Democrat presidential hopeful Mike Bloomberg once bragged about scoring his 16-year-old daughter dates in multiple Chinese cities while visiting the country on business.

The former New York City mayor, who is under fire for helping suppress news reports critical of China’s communist regime, made the awkward comments while hobnobbing with young “Wall Street traders” at a Boston College alumni dinner in 1999, according to Wired magazine profile.

“My daughter is tall and busty and blonde,” Michael Bloomberg is telling a table of Boston College graduates. “We went to China together. And what’s a 16-year-old going to do on a business trip?” He pops another carefully buttered piece of bread in his mouth. “So I got her dates in every city in China.” Remembering that I’m also at the table, he glares in my direction. “That’s off the record!” he barks. It’s typical Mike Bloomberg, wanting to have it both ways: imperious man of the people, coarse billionaire, earthy business leader, accessible control freak.

At the time of the dinner, Bloomberg was first emerging on the political stage as a contender to replace then-term limited New York City Mayor Rudy Giuliani. Even though Bloomberg would succeed in his quest for the mayoralty, eventually serving three terms in city hall, his 1999 comments foreshadowed a businesslike approach to the U.S.-China relationship.

As mayor, Bloomberg often championed policies that seemed copied right out of Beijing’s playbook. For instance, the Bloomberg administration in 2012 sought to ban the use of baby formula in hospitals across New York City, arguing breast feeding was a better alternative. The policy, like many of Bloomberg’s other health initiatives, was modeled off steps the Chinese regime took to promote breast feeding after its food safety protocols were called into question by a 2008 scandal involving infant formula being adulterated with melamine—a compound used when manufacturing plastic.

Bans on baby formula, however, was not the only public issue on which Bloomberg looked to China for cues. When it came to public housing and crime control, the mayor, wittingly or unwittingly, supported policies Beijing relied upon to disenfranchise its large Uyghur population. In particular, Bloomberg proposed during his final months in office that New York City begin fingerprinting public housing recipients to curb crime. The proposal mirrors, although on a much smaller scale, actions the Chinese government took when first cracking down on Uyghurs in the early 2010s.

Bloomberg’s ties to China did not just stop in public life, but extended to the dealings of his company, Bloomberg LP, as well. In 2013, the company was accused of pressuring its media subsidiary, Bloomberg News, to kill stories about the alleged political corruption swirling around the family of China’s president, Xi Jinping. Bloomberg LP allegedly tried to silence the reporters working on such stories through strict enforcement of non disclosure agreements. The purported intimidation, which has resurfaced in recent days, led to the resignation of several high-ranking reporters and editors in protest.

Even though Bloomberg LP has denied suppressing stories about China’s communist brass, the former mayor did admit in 2014 that his news division hews closely to the country’s sedition laws.

“In China, they have rules about what you can publish,” Bloomberg told CNBC at the time. “We follow those rules. If you don’t follow the rules, you’re not in the country.”

More troubling is that around the same time that Bloomberg News was reportedly being forced to squash stories, the former mayor was plotting a broader investment in China. In recent years, Bloomberg LP has launched efforts to make it easier for U.S. companies to conduct transactions in Chinese currency. Such undertakings have ensured mainland China and Hong Kong account for nearly five percent of Bloomberg LP’s annual revenue.

As many have noted, Bloomberg’s private and public history with China casts a shadow not only over his position on trade, but also his recent refusal to call out Xi Jinping for his autocratic tendencies.

“Xi Jinping is not a dictator,” the former mayor told PBS’s Margaret Hoover during an interview in September 2019. “He has to satisfy his constituents, or he’s not going to survive.”