president would disband these councils in their entirety.
Trump claimed he got there first, taking to Twitter to announce their wind-up. However, unlike the boardroom-kingpin character he spun for 14 seasons on NBC's The Apprentice, corporate America just isn't taking "You're fired" for an answer.
The president's relationship with big business has always been conflicted and marred by outbursts.
On the campaign trail, in public, he launched visceral attacks on America's corporates for exporting jobs, dodging tax, and allowing foreign investors to monopolise the US economy. Yet as soon as he assumed office, the private narrative took over and he offered the top jobs in his administration to the bigwigs at these very firms.
But just last week, with a single tweet in two hours of pre-market trading, Trump's latest sucker punch against Amazon founder and CEO Jeff Bezos saw around $5.7bn briefly wiped off the online retailer's stock market valuation.
The likes of General Motors and Boeing have also been caught in the crosshairs of one of Trump's 140-character tirades. As president-elect, he also slammed the defence contractor Lockheed Martin via Twitter, which saw its valuation drop by almost $4bn.
As a maverick outsider, Trump touted his business credentials; this would more than compensate for his non-existent experience in both domestic and international politics, he said.
But his promise to lead the charge towards US economic prosperity by managing the government like his business empire depended on him having the big corporates onside. And that now seems impossible long term.
America's tech giants had already openly rejected Trump's agenda, with anti-Trump feeling so widespread that there are even murmurings of Mark Zuckerberg running against Trump in 2020 on a pro-globalisation platform.
In a frenzied effort to avoid guilt by association, businesses across the board are now following suit and taking active steps to distance themselves from the president's administration, albeit subtly, as its disjointed alliance with corporate America turns sour.
Reputation is not a commodity that can be bought, but it is the very one that businesses rely on. In order to weather the storm, the self-proclaimed master of the deal desperately needs to start dealing in the same currency as his corporate counterparts.