LOS ANGELES — Last month, President-elect Donald Trump entered a sold-out Madison Square Garden to attend the mixed martial arts extravaganza UFC 309. Kid Rock's "American Bad Ass" played and the crowd erupted in cheers, chanting "USA! USA!"

The incoming 47th president was flanked by UFC president Dana White and a cortege of Trumpworld insiders tapped for the new administration, including Elon Musk, Robert F. Kennedy Jr. and Tulsi Gabbard.

Also present was Hollywood mogul Ari Emanuel, head of the Endeavor Group and the CEO of UFC's parent company, TKO.

Inside the arena, Trump approached the Octagon-side "promoters table" where White and UFC commentator Joe Rogan sit and where he was seen briefly chatting with Emanuel.

Their meeting at the UFC bout was the second time the pair had spoken since Trump's 2024 presidential run, said a person close to Emanuel who was not authorized to comment. Emanuel, Trump's former agent, called him last summer after he was shot at a campaign rally to ask how he was doing, and Trump appreciated the call, said the source.

As Hollywood begins to grapple with how to navigate Trumpworld 2.0, few are better positioned to navigate the new administration than Emanuel.

The brash power player has staunch Democratic bona fides: He has hosted fundraisers for the party and donated to a number of its candidates over the years. During this presidential cycle he gave nearly $1 million to Kamala Harris' PAC and campaign. And his brother Rahm was President Obama's first chief of staff, later the mayor of Chicago and Biden's ambassador to Japan.

Nonetheless, Ari Emanuel has cultivated multifaceted ties to Trump and many of his associates over the years, among them Elon Musk, UFC's White and WWE's Vince McMahon. One of William Morris Endeavor's literary agents represented Vice President-elect JD Vance when he sold his 2016 bestselling memoir, "Hillbilly Elegy" (Emanuel interviewed Vance at an employee book club series in 2018 in Cleveland).

Emanuel, who has publicly castigated Israeli prime minister Benjamin Netanyahu and blasted President Biden and his aides for not dropping out of the presidential race earlier, says that he will not be shy about voicing his concerns to Trump, telling The Times, "If I really disagree with something that I think he would do, I will definitely pick up the phone."

'The King of Hollywood'

Back in 2010, Emanuel became Trump's agent, just months after the Hollywood power broker engineered a stunning takeover of the famed William Morris Agency. The New York real estate developer turned reality TV star was hosting "Celebrity Apprentice," and he called Emanuel as he played golf during his firm's annual off-site in Palm Springs.

"Ari, this is Donald Trump. Did you make that Conan deal? I want you to be my agent," Trump told him, according to someone close to Emanuel.

The NBC show was flagging in the ratings — despite Trump insisting otherwise — and he wanted what he always craved: a better deal.

Endeavor had extracted some major concessions from NBC after the network axed Conan O'Brien as host of "The Tonight Show," including a $32.5-million payout.

The deal caught Trump's attention and he wanted the man he'd taken to calling "the King of Hollywood" representing him.

Five years later, Trump announced his first run for president. After he called Mexicans "rapists" who brought drugs and crime into the country, NBC cut ties with him. Trump bought out NBC's interest in the Miss Universe Organization and then sold Miss Universe to Emanuel's Endeavor for an undisclosed sum. In November 2016, Trump was elected the 45th president of the United States.

Although Emanuel has not represented Trump since the latter announced his 2024 candidacy, he was photographed meeting Trump at his golf club in Bedminster, N.J., after the 2016 election. Emanuel has downplayed the visit to those around him.

Three years later, Emanuel's name surfaced in a trove of some 100 documents from Trump's transition that was leaked to the political news site Axios, indicating he had been vetted for an unspecified role in the administration. A spokesperson for Endeavor declined to comment at the time.

Trump, who has called Emanuel "a very good friend of mine," said at the start of his first administration: "Even though he's not political, he's political. He gets it."

Elon Musk: The Trump whisperer

Over the years, Emanuel's relationship with Elon Musk took shape, and its contours deepened as the uber-agent transformed Endeavor from a talent agency into a global sports and entertainment powerhouse. In March 2021, a month before Endeavor went public on the New York Stock Exchange, Musk was tapped to join the company's board (he resigned in 2022).

That same year, Musk was among a clutch of intimates (along with Brian Grazer and Larry David) who attended Emanuel's 60th birthday party at Ivy on the Shore in Santa Monica. In the summer of 2022, when Emanuel married fashion designer Sarah Staudinger, Musk joined a select group of A-listers (Mark Wahlberg, David Zaslav) invited to their wedding in St. Tropez, France. Months later Musk was photographed yachting off the coast of Greece with the newlyweds.

Behind the scenes, Emanuel has played a quiet role in some of Musk's notable businesses.

When Musk attempted to back out of his $44-billion takeover of Twitter in 2022, causing a rift with its board, Emanuel reached out to Egon Durban, a Twitter board member and co-CEO of private equity firm Silver Lake, then Endeavor's largest shareholder.

Emanuel urged the company to "find a solution" to the legal battle ahead of the scheduled trial. Musk and the board ultimately sealed the deal and the billionaire took the social platform private, later renaming it X.

As Emanuel played peace broker between Musk and the Twitter board, he sent Musk a three-paragraph proposal on the encrypted text platform Signal offering to run Twitter with Endeavor for a fee of $100 million, saying he would cut costs, create a better culture and manage relationships with advertisers and marketers.

Emanuel's overture, unearthed in Walter Isaacson's flattering biography of the Tesla mogul, never moved forward.

Jared Birchall, Musk's right-hand man, called it "the most insulting, demeaning, insane message."

The scuttled offer apparently did little to ruffle feathers. In January 2023, Axios revealed that Endeavor had acquired a small stake in X. As for Emanuel, he has been spotted around town driving a glossy black Cybertruck.

Dana White: Trump's strongman champion

In 2016, the same year that Endeavor acquired the Ultimate Fighting Championship (UFC) for more than $4 billion, its president, Dana White, a bombastic former mixed martial arts (MMA) manager, took the stage at the Republican National Convention in Cleveland and gave a fulsome endorsement of the GOP presidential nominee. "I've been in the fight business my whole life," he said, and Trump, he noted, was a "fighter."

Trump had thrown White a lifeline years ago. In 2000, New Jersey legalized MMA and Trump reached out to White offering to hold fights at his now-defunct Trump Taj Mahal casino and hotel in Atlantic City. Trump himself showed up for events, raising UFC's profile.

Since then, White has been one of Trump's staunchest supporters outside of politics. He has invited Trump to UFC events even as Trump faced a spate of criminal, civil and other legal challenges.

As White became known as MAGA's frontman, he and Emanuel forged a successful business partnership turning the UFC into the world's largest MMA promotion.

"Now with Ari, he and I end up being perfect partners together. It's really cool," White told the website MMA Fighting. "You think of a guy like Ari, if you watch 'Entourage' — Ari Emanuel has no ego when he deals in business and he's a f—king killer and I love that about him too."

Emanuel has heaped praise on White too, crediting him with helping to save Endeavor's sprawling empire during the pandemic.

White implemented an aggressive plan to continue to hold fight events on Yas Island in the United Arab Emirates, dubbed "Fight Island."

The Emanuel-White alliance reached its apex last fall when Endeavor officially merged UFC and World Wrestling Entertainment (WWE) into TKO Group Holdings, a publicly traded $21.4-billion fighting sports and entertainment giant.

Vince and Linda McMahon: Trump's fight squad

Emanuel has deep connections with another figure who has close ties to Trump: Vince McMahon.

Last April on CNBC, Emanuel sat next to McMahon and announced the UFC-WWE merger, insisting that McMahon was a driving force and paramount to the deal.

McMahon was named executive chairman of the newly created TKO Group Holdings as a condition of the deal, according to SEC filings.

McMahon boasted that the new company was a "live sports and entertainment powerhouse with a collective fan base of more than a billion people."

Emanuel had a long-standing relationship with McMahon. They met in the late 1990s, soon after Emanuel launched his own talent agency. He convinced McMahon to let Endeavor represent the WWE for endorsement opportunities and media rights.

By then, McMahon had already developed close ties to Trump.

During the 1980s, Trump became a WWE fixture and the two men grew friendly. Trump hosted WrestleMania extravaganzas at his hotels and made numerous appearances at matches. In 2013, Trump was inducted into the WWE's Hall of Fame.

In 2007 and '09, WWE made payments of $4 million and $1 million, respectively, to the Trump Foundation, according to the foundation's tax filings. The foundation was dissolved by court order in 2018 after the New York attorney general found that it had illegally used charitable funds for political purposes.

McMahon exited TKO in January after former WWE employee Janel Grant , sued the company, McMahon and the former head of talent relations alleging sexual assault, trafficking and emotional abuse. This followed previously disclosed revelations that McMahon had paid millions in hush money to multiple women to quash allegations of sexual misconduct between 2006 and 2022. McMahon has denied the accusations of wrongdoing.

The allegations triggered investigations by the Securities and Exchange Commission and the Department of Justice, raising questions as to how or if the Trump DOJ will handle the government probes.

Emanuel has periodically stayed in touch with McMahon, who is no longer involved in the running of TKO and WWE.

The McMahon family appears to be in good standing with Trump.

In 2017, Trump named McMahon's estranged wife, Linda, to run the Small Business Administration. Two years later, she resigned to become chairwoman of America First Action, a pro-Trump super-PAC; more recently, she co-headed his transition team. Last month, Trump nominated McMahon to serve in his cabinet as his education secretary. ___

©2024 Los Angeles Times. Visit at latimes.com. Distributed by Tribune Content Agency, LLC.