Last October, Bob Iger donned shades and a ceremonial black robe to help choose the finalists for the Disney employees’ Halloween costume contest. It was a warm day on the studio lot in Burbank, California, and the CEO’s top lieutenants joined him to help with the judging. A George Lucas look-alike paraded by, which made Iger smile, then a merry Mary Poppins. But it had been a painful year at the Magic Kingdom, and the group representing Disneyland’s Haunted Mansion tilted a little dark. One of them hoisted a sign with a hatchet, dripping blood, a picture of Iger altered so he was smiling like Jack Nicholson in The Shining and the words, “I’m BaaaCK!! 4 DAYS A WEEK BABY!!” The hatchet was presumably a symbol for cuts and layoffs, the creepy prose a reference to Iger’s unpopular return-to-work policy. “The vibe has been tough,” one Disney employee told us earlier this year. “They really put us through the wringer.”

In November 2022, Iger made a surprise return to Disney following a much-heralded (and very brief) retirement to clean up the messes created by his handpicked successor, Bob Chapek, and deal with a radically altered entertainment landscape. Within a year, he eliminated 8,000 positions as part of a $7.5 billion cost cutting plan. Several of the company’s recent sequels, live-action remakes, and IP efforts had disappointed at the box office. Wall Street was pressuring him to make Disney+ profitable. The debilitating actors and writers strikes were underway. And billionaire activist investor Nelson Peltz was threatening an assault on the Magic Kingdom. The CEO’s latest contract is set to expire at the end of 2026, after he turns 75, and some of the lieutenants who helped him judge the costume contest are now in the running to be America’s next top Iger.

Iger has always been clear: He loves running Disney. But if he was reluctant to retire in the past, he doesn’t appear to be now. By many accounts, the succession question is now a top priority as he and the Disney board narrow in on a handful of internal candidates and consider potential external candidates. The board essentially rubber-stamped Iger’s last choice. It won’t this time. “Bob Chapek may be the biggest mistake Bob Iger made in his career,” says Bank of America analyst Jessica Reif Ehrlich. A source with close ties to Disney puts it more colorfully: “The board royally fucked up last time.”

Disney’s board is now stacked with executives who handled their own smooth handoffs. A source familiar with the process says the company won’t make a decision this year. Ideally, it will in 2025 so Iger can bring the CEO in waiting up to speed and show them Disney’s version of the nuclear codes. It’s said that there are now four key internal candidates, who have to figure out how to lobby for the job without looking like they’re lobbying for the job: Disney Entertainment cochairmen Dana Walden and Alan Bergman, ESPN chairman Jimmy Pitaro, and Disney Experiences chairman Josh D’Amaro. There’s also a massive Disney workforce treading on the tippiest of toes. “People don’t know which horse to bet on,” says the source with close ties. “They’re afraid to cross anybody.”

Anyone who thinks Succession was entirely about the Murdochs hasn’t spent much time studying Disney. Michael Eisner, who preceded Iger as CEO, left the company after a shareholder revolt. Eisner was a charming but capricious executive who hadn’t always been convinced Iger was ideal for the job. Iger had joined Disney in 1996, following its acquisition of Capital Cities/ABC, having worked his way up from weatherman at a small cable station to top TV exec. Here’s the with-friends-like-these memo Eisner wrote confidants on the board about Iger when he was mulling potential replacements years before his departure: “He is not an enlightened or brilliantly creative man, but with a strong board he absolutely could do the job.”

Once Iger had the gig, he also found it hard to relinquish. After extending his contract several times, he set up a bake-off between two of his top lieutenants with an eye toward succession. Later, Iger reportedly lost confidence in the winning baker, who quickly left the company. Iger’s contract was extended again in 2017. “I’m serious about it this time,” he told an audience, meaning his retirement as CEO. Later that year, Disney announced a deal ultimately worth more than $70 billion to acquire the lion’s share of 21st Century Fox’s film and TV assets and re-upped his contract again. Though he finally stepped down as CEO in 2020, he didn’t even truly retire, instead becoming executive chairman for another 22 months. Chapek took over right in time for the devastating pandemic—and his relationship with Iger reportedly disintegrated. He didn’t last three years in the role.

After Iger returned as CEO, the board tacked an extra two years onto his new contract to give him enough time to get succession right. Disney is the second biggest entertainment company in the world, after Netflix. It’s worth more than $200 billion and has swallowed, among other things, Lucasfilm, Marvel, and most of Fox. It operates more like a small country (population: 225,000) than your average entertainment conglomerate. Many of its workers—or cast members as they’re earnestly called in the parks division—are loyal to the company in a way that borders on nationalism. Who could possibly oversee it all?

One Disney employee characterizes the race as “an open ball game,” but most Hollywood insiders believe that it’s Walden’s job to lose. “The word about succession is that it’s all Dana all the time,” says a top agent. Walden, 59, is a longtime TV executive with a Svengali-​like ability to woo talent. She also has a close relationship with Iger, her neighbor in tony Brentwood, where they regularly stroll among the mansions. Walden’s three-decade-long career in television likely reminds Iger of his own path to the top, even if that means she might have blind spots when it comes to the theme parks or the ESPN business. A former Disney executive who worked closely with Walden says, “I think she could be great, but it’s not going to be a slam dunk.”

Others, meanwhile, are convinced that D’Amaro, 53, will take the throne. When he travels to the theme parks, people line up to meet him. Tall and silver-haired, D’Amaro is the executive who seems most built in Iger’s mold, able to charm hourly workers and visiting dignitaries in equal measure. In Hollywood, however, he’s a relative unknown. “Josh has a very Iger-like cult of personality,” says another former Disney executive. “Does he understand how to operate a media business though? Especially a media business that is dealing with the onset of AI and all these other threats to the business? I don’t know.”

Pitaro, 54, and Bergman, 58, are less obvious choices for CEO, though there’s still time. The former is well-liked and has a background running Disney Interactive that gives him perspective on how to position Disney for a streaming future. But he’s got his hands full launching the flagship ESPN streaming service and a sports streaming joint venture. As for Bergman, he’s a veteran finance executive who assumed sole control of Disney’s film business two years ago. He’s now focused on reenergizing the movie slate after an uneven few years for Pixar, Marvel, and Lucasfilm.

Disney employees, to their credit, can be as tight-lipped as the Secret Service. Iger and the executives in contention to replace him did not comment for this story, but a spokesman sent a statement, which read in part: “The Disney Board is engaged in a robust and thorough succession planning process to identify Disney’s next CEO and there are currently no designated frontrunners among the very strong candidates being considered, despite any uninformed speculation to the contrary.” Interviews with more than 40 sources, both inside Disney and out, paint a picture of a beloved brand that has a chance to set Hollywood’s course for years to come if it can just settle on the right captain.

On November 20, 2022, Walden stopped by the American Music Awards, which ABC was broadcasting from Downtown LA, then hurried to Dodger Stadium for Elton John’s farewell tour, which Disney+ live streamed. As if that weren’t enough excitement for one evening, an email hit every Disney inbox that night: Iger was coming back. When staffers got the announcement, some were momentarily confused—“We thought we’d clicked on an old email,” recalls an executive—and then they were elated. Less than three years earlier, Iger had handed the CEO reins to Chapek, a Disney veteran who had shepherded the theme park and consumer products businesses to new heights. Now Chapek was out, and Iger—who’d been sporting a salt-and-pepper retirement beard and boasting about his carefree new life—was returning for a second stint leading the company.

The years that Chapek ran the company were rough on morale. Yes, the pandemic was a nightmare that decimated theme parks and movie theaters overnight. But Chapek, a hard-nosed number cruncher from Indiana, made some profound PR gaffes, like the poor handling of a lawsuit brought by Scarlett Johansson over the streaming release of Black Widow and his initially out-of-touch response to Florida’s “Don’t Say Gay” bill, which eroded trust with Disney’s progressive employee base. (Chapek changed course on the latter.) When Iger returned, Disney’s stock surged. The man who’d overseen one of the most prosperous periods in Disney history was once again in charge of Mickey, Buzz Lightyear, Iron Man, and Han Solo. “We were all relieved,” an executive says.

Walden had a particularly good reason to celebrate. Under Chapek, creative executives had been stripped of financial decision-making authority. Iger restored it. He also handed significantly more power over streaming to Walden, film chief Bergman, and ESPN’s Pitaro. For Hollywood, it seemed like a sign that they were being set up as potential successors. It had been a remarkable rise for Walden, whom Iger tapped to come aboard Disney after acquiring most of Fox in 2019. She now oversees a broad portfolio that includes ABC, FX, Freeform, and the Disney Channel, which she is managing as the traditional TV business declines. The Bear has been a surprise awards juggernaut. Abbott Elementary has set records for ABC and brought broadcast TV back into the conversation. Walden is a highly visible force in Hollywood. Now she needs to produce hits for Disney+ while reining in costs.

Walden started at Fox as a publicist in the 1990s. When she moved into programming, she demonstrated an uncanny understanding of the zeitgeist. Modern Family, 24, Glee—she had a hand in making them all hits. About a decade ago, she and her partner running Fox had dinner with Dan Fogelman, a screenwriter on Disney kids classics Cars and Tangled, during a fallow period in his career. Fogelman recalls her saying, “I’m ready to make a bet on you. I want to give you the environment where you’re nurtured and protected and where the right decisions are made to support you.” Not long after, he turned in a script for a family drama called This Is Us. It became the number one new show on TV in the 18-to-49 demographic and ran for six seasons. “She just completely held up her end of the bargain,” says Fogelman. “She really is part guru, part decision-maker. This business needs more decision-makers who have firm points of view and are not afraid to state them.”

People who worked for Walden at Fox say she could be a challenging boss, though it should be noted that the company encouraged scrappy, entrepreneurial hustle—and that women leaders in Hollywood are often subjected to more scrutiny than their male counterparts. “She had a spidey sense for everybody’s vulnerabilities and went right at ’em,” says a former employee. “If you were doing a great job, sometimes she would praise you, but oftentimes she would make you feel terrible to keep you off-balance and to make you work even harder.” Some say Walden’s edges have softened at Disney.

Kelly Ripa says it was Walden’s idea to make Ripa’s husband, Mark Consuelos, her cohost on Live, adding that “it was the first smooth transition that I’ve experienced” in 20-plus years. Grey’s Anatomy icon Ellen Pompeo credits Walden with helping keep her at Disney. “Dana was a huge part of me continuing on in this role,” she says. “She’s a strong leader who values talent relationships and has found ways to keep me at Disney, to let me grow and feel creative.” Many people would follow Walden to the ends of the earth. “There is something very charismatic about her,” says the former employee. “You felt like you were working for somebody who was really smart, almost clairvoyant.”

Many of Walden’s closest friends are people who used to work for her, or still do. Ryan Murphy met her in the early 2000s and with her support went on to make Glee for Fox. She is now the godmother of his three sons, and when one of them was diagnosed with cancer as a baby, she helped him get into the best hospital for treatment. During those panicky early days of COVID, when Fogelman thought his newborn son might have been infected, Walden worked the phones to get advice from doctors. “Dana is the person everyone in town calls in the event of an emergency,” says Murphy.

Disney has never been led by a woman. Even the source close to Disney, who points out that Walden doesn’t have as much financial experience as some of the other candidates, says, “From an entertainment and creative perspective, Dana would be a fantastic choice—and a historic choice.”

Last July, Disney held a premiere for its Haunted Mansion movie at Disneyland in Anaheim, California. SAG-AFTRA members had just gone on strike, so none of the stars were on hand to walk the red carpet. Mickey, Minnie, and Cruella de Vil posed for photos with fans instead. Bergman, who runs the film side of the entertainment business, was having a bumpy summer.

Barbie and Oppenheimer became a two-headed phenomenon for Warner Bros. and Universal, but Disney’s attempt at a blockbuster, Indiana Jones and the Dial of Destiny, failed to meet expectations. Haunted Mansion fared poorly. Even The Little Mermaid underperformed in theaters, forcing Disney to contend with racist critiques about casting Black actor Halle Bailey as Ariel.

Disney is a many-tentacled enterprise, but its success begins and ends with the film studios. That’s where characters are born and, if destiny smiles, become plush toys or theme park rides. Bergman has been at the studio for 23 years. Until longtime film executive Alan Horn retired in 2021, though, he always reported to or worked closely with an executive with deep creative experience. Bergman came from the world of finance, which is certainly an asset. “If you threw up a spreadsheet, he’d absorb it in 30 seconds and send questions back at you, so you better be tight on the numbers,” says an executive who worked with him.

Bergman is often considered a more business-oriented executive, but Horn says he spent a lot of his career learning the creative side of running a film studio. “During my 10 years, I invited him to every single script meeting, every cut of a movie, every interaction I had with creative leaders, and he came to every single one,” he says. “I haven’t seen his SATs or anything, but this guy’s a very smart guy. So I know that he listened. Why did he listen? Because it was important to him to learn the creative side.” When Horn let his friend Iger know that he planned to retire, he told him that Bergman could do the job.

Bergman, who owns a Napa Valley vineyard with his family, is said to be fond of classic Disney IP, and sources say his love for the brand runs deep. He presides over a large portfolio, including animated films, blockbusters, and smaller prestige movies like Poor Things. James Cameron didn’t know Bergman well when he began making the Avatar sequel for Disney but says he grew comfortable with him after test screenings suggested there was still work to be done: “We emerged out of that process with a greater sense of respect for each other than I’ve personally ever felt before working with a studio. It was very contentious with 20th Century Fox and Paramount on Titanic, it was contentious with 20th Century Fox on the first Avatar film, and I didn’t experience any of that with Alan.”

Picking a new CEO is not a personality contest, at least not entirely. But for what it’s worth, multiple sources say that Bergman is old-school and can be prickly and impatient. He’s not considered the likeliest candidate for the CEO job, but fixing a film studio doesn’t leave much time to audition for a new gig. Bergman, of course, isn’t the only movie executive contending with fallout from the pandemic. If Disney’s upcoming slate—Inside Out 2, Deadpool & Wolverine, and Moana 2—scores at the box office, Iger and the board will certainly notice.

As the historic dual strikes stretched into fall last year, things looked dire for every traditional Hollywood studio. Iger invested in an unaffected part of the company: theme parks. In September, Disney announced that it would double its spending, from nearly $30 billion to roughly $60 billion, to expand the parks and cruise lines. Disneyland Resort, for one, could get new shops, restaurants, and rides based on Avatar, Frozen, and Zootopia.

From the Archive: Once Upon a Time in Burbank

The investment was a clear vote of confidence in D’Amaro, who has spent much of his 26-year Disney career working his way through the parks business. Polished and professional, he once moved to Hong Kong Disneyland for four years to rebuild relationships with partners in the region after a rocky launch. He also oversaw Disneyland’s Star Wars: Galaxy’s Edge and spearheaded the parks’ response to the COVID-19 pandemic. Multiple people tell us that no problem is too small for him, even as his responsibilities have grown. Years ago, when D’Amaro was still an up-and-coming executive, he gave Avatar producer Jon Landau a tour of Disney World as they were preparing to bring Pandora to the park. “We are walking around the park for the first time, and I see him stop behind us,” Landau says. “He uses a little cane he has and he picks up some garbage that was on the ground, puts it in the trash bin, and continues on. I thought that was so great. That’s the attention to detail that Josh puts into something.”

D’Amaro seems private about his family life. Of Iger’s top lieutenants, he’s the only one with a prominent public Instagram account—he has 151,000 followers—but it’s entirely devoted to his job. An executive who has worked with him says he’s more image conscious than he lets on: “That effortless cool, there’s effort behind it.” D’Amaro lives with his wife in Orange County, has college-age children, and quietly travels in rarefied circles. During the pandemic he and Delta CEO Ed Bastian worked to revitalize the hospitality industry as members of the U.S. Travel Association. Salesforce CEO Marc Benioff, who counts Disney as one of his company’s key clients, considers D’Amaro a friend and shares his love of Foo Fighters. “He’s somebody who bleeds Disney,” Benioff says. “His heart and soul is very much wrapped up inside the Magic Kingdom.”

Though he’s a parks guy, D’Amaro certainly isn’t Chapek 2.0. It’s not easy to win the loyalty of hourly workers who sometimes feel marginalized at a company Disney’s size, but D’Amaro has navigated that adeptly. (That could come in handy: Performers at Disneyland are now unionizing.) The former colleague calls him a “nice guy to have a drink with,” though he adds that, as a manager, D’Amaro prefers being good cop rather than bad cop. Though he’s never worked at Disney’s film or TV studios, D’Amaro has established relationships with creative executives like Marvel’s Kevin Feige and Disney Animation’s Jennifer Lee as he brings their IP to the parks. “Josh’s got a wealth of experience that often doesn’t get talked about,” says Jim MacPhee, who worked with D’Amaro in the parks. “Just because he has not had the title ‘president of ABC’ doesn’t mean he’s not capable.”

D’Amaro recently worked with Iger to spearhead Disney’s $1.5 billion investment in Epic Games, the company behind the video game phenomenon Fortnite. The deal includes plans to build a virtual universe with Disney characters for players to explore. The announcement of the deal comes at a good time for Disney. Just as the company emerged from the strikes late last year, Peltz, the billionaire investor, shot another arrow in his battle to exert influence over the company.

Peltz was pushing for two seats on the Disney board and came armed with more than $3 billion in Disney shares largely owned by Ike Perlmutter, the disgruntled former Marvel chairman who sold the company to Disney in 2009, only to be quickly sidelined. “Disney has woefully underperformed its peers and its potential,” Peltz’s firm, Trian Partners, said in a statement that pointed to what it saw as Disney’s relatively lackluster stock, falling earnings-per-share, disappointing studio content—and lack of an orderly succession plan.

One of Disney’s counterattacks against Peltz involved unfurling some flashy announcements about ESPN. Days before most of the sports media world gathered in Las Vegas to watch the Chiefs take on the 49ers in the Super Bowl, news came that ESPN was teaming up with rivals at Fox and Warner Bros. Discovery to create a jumbo sports streaming service full of live NFL and NBA games and more.

Pitaro assumed leadership of ESPN six years ago, but this year will define his legacy. He’d been working on the massive streaming project for months as part of his quest to reshape the beleaguered sports media giant for an era when Amazon’s Prime Video streams Thursday Night Football. Disney had more big news to drop: ESPN’s sports programming would be on a stand-alone streaming service by fall of 2025.

Live sports is one of the only ratings bets left, but ESPN has been squeezed by the high price tag for sports rights as the cable TV business withers. People who worked there during the salad days say it’s been painful to watch. “ESPN was a sort of golden child, and you could make the argument that its cash flow helped pay for some tremendous additions to the company, whether it’s Star Wars or Marvel or theme park rides,” says a former employee. “I’m sure it’s been a uniquely difficult time for everybody there.”

Pitaro is a former college football player and an avid Yankees fan. He led Yahoo’s media division before his friend Sheryl Sandberg, then a Disney board member, introduced him to Iger. In 2017, while Pitaro was running Disney Consumer Products and Interactive Media, ESPN’s charismatic leader, John Skipper, abruptly resigned, later revealing that he had a cocaine problem and was the target of an extortion attempt. Pitaro’s love of sports helped him land the job.

You can often find Pitaro eating among his employees in the cafeteria at ESPN’s sprawling Bristol, Connecticut, headquarters. “He’s not somebody who has a giant ego,” says Michael Levine, cohead of CAA Sports, who was fraternity brothers with him at Cornell. “Part of the reason he’s had so much success at the Walt Disney Company and in business is that he’s very solution-oriented.” Pitaro, who’s married to Top Gun: Maverick actor Jean Louisa Kelly, may not be based in Hollywood, but he’s good with talent. He’s been on Iger’s leadership team the longest and, of the top candidates, has worked in the most Disney fiefdoms. Still, by the time his biggest swings pay off, it may be too late for him to get the CEO job. He has certainly made a mark on ESPN already, shoring up relationships with the NFL and MLB and moving the company into the lucrative sports-betting space.

Some question whether Pitaro is ready to succeed Iger, but virtually no one has a negative word to say about the guy. “The six floors of the Team Disney building is a snake pit, but he’s the best human being bar none,” says a former executive.

As the end of 2023 neared, Iger seemed to have finally settled back into running Disney. “I feel that we’ve just emerged from a period of a lot of fixing to one of building again, and I can tell you building is a lot more fun than fixing,” he said at an employee town hall. A few months later, in February, Disney reported that earnings were up, entertainment streaming losses had shrunk to $138 million, and domestic parks and experiences had delivered nearly $6.3 billion in revenue. The company also announced there’d be a $3 billion stock buyback plan that would put money into the pockets of Disney’s shareholders.

Even Iger’s biggest antagonist during the strikes, SAG-AFTRA president Fran Drescher, has eased off. “When you live the life that he gets to live because of his position and power, you become desensitized to what the optics are and how the average worker is going to perceive something,” she told Vanity Fair after the actors strike ended. “I’m sure that if I wasn’t in opposition to him through this and I just met him at a cocktail party, I would think that he was a very lovely and charming man.”

On April 3, Iger ended Peltz’s siege on the boardroom. The investor’s push for seats had lasted over a year, and he and Disney had sometimes traded jabs every few days. Peltz questioned Iger’s leadership and made remarks right out of the Ron DeSantis playbook: “Why do I have to have a Marvel that’s all women? Not that I have anything against women, but why do I have to do that? Why can’t I have Marvels that are both? Why do I need an all-Black cast?” Disney called Peltz’s proxy fight a vanity play for someone with no media or entertainment experience.

In the end, the Disney family (including Iger critic Abigail Disney) and George Lucas urged shareholders to vote with Disney. “Creating magic is not for amateurs,” Lucas said in a statement. But one of Peltz’s allies, the influential advisory firm Institutional Shareholder Services, got in a good shot at Disney for its previously lame game of thrones: “Given the major missteps and severe consequences of the failed 2020 succession, particularly for a company that already had a history of succession drama, it may be difficult for others to simply trust that the board, albeit refreshed, will get it right this time.”

The Disney board has outlined a thorough process this time around. As the company said in its statement to VF, “It is a top priority of the Board to not only name a successor, but to position them for long-term success, and with more than two-and-a-half years remaining under Bob Iger’s term as CEO, the Succession Planning Committee is proceeding thoughtfully and carefully.” The internal candidates are said to be working with executive coaches, learning about parts of the business they don’t oversee, and receiving guidance directly from Iger. The public nature of the search means the pressure is on. A quick, small win in the optics department for aspirants might mean sitting close to Iger at events, or even dressing more like him. “Dana, like Bob, is a real star,” says Murphy. “When they walk into a room, the energy changes.” D’Amaro has the Iger vibe too. As Benioff of Salesforce puts it, “You can’t look at Josh without looking at Bob.”

Speaking of which, not everybody wants Iger to leave at all. “I don’t know what the rush is to make a change,” says analyst Reif Ehrlich. To which one of Hollywood’s top agents adds, “Look, the fucking president’s like 800 years old and he’s just starting to wobble. Bob’s unbelievable. He’s at the top of all of his powers.” But when he wrote his 2019 book The Ride of a Lifetime, Iger seemed to have made peace with saying goodbye. “We all want to believe we’re irreplaceable,” he wrote. “The trick is to be self-aware enough that you don’t cling to the notion that you are the only person who can do this job.” Now he and Disney just have to prove it.