Asia has long been seen as a key battleground between Washington and Beijing, and analysts say, because of tariffs, Trump may be ceding ground.
For one, given how complex these deals can be, Trump may be overplaying his hand by extending the deadline again, according to some observers.
“The bargaining position of the US has actually been diminished as they have revealed that their hand isn’t actually as strong as they would like,” said NUS economics professor David Jacks.
And the deals that are made could come at the cost of reshaping trade and ties built over decades.
Trump’s choice of posting the letters online, rather than through traditional diplomatic channels, could backfire, said Mr Capri, who described it as “political theatre”.
The confusion caused is a “great gift” to China, which is trying to portray itself as a stable alternative to Trump’s unpredictability, he added.
But the US market is not easy to replace – and Beijing has its fair share of tensions with countries in this part of the world, from Vietnam to Japan.
China is in the middle of its own trade negotiations with the US, although it has longer to strike a full agreement – until 13 August.
So who will win more friends in this trade war is hard to say, but the race is still on.
“Both parties see the need for a divorce,” Prof Jacks said, “but getting there will be tough and involve proceedings which will span years, if not decades.”