Hong Kong CNN Business  — 

HNA Group was once one of China’s largest conglomerates, spending billions of dollars to expand its reach around the world. Now it could go bankrupt.

The Hainan-based company’s creditors have asked a Chinese court to approve plans for the company to enter bankruptcy, HNA said in a statement Friday. The creditors said the conglomerate couldn’t pay off its debts.

The bankruptcy filing marks a dramatic fall for one of the country’s most prominent companies. HNA began life as an airline but grew rapidly through investments in real estate and finance, and overseas acquisitions, to become one of the most important players in China’s private sector.

Starting in 2015, HNA embarked on a $40 billion shopping spree that included investments in Hilton (HLT) and Deutsche Bank (DB). By the end of 2017, HNA’s assets topped 1.2 trillion yuan ($186 billion).

But those acquisitions were built on a lot of debt, which hit 707 billion yuan ($110 billion) by June 2019. The company’s woes were exacerbated by the coronavirus pandemic, and in February 2020, government officials in Hainan took control. At the request of the company, authorities established a “working group” with other agencies in a bid to solve HNA’s financial crisis.

HNA’s looming bankruptcy is also the latest sign of the demise of some of China’s most aggressive global dealmakers. Anbang Insurance, another major conglomerate that made huge overseas purchases, was seized by Chinese regulators in February 2018. It once owned Waldorf Astoria and Strategic Hotels & Resorts.

Beijing, meanwhile, has been trying to tighten its grip over the country’s private sector. Much of the scrutiny over companies like HNA and Anbang began in 2017, when regulators began more closely looking into their flashy overseas deals, worried about liquidity risks.

In the years since then, Chinese officials have taken other steps to keep private companies in line. The ruling Chinese Communist Party last September, for example, published an unusually frank set of guidelines that call on its members to “educate private businesspeople to weaponize their minds with [Xi’s] socialism ideology.”

Regulators lately have also been looking for ways to crack down on the country’s massive tech industry. Alibaba (BABA) was recently the target of an antitrust investigation and its financial affiliate, Ant Group, has been asked to overhaul its business.