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How Bob Chapek’s Disney Dream Turned Into an Instant Nightmare: Bob Iger “Wanted to See Me Fail”

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CitrixNews Staff
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How Bob Chapek’s Disney Dream Turned Into an Instant Nightmare: Bob Iger “Wanted to See Me Fail”
Bog Iger (L) and Bob Chapek - Disney - received 2020 Former CEO Bob Chapek, right, with his predecessor and successor, Bob Iger. Courtesy Disneyland Resort/Christian Thompson

Of all the stories and tales that Disney tells so well, perhaps none proved as fanciful, and lasted as long, as the fantasy that Bob Iger was going to retire.

Sure, he thought about it. And he talked about it. Bob’s public contemplations of retirement became a Hollywood tradition, like the Oscars, only it occurred slightly less frequently. Still, it was something of its own production. On different occasions, including that first conversation in my office in 20TK when he asked me who I thought should replace him (and I said “me”), Bob Iger dropped more breadcrumbs than Hansel and Gretel, but they never actually led anywhere.

First he was going to enter politics, then, after some initial feelers, thought better of it. Then, two years later, he publicly flirted with bringing an NFL franchise to Los Angeles, which never gained momentum. Each time, the entire management class underneath him readied for what could be a moment of transition. A number of us felt like the slipper would fit on our feet, if only Bob Iger would take it off in the first place.

Still, I did feel like I was being prepared for advancement. After that initial conversation about who his replacement should be, I started being invited to more functions, like board dinners, with corporate leadership. Those early engagements with the board also allowed me to participate in discussions about the company’s future. Bob’s long-standing relationship with many board members created powerful alliances for him, and he often used them to his advantage. As long as we were on the same team, those strong alliances were providing effective support for me as well.

By the end of 2016, my two main competitors for the top spot, Jay Rasulo and Tom Staggs, were gone. I realized I was genuinely in the running for the role. Brooks Barnes of The New York Times had called Tom “the only obvious candidate for the job

When Tom left, the chatter shifted, with some placing their bets on either Kevin Mayer or me crossing the finish line first. Kevin had also held key executive positions, including overseeing Disney’s acquisitions of Pixar, Marvel, and Lucasfilm, among others.

The question of who Bob’s successor would be took another unexpected turn in 2017, and by then, a lot had changed for me. I now had an office in Burbank as chairman of parks and resorts. The successful completion of Shanghai Disney had elevated my standing with Bob, and talk of his retirement was heating up again. When he asked to meet with me shortly before Thanksgiving, I couldn’t help but wonder if this was the moment I had been waiting for.

After a few years of waiting, working, and delivering profound value from my position in parks, I let myself fall into the trap once again.

By the fall of 2017, Bob had indicated that he was preparing to retire, and this time, he seemed serious about it. Just before the Thanksgiving holiday, he visited the headquarters of Imagineering,, the creative design division that was one of my responsibilities as chairman of Disney Parks, Experiences, and Products.

Around five o’clock, at the end of a fun but exhausting day, he asked if he could see me before he left the building.

He followed me into my Imagineering office and shut the door. “Bob, I have some news,” he said, his gaze unwavering.

My heart began to race. Could this be it?

“Bob, we are buying Fox, and I’m staying three more years. Have a great holiday,” he said bluntly before getting up and walking out.

It had happened again.

I felt as if I were on a football team lining up on the fifty-yard line for a drive and making it all the way to the five-yard line, only to be pushed back by holding calls, sacks, or too many players on the field. In football terms, at the very least, I was dealing with false starts and delay-of-game penalties that seemed completely arbitrary.

That holiday season, I felt dejected, thinking that I might never get my chance to truly achieve my dream.

Still, I had a job to do. So I did what I always do: I kept my head down and worked harder. Parks was doing well, and the best way to get the role I wanted was to be great at it. Kevin, from the reports of many, was not so subtle in his efforts to ramp up his public relations campaign for his candidacy—and in some circles he was anointed as the favorite to be Bob’s successor.

Nevertheless, Bob and other insiders repeatedly assured me that, despite Kevin’s maneuvers for the coveted position, they did not consider him a serious candidate. I had to push aside any thoughts of finishing as the runner-up, because I would consider that a great disappointment—or, as I had told my wife, Cindy, a failure.

To be clear, pushing aside thoughts and frustrations is easier when you have one of the best jobs at one of the biggest companies in the world. There’s always plenty to do, and when you’re a competitor, you’re always looking for ways to improve your score, which, for me, meant Disney’s bottom line.

Shanghai and Disneyland Paris were growing, and our new pricing systems in parks and cruises were paying dividends, literally. Our earnings report in November 2019 touted that revenues for the quarter increased 8 percent to $6.7 billion, and park operating income increased 17 percent to $1.4 billion.

The next month, I was working in my office, getting ready to spend the holidays with my family, when Bob requested another meeting with me.

I couldn’t help but think of the meeting years before when he had come in, also right before a holiday, to tell me he was staying.

He did have news.

In December 2019, he came into my office, closed the door, and this time delivered some different news. “Bob, I want you to know. I’m leaving.”

I didn’t roll my eyes. At least, I didn’t mean to.

In my mind, let’s just say I was less than convinced.

Okay, Bob, I thought.

Then he said the words that would change my life forever.

“I’ve told the board you’re my replacement.”

I barely said anything.

It wasn’t until Susan Arnold, the board’s lead independent director, called me the next day that I started to think this long-imagined fantasy might be real.

So, there I was one day in January 2020, sitting in The Rotunda, the company’s executive dining room located in Burbank atop Team Disney—the Michael D. Eisner Building. Susan Arnold had asked if I wanted to get lunch.

While The Rotunda is a place reserved for executives whose titles grant them the privilege of entry, the seating arrangement is more reminiscent of a high school lunchroom, except that everyone is much wealthier and more powerful. Each table represents a level in the company’s hierarchy, and the seating is determined by each employee’s rank. If Bob Iger were in town, he would sit at his preferred seat at essentially the twelve o’clock of the circular arrangement of tables. If not, the next-highest-ranking person would take his place.

It was the third week of January when Susan and I finally took our seats at this head table in the dining room. Unsure of what to expect, I wanted to be ready for anything. I had eaten at the head table many times before, but this was still an event for me. I was here with the head of our board. People saw.

We ordered salads and made small talk. But in truth, I didn’t have much of an appetite.

Before we started eating, Susan looked at me and said directly, “So I understand Bob has spoken with you.”

I simply nodded in response.

“Well, it’s going to happen, and it’s going to happen fast. Bob has decided relatively abruptly that he’s done, and the job is yours.”

Suddenly, the clinking of silverware and murmurs of nearby conversations faded away as I tried to process what I had just heard. I couldn’t believe it; I had so many questions. However, I was extremely careful to avoid asking the wrong ones, which could lead to another setback. I had been toyed with for six years.

It seemed like I was on the goal line. The last thing I wanted to do was draw a flag.

“How fast are we talking?” I asked her. I suddenly started thinking about the logistics—not just of doing the job, but of the announcement, which I assumed would be a thoughtful, drawn-out process. I was envisioning engaging with board members and some press, followed by a publicity tour and some meet and greets with key stakeholders over the next few months.

“It’s coming within two weeks, not months,” she said, her voice steady and firm.

As soon as the lunch was over, I called Cindy. At the time, we’d been married for nearly forty years, and if anyone knew how much this meant to me, it was her.

After more than a decade of waiting, I was, in fact, getting “it.”

Finally.

It was a victory for me, but it would come at a cost to others. Kevin Mayer, the presumed front-runner to some, announced he was leaving shortly after my appointment was made official. Kevin’s departure made him the third of Bob Iger’s top lieutenants over the last decade, along with Tom Staggs and Jay Rasulo, to leave.

Each of them believed he was the front-runner to be anointed team captain, convinced the job was his. Instead, in the end, Bob had just been toying with them.

During my follow-up conversations with Bob, he expressed a desire to remain involved and help me succeed in his former position. He also voiced his frustrations, saying, “I’m ready to leave, Bob. I’m sick of the earnings calls and all the board meetings.”

Those familiar with the situation suspected there were other reasons behind his decision to leave. One possibility was that his compensation wasn’t meeting his expectations, despite his receiving more than $100 million in stock awards from the Fox deal. Although he was a top player in the industry, his pay was considerably less than that of executives at Universal, Paramount, and Fox, all of which have more concentrated shareholder control from a smaller number of influential large investors versus widespread retail investors like Disney.

Later, I would discover there might be other reasons behind his “abrupt” decision.

After all the years of uncertainty and playmaking, I was surprised by how quickly everything came to a head. The timeline of my appointment moved at such a breakneck pace that I didn’t have the opportunity to meet with a single board member on the matter of my ascension and the transition.

As these events unfolded in a whirlwind, I learned that while Bob Iger would no longer be CEO, the board had agreed to allow him to stay on as “executive chairman of the board” and “creative director” for an additional two years. This meant I would have to report to both the board and Bob, although the interpretation of that varied depending on whom you asked. It certainly was confusing to me, as the story kept changing. Initially, I wasn’t too concerned about this arrangement. After all, Bob had always supported me. Why wouldn’t he continue to do so?

My naiveté about my dream job was about to end rather abruptly.

When Bob Iger released a statement naming me as his successor, the news stunned most people at the company, catching them entirely off guard. By the end of my first day on the job, I realized that I, too, had been caught off guard—and not in a good way.

As part of the announcement and rollout, we had arranged an interview with CNBC, with interviews with other outlets to follow. Sitting in matching directors’ chairs on the Disney studio lot, Bob and I were only a few minutes into our first interview with CNBC when I noticed things weren’t going as expected.

Bob usually appeared confident and optimistic in interviews, but he clearly didn’t feel that way during this one. I quickly understood I needed to do everything possible to avoid making the situation a fiasco.

I could almost feel the daggers Bob was hurling my way. When he introduced me to the world as his successor, he initially had said we had worked “extremely well” together. Seconds later, he went out of his way to clarify that “Actually, our senior management team has worked together quite well.”

That was it.

In response, throughout the exchange, I made every effort to compliment him for all the magic he had created for the company and acknowledge what an outstanding mentor he had been to me.

“I plan to follow in his footsteps and recognize I have some big shoes to fill,” I said. “We have a solid strategy, and I intend to continue implementing every part of that strategy.”

Whenever I glanced in Bob’s direction, his expression was ice-cold, and his shifting body language spoke volumes about how miserable and uncomfortable he felt. There were moments when he even appeared angry, with his jaws clenched.

Bob Iger was botching the handoff because I believe he didn’t want to let go of the ball.

What I didn’t know then is that the reality of that truth would leave no room for recovery.

It was so obvious that a reporter who had been covering the CEO transition shared his observation with me following the CNBC interview: it was apparent to him that Bob regretted everything and that the spotlight on me frustrated him. Why? Because I was now the one providing the play-by-play while he was relegated to adding color commentary.

I didn’t respond to the reporter. He was right.

The day after my announcement, I flew to New York to meet with investors and participate in more media interviews. I still hadn’t even been inside my new office at Disney, which I learned would not be the same one Bob had occupied as CEO.

Famous for liking to get to the office early and working out, Bob had a private shower in his office.

“You don’t need a shower in your office,” he told me.

I didn’t want to make things any more awkward than they already were, so I readily acquiesced.

I didn’t care about the trappings of a fancy office. I was just excited to have the job. I took a different office. The symbolism loomed large, as I would later experience.

While I might have landed the position, it seemed like Bob was now doing to me what he had previously done to Kevin, Tom, and Jay: playing me.

Two weeks later, the concerns I had during our CNBC interview began to play out openly. We were scheduled to hold our annual shareholder meeting in Raleigh in March, just before everything shut down because of COVID.

On the plane, I had asked Bob how he wanted to handle the Q&A from the board. He was aware I had never run a television network before, let alone a number of them, between ABC, ESPN, and other cable channels. Given my quick appointment, he understood there were still aspects of the company’s operations that were unfamiliar to me.

“How do you want to divide up these questions, Bob?” I asked, feeling increasingly anxious as my palms began to sweat. This was my first time addressing the shareholders as the new CEO.

“Oh, no. I’m not getting up there,” he informed me. “It’s all you.”

“I’ve had the job just two weeks, Bob,” I reminded him.

“Well, you have a binder. Study it,” he responded dismissively.

At that moment, I was 100 percent convinced he wanted to see me fail.

Of course, the very first question was about TV. It came from a conservative activist who threw me a curveball.

He wanted to know how I could sleep at night knowing the liberal bent of ABC News.

He proceeded to provide example after example before basically ending with, essentially, “What do you think of that, new guy?”

ABC News was a wholly owned subsidiary of Disney. So, as CEO, I was responsible for its operations and, apparently, alleged political bent.

I responded that ABC held itself to the highest standards of objectivity and balanced coverage.

I felt my answer hit his curveball satisfactorily. However, the feedback I received from both sides of the political spectrum within the company indicated neither side was totally satisfied. The liberal wing said I should have told him he was full of it, and those on the right thought I should have been more sympathetic. It seemed there was no way to win.

In that moment, though, Bob Iger had let me down.

Unfortunately, that wasn’t the last curveball that day.

While flying back from the Raleigh meeting, our finance chief, Christine McCarthy, suggested, “Hey, why not have our first one-on-one meeting now?”

Although it seemed like a normal request, Bob reacted explosively. “How could you dare disrespect me by having your first one-on-one in front of me?” he shouted, his face flushed and visibly upset.

In all the years we had worked together, this was the first time I had seen him demonstrate anger.

We rode most of the rest of the way in relative silence. As we flew above a country that was only beginning to confront a global pandemic, I, too, was realizing just how difficult my life was about to become.

Copyright © 2026 by Robert Alan Chapek and Don Yaeger. From the forthcoming book BEHIND THE CASTLE WALLS: My Thirty Years at the Happiest Place on Earth by Bob Chapek with Don Yaeger to be published by Gallery Books, an Imprint of Simon & Schuster, LLC. Printed by permission.

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Originally reported by Hollywood Reporter. Read the full story at the original source.