In the final weeks of the presidential campaign, Democrats were desperate to obtain and release tapes from the archives of Donald Trump’s reality-TV show The Apprentice. There was a similar scramble conducted in the final 10 days of the campaign that was not revealed publicly at the time: a search for tapes from the Miss Universe Organization archives, which, until last year, Trump owned.

According to four sources, Donald Trump’s longtime friend and former agent Ari Emanuel declined appeals from powerful Democrats to release tapes filmed while Trump owned the Miss Universe Organization (which also owns the Miss USA and Miss Teen USA pageants). The Daily Beast spoke to more than a dozen people for this story, including former and current WME-IMG clients, Clinton and Obama campaign insiders, and former Miss Universe Organization employees. The sources spoke only on the condition of anonymity given Emanuel’s vast influence in the entertainment industry and his penchant for holding grudges.

Emanuel, 55, is a powerhouse talent agent who is notorious in the entertainment business for his aggressive, hard-charging negotiating style. His lineage is also legendary—he is the brother of Ezekiel, or “Zeke,” a renowned oncologist and one of the architects of Obamacare, and Rahm, the former White House chief of staff and current mayor of Chicago.

Ari Emanuel, through the company of which he is co-CEO, WME-IMG, bought 100 percent of the Miss Universe Organization from Trump in 2015; but he refused requests to release or even look into what tapes were held in the archives just days before the Nov. 8 election. At one point, sources tell The Daily Beast, the Miss Universe archives contained audio and video that could have damaged Trump’s prospects in the presidential race.

The revelation that Emanuel didn’t want to look into what might be in the Miss Universe Organization archives isn’t the only way some feel he aided Trump. Emanuel has been an active and vocal Democrat in the past, using his checkbook, fundraising network, and bully pulpit to advocate for his candidates of choice, but was silent in the general election, neither defending or fundraising for Hillary Clinton nor speaking out against Trump.

Twelve days after the election, as Trump was meeting with potential Cabinet picks at his golf course in Bedminster, New Jersey, Emanuel also showed up to meet with Trump and Vice President-elect Mike Pence, raising eyebrows on the left coast. Many were surprised to see the liberal Obama-loving Hollywood agent meeting with Trump, especially given the fact that he wasn’t in line for an appointment.

But for those who work in the entertainment industry, Emanuel and Trump’s meeting was no surprise, as they’ve long been friends and Emanuel represented Trump for many years. In fact, their relationship, and Emanuel’s unwillingness to publicly attack Trump, was often a source of great frustration over the past 18 months for Emanuel’s allies and enemies alike, three sources tell The Daily Beast.

Emanuel, aware of the controversy his visit with Trump would cause, dispatched some of the talent agents at WME-IMG to text-message clients to let them know that the meeting would be taking place. They told the clients, according to two sources, that the meeting was intended to share concerns and take Trump to task. And that’s just how Emanuel’s allies frame the meeting. But according to a key Trump transition source, that is not what took place. While Emanuel did offer counsel to Trump, and certainly pushed his progressive views, his advice was related to being more effective as president, not taking Trump to task for what many believe are racist and sexist statements. The source says Emanuel, who is known for his use of colorful, unfiltered language, did not hold Trump’s feet to the fire in the way that some would expect.

In interviews, Trump has said he and Emanuel speak often by phone. One source told The Daily Beast that they speak as often as once a week. While Emanuel no longer represents Trump, he helped the former reality-TV star negotiate some of his key deals around the NBC competition program The Apprentice, and last year, WME-IMG bought the Miss Universe Pageant competition from Trump for an undisclosed sum. (In a tweet, Trump said it was a “record” price.)

During the course of the campaign, Emanuel kept a comfortable distance from Trump while never denouncing him publicly. In an interview with Michael Wolff for The Hollywood Reporter, Trump said, “He’s a very good friend of mine. He calls me a lot. I call him a lot and we talk. He’s very political. Even though he’s not political, he’s political. He gets it.”

Trump told Wolff that Emanuel had even offered to put together a film for the Republican convention. Two sources say that when some clients learned of this alleged commitment they contacted WME-IMG to protest, which forced Emanuel to say publicly that he had made no such offer to Trump.

The search for the elusive Miss Universe Organization tapes started after the Associated Press published a story alleging that Trump would frequently use lewd language on the set of The Apprentice. That led producers at the entertainment news program Access Hollywood, which is owned by NBC, to scour their tape archives. During that hunt, they discovered the now-infamous Trump hot-mic tape.

That weekend, public pressure started to build on Apprentice producer Mark Burnett to release any newsworthy tapes of Trump. In a joint statement, Burnett and MGM said Burnett did not have the right to release any footage, as he had sold his production company, and his share of the Apprentice rights, to MGM TV. A New York Times report said Trump may also have veto power over whether to release Apprentice footage. Under increasing pressure to denounce Trump, Burnett released a statement saying, “I am not now and have never been a supporter of Donald Trump’s candidacy. I am NOT ‘Pro-Trump.’ Further, my wife and I reject the hatred, division, and misogyny that has been a very unfortunate part of his campaign.”

In Dallas, billionaire businessman Mark Cuban, the owner of the Dallas Mavericks and co-host of ABC’s Shark Tank, was hearing from people that there were controversial tapes in the Miss Universe Organization archives. By that time, several pageant contestants had come out and said Trump had a penchant for going backstage and barging into the dressing areas, and that was backed up by Trump’s own words.

CNN’s KFILE was the first to uncover an old interview Trump had with Howard Stern in which he bragged that he would go backstage and aligned that ability with his ownership of the pageant: “You know, no men are anywhere. And I’m allowed to go in because I’m the owner of the pageant. And therefore I’m inspecting it… Is everyone OK? You know, they’re standing there with no clothes. And you see these incredible-looking women. And so I sort of get away with things like that.”

And in 2009, TMZ obtained an audio tape of Trump talking to Miss USA contestants before the pageant and asking them to pick another contestant they deemed to be attractive. This resulted in what former Miss USA Carrie Prejean referred to a “rejects line” in her autobiography. Prejean also said some of the women who were not picked as attractive by their fellow contestants ended up sobbing backstage.

Three sources confirmed to The Daily Beast that politically controversial tapes did exist within the Miss Universe Organization archives at one point. It is unclear if those tapes have been destroyed since WME-IMG bought the Miss Universe Organization. According to the sources, the tapes (and the accompanying audio) were not part of the actual pageants, rather they involved backstage, behind-the-scenes filming for social media and other promotional purposes.

According to four sources, attempts were made by Trump opponents to contact editors and production staff who used to work for the Miss Universe Organization, but they were unresponsive. It’s important to note that the non-disclosure agreements that the Trump Organization requires all of its staff to sign are legendarily tough, leading many to stay silent out of fear of being sued by the famously litigious Trump.

Cuban, who is represented by WME-IMG, then reached out to his agent to inquire about the tapes and push for them to be released. His agent spoke to Emanuel, who according to three sources came back with a terse reply: “My brother is in politics, I’m not.” In an interview earlier this year with The Hollywood Reporter, Emanuel used the same line when he was asked if he would be taking Trump back as a client given his campaign’s rhetoric.

Clinton allies then reached out to a powerful figure in Emanuel’s universe: co-founder of Silverlake Partners Glenn Hutchins. Silverlake is the private-equity firm that bought a big chunk of what was then WME in 2012 (it did not acquire IMG until 2013). Hutchins did not want to get in the middle of the battle, according to sources.

Hutchins, through a spokesman, declined to comment. Cuban also declined to comment.

These rejections left the sources shocked and exasperated, with one saying, “The public had a right to see these tapes or hear the audio. He’s juggling with everyone else’s future because of loyalty to Trump?”

Three sources confirmed to The Daily Beast that Emanuel never said that embarrassing tapes didn’t exist or that he had scoured the archives to be sure. His message was clear: “Get over it, move on,” as one source framed Emanuel’s pushback.

Through a WME-IMG spokesman, Emanuel declined to comment.

No one believes that Emanuel is a closet conservative. His decision not to dig deeper on the Miss Universe matter appears to be driven by a distrust of Clinton and a pragmatic look at the business opportunities available to him and WME-IMG should he stay tight-lipped. For example, WME-IMG owns the Ultimate Fighting Championship (UFC) and the Professional Bull Riders, and both of these sports have audiences that skew conservative.

When Emanuel’s friends and business associates would bring up concerns about a possible Trump victory, he would often wave them away, explaining that Trump’s talk on the campaign trail was just the rhetoric that would help him win and that he was going to be much more moderate in practice. One major television executive producer, who is a client of WME-IMG, is livid about what he calls the “bill of goods” he was sold about Trump not being as conservative when he actually governs. “He promised a moderate Trump and I tended to believe him,” this person said. “I always knew that he was putting on a show to get votes, but now I get Mike Pence? I get Jeff Sessions? My kid has to deal with an educational system run by Betsy DeVos? Ari is as much a fucking snake-oil salesman as Trump.”

If Emanuel has a soft spot for Trump, with respect to Clinton his feelings appear to be the opposite. He has been a generous donor to Obama and other Democratic committees over the past decade, contributing hundreds of thousands of dollars, according to Federal Election Commission records. But when it came to Clinton, Emanuel’s checkbook and Rolodex remained closed in 2016. Emanuel gave one check—just one month after Clinton announced her candidacy in April 2015—for $2,700, which was given through a fundraiser hosted by longtime Clinton friend and donor Haim Saban, a source with knowledge of the contribution confirmed. Emanuel did not engage his prodigious fundraising network either. He didn’t bundle money for Clinton as he did for both Obama campaigns, and WME employees (there are 6,000, according to Emanuel) contributed $91,000 to Clinton—a far cry from campaigns in years past. One source described the process of getting a WME-IMG agent to contribute to Clinton as “torture.”

Sources close to Emanuel claim that he was not asked to actively engage in the Clinton campaign on a financial basis and that he offered to help with her social-media efforts but his offer was rejected. But sources with knowledge of the outreach to Emanuel push back on that claim. Emanuel was repeatedly engaged by Saban, and according to several sources, he told Saban that he would get more involved in the general election (which he did not). And several Clinton campaign sources claim that they never heard about Emanuel offering to help with social media.

But what was most surprising was to learn that an advertising firm that WME-IMG owns 50 percent of, Droga5, produced some of Clinton’s ads in the presidential race. (According to federal election records, it collected over $300,000 in fees.) Emanuel’s association with Droga5 was shocking to Clinton campaign sources, with one texting “WTF” in response to the information. The revelation that Emanuel may have profited off the Clinton campaign without actively supporting her candidacy angered Clinton allies.

So what does Ari Emanuel have against Hillary Clinton? Back in 2008, he wrote two harsh blog posts for the website of another client: Arianna Huffington.

In one post, headlined “The Curious Math of Hillary’s ‘35 Years of Experience,’” Emanuel questioned her claim in 2008 that she had 35 years of experience as a change agent. In another post, headlined “What Hillary Really Learned in the White House,” Emanuel wrote, “The real experience Hillary Clinton gained during her years in the White House has finally been revealed: She learned, just like her husband, how to manipulate words to cover up her lies.”

Those who have known Emanuel for years, while understanding his apparently intense dislike of Clinton and loyalty to Trump, were confused by Emanuel’s silence and lack of action for the Democratic nominee, with one saying, “Trump goes against everything Ari has believed in: his obsession with climate-change activism and passion for racial and religious equality.”

In 2004, when Emanuel’s client Michael Moore was in a dispute with Disney over the release of his anti-Bush documentary Fahrenheit 9/11, Emanuel went public with a revelation that caused a firestorm. Emanuel told The New York Times that then-Disney CEO Michael Eisner told him he didn’t want to release the film because he was worried that tax breaks the company received from the state of Florida, where President Bush’s brother Jeb was governor, would be endangered. Disney executives denied this accusation, but the moment serves as a perfect example of what Emanuel is eminently capable of: speaking truth to power.

But it was another Huffington Post blog post by Emanuel that may leave some more confused about why he didn’t speak out against Trump. In 2006, Mel Gibson made anti-Semitic statements after being arrested in Malibu for drunk driving, and the news shocked many in the entertainment industry. Emanuel was famously unforgiving in his reaction.

In a blog post, he wrote, “At a time of escalating tensions in the world, the entertainment industry cannot idly stand by and allow Mel Gibson to get away with such tragically inflammatory statements.” Emanuel declared that everyone in the entertainment industry needed to recognize the import of “professionally shunning Mel Gibson and refusing to work with him, even if it means a sacrifice to their bottom line.” He added, “There are times in history when standing up against bigotry and racism is more important than money.”

Ten years later, Emanuel was silent. This time, his silence wasn’t reserved for a Hollywood actor but the next leader of the free world.

Follow Yashar on Twitter: @Yashar