In the alleged video, which Japan's Asahi Shinbum quoted a defector with contacts inside the country as describing, a narrator explains Kim is crying that he can't improve North Korea's economy.
The defector said the video surfaced in April and high ranking members of North Korea's ruling party viewed it, possibly in an official message from Kim to the party.
In April, North Korea had already offered the US a meeting with Kim and was in the midst of diplomatic charm offensive where it offered up the prospect of denuclearization to China, South Korea, and the US.
The defector speculated that the video was meant to prepare the country for possible changes after the summit with Trump.
In North Korea, Kim is essentially worshipped as a god-like figure with an impossible mythology surrounding his bloodline. Kim is meant to be all powerful, so footage of him crying at his own impotence to improve his country's economics would be a shock.
Kim's core policy as a leader was to pursue both economic and nuclear development, but around the turn of 2018, he declared his country's nuclear weapons completed.
Experts assess with near unanimity that Kim doesn't really want to disarm his country, as he went to the trouble to write the possession of nuclear weapons into North Korea's constitution.
Instead, a new report from the CIA says Kim simply wants US businesses, perhaps a burger joint, to open within the country as a gesture of goodwill and an economic carrot, CNBC reports.
Since taking office, Trump has made North Korea a top priority and the toughest sanctions ever on Pyongyang. Additionally, Trump has been credited with getting China, North Korea's biggest ally and trading partner, to participate in the sanctions.
As a result, doing business with North Korea became nearly impossible and its trade deficit with China ballooned.
For a leader that's meant to be seen as the all-powerful resistance to the West, crying about Trump-imposed sanctions would be a big story possibly signalling an about face.