The president still nurses the wound of those years and the insults Wynn lobbed at him, according to sources close to Trump. Which means that when Wynn came crawling during the election, singing his former foe’s praises, Trump was eager to kick back and watch the show. They were chummy along the campaign trail during the general election, with Wynn also stumping with Trump’s sons Don Jr. and Eric. “It was always just billionaire ego bullshit,” said one Trump campaign official who witnessed their exchanges. “Like, ‘Haha, my building is a couple feet taller than your building.’ That kind of thing.”

Indeed, Trump was always quick to “tease” Wynn that he “came on late” to the campaign, according to a Republican consultant who has been in several meetings with the two of them. It was as though to remind Wynn that Trump, though content to reopen the lines of communication, wouldn’t be seduced so easily.

Yet far from keeping Wynn at a distance, Trump seemed insistent on tightening their relationship. “They became pretty close,” said former Speaker of the House Newt Gingrich. The Republican consultant said Trump did consider Wynn a “friend,” but it was known that the president took great pleasure in how their roles had reversed. Wynn had once been the catalyst for Trump’s shortfalls in Vegas, and now, when it came to Wynn’s policy priorities, Trump was the one who pulled the strings.

During the transition, Wynn bordered on “sycophantic” in his outreach, according to a former senior White House official, particularly on the topic of China. Careful to punctuate his requests with lavish praise, Wynn, who runs a massive casino operation in Macau, often urged Trump to reconsider his pledge to be “tough on China.” (There’s no evidence that White House actions that affect China—most recently slapping tariffs on solar-panel and washing-machine imports—have been in any way influenced by Wynn. Asked if Wynn had ever used his relationship with Trump to influence China policy, a spokesman for Wynn said, “No, he has not.”)

Wynn then volunteered to arrange entertainment for Trump’s inauguration, to help achieve the aura of “soft sensuality” that the event’s chairman,Tom Barrack, had promised. According to the source who has sat in on meetings with Trump and Wynn, however, it was “a struggle, but it wasn’t Steve’s fault.” Not even Wynn’s extensive rolodex of celebrities could help him nab the artists he wanted most, including Tim McGraw, Faith Hill, and Elton John. “As soon as he’d get close to bringing one on, word would leak out, and they’d immediately deny,” the source said. “Steve got very frustrated. He was clearly upset.”

Which made him wary at first when Trump asked him to take over as finance chair of the RNC. He was already versed in how tenuous the electoral map looked for Republicans in the lead up to 2018. Trump courted him by giving him a tour of the White House, pausing often to ask Wynn—an avid art collector—about certain paintings. “He would ask him what the valuation of all the art was,” said a Republican consultant to whom the exchange was relayed. “You know, that’s Trump, he’s always wanting to know what things are worth.” For his part, the source said, Wynn thought it was “funny.” “I think he found it charming.”