In early 2019, an analyst asked Disney Chief Executive Bob Iger if sports betting could coexist with the House of Mouse’s brand. He said he didn’t see the company facilitating gambling in any way.

Just four years later, the world’s most beloved name in family entertainment is going all-in on sports betting.

In August, the company struck a 10-year deal with sports-betting company Penn Entertainment to bring gambling to Disney’s ESPN sports network. Sports fans will be able to wager on games on their phones through a new app called ESPN Bet that accepts bets through Penn’s sportsbook.

The idea of gambling under the same roof as Disney has roiled some company executives and employees who feel it will damage the brand that is synonymous with princesses and talking cartoon ducks. In the last year, at least one large investor warned Disney that it might have to sell some of its Disney stake if the company embraced betting.

But for ESPN President Jimmy Pitaro and Iger, who saw his two adult sons glued to gambling apps on their smartphones, the chance to engage a younger male audience, and the money, were eventually too good to pass up. Penn will pay Disney $1.5 billion in cash while ESPN will receive warrants worth about $500 million to purchase shares in the gambling company. Penn will operate the app and Disney will help market it.

This is how sports in America works. Fans watch and they bet—particularly young men between the ages of 18 and 34—often making multiple complicated bets during a live sporting event. They can wager on how many 3-pointers a basketball player will sink or who will catch the final fly ball in a baseball game. It is huge on college campuses.

Wagering on games ballooned after a 2018 Supreme Court ruling cleared the way for states to adopt it. It is legal in 38 states and the District of Columbia. Last year, online sports gambling generated $7.6 billion in revenue—the amount companies received after paying out winning bets. Next year, revenue is expected to grow to $11.8 billion, according to Eilers & Krejcik Gaming, an industry consulting firm.

ESPN, like more traditional TV networks, is struggling with the decline in cable TV subscribers and the rising cost of sports-broadcasting rights. Sports leagues and legions of startups have embraced gambling, while large media companies have homed in on betting as one of the best ways to expand.

But Disney employees, more than most other workers, feel that their company stands for a set of wholesome ideals—something more than making money.

In mid-2022, Jenny Cohen, a Disney veteran who had been promoted to head of corporate social responsibility a year earlier, raised concerns about a potential foray into sports betting to top executives at Disney’s Burbank, Calif., headquarters and leaders at ESPN, urging them to reconsider their plan to strike a deal with a sports-betting operator.

She told her colleagues, and Disney’s CEO at the time, Bob Chapek, that sports betting would tarnish the Disney brand, according to people familiar with the discussions. Consumers could start associating Disney with gambling addiction, she argued. As this discussion brewed, Disney was already managing a crisis with many employees who felt their employer didn’t take enough of a stand against a Florida bill that prohibits instruction on sexual orientation or gender identity for young students, known by its opponents as the “Don’t Say Gay” legislation.

Around the same time, BlackRock, the investment giant which uses socially-conscious environmental, social and governance—or ESG—criteria to guide some of its investing decisions, contacted Disney’s investor relations staff. It warned Disney that if the company did a deal with a sportsbook, ESG rules may require some of its European funds to reduce their Disney stakes, people familiar with the matter said.

Disney is also contending with a fresh push by activist investor Nelson Peltz’s Trian Fund Management to secure multiple board seats, The Journal reported this week. Trian thinks Disney’s stock is undervalued and that Disney needs a board that is more focused and accountable. It is unclear what other changes the hedge fund plans to seek. Peltz and Trian haven’t publicly taken a position on ESPN and gambling.

There are Disney fans, Disney+ subscribers and theme park visitors that likely have no idea that ESPN is part of Disney, but internally, Disney’s businesses are perceived as interconnected parts of one overarching corporate brand: a place where dreams come true. The ESPN+ streaming service is offered as part of Disney’s streaming bundle, and ESPN promotes shows from other Disney-owned networks during its broadcasts, and vice versa. This week, for example, ABC late-night host Jimmy Kimmel appeared on ESPN2’s football show the “Manningcast.”

“My job is to protect the brand at all costs,” said Pitaro, in an interview. “I am the custodian of the ESPN brand, and we needed to make sure that whoever we went with on this journey was someone that we could trust.”

Disney first began flirting with sports betting in March 2019, when it completed its $71.3 billion acquisition of Fox’s major entertainment assets, which included a 6% stake in sports betting company DraftKings.

At the time, some of Iger’s top lieutenants urged him to take a bigger ownership stake in the gambling company, but Iger resisted, arguing that betting wasn’t on-brand for Disney.

Without his blessing, sports-betting discussions stalled until Iger stepped down as CEO in February of 2020, and the board named his veteran head of parks, Chapek, to replace him.

Chapek had a much different view of gambling. He told associates that he was “not that precious about the Disney brand,” compared with his predecessor when it came to sports betting.

He began exploring a potential partnership with a sportsbook, and Disney started up talks with DraftKings, which now has more than 30% share of the sports-betting market. At the time, DraftKings had a marketing arrangement with ESPN, by which it would link ESPN.com readers to make online bets through DraftKings.

Despite Cohen’s objections, Disney signaled that it was seeking a new deal worth around $3 billion over a decade, and Chapek and Pitaro gave news interviews, saying that ESPN customers wanted a “seamless” betting option as part of the sports-viewing experience. ESPN had already embraced sports betting within its programming, including in its “Daily Wager” show, which analyzes odds for sports matchups.

Pitaro intensified his matchmaking efforts with DraftKings, but from the outset, the two companies were far apart. Disney asked for tens of millions of dollars a year more than DraftKings was willing to pay, according to a person familiar with the matter.

Eventually, DraftKings offered around $100 million a year for ESPN to use its sportsbook, but DraftKings wanted its brand included on any app or marketing as part of the deal. That was a nonstarter for Pitaro. He wanted solo ESPN branding.

His team began negotiating with Rush Street Interactive, a smaller, Chicago-based gambling company. RSI offered ESPN more than $100 million a year, but a deal never came together.

Pitaro felt pressure to secure ESPN’s future, particularly among young male fans who increasingly expect betting to be a seamlessly-integrated part of the sports-watching experience. By this time, Iger had returned to Disney as its CEO after the board ousted Chapek in November of last year, and the company was hard at work on plans to remake ESPN as a streaming-focused platform. Iger had told interviewers that he had seen the writing on the wall for the traditional TV business, which was showing signs of being on its deathbed.

Overall, Disney was struggling. Its foundering share price had drawn attacks from activist investors including both Peltz and Dan Loeb’s Third Point, its streaming business was bleeding cash and its whole traditional television business, more than just ESPN, was suffering as more people dropped their cable TV subscriptions in favor of streaming. Disney is currently exploring potential strategic partners for ESPN and has had talks with major sports leagues about it.

Iger quickly set about trimming fat, announcing $5.5 billion in budget cuts and the elimination of 7,000 positions, around 3% of Disney’s total global workforce.

Soon, Iger warmed up to sports betting. His adult sons’ use of sports-betting apps opened his eyes to its popularity with a younger audience, he told associates. He said that it is “inevitable” that sports-watching and sports-betting will go hand-in-hand, and he blessed Pitaro’s efforts to find Disney a partner. Getting involved with gambling was the only way to ensure that ESPN is able to continue to attract younger audiences, he reasoned.

Along came Penn, the Wyomissing, Pa.-based casino operator turned sports-betting company that also needed a makeover after it got into regulatory and reputational trouble over its ownership of sports-media company Barstool Sports, founded by Dave Portnoy. Several women have accused Portnoy of sexual misconduct—allegations he has denied.

Penn runs casinos and racetracks in smaller regional markets like Lake Charles, La., Biloxi, Miss., and York, Pa., and its CEO Jay Snowden wanted to remake the company into a digital gambling powerhouse.

Snowden first met Pitaro in his office for about a 90-minute meeting earlier this year. Pitaro left thinking Snowden was “a straight shooter” who knew what he was doing, the ESPN executive said.

Pitaro quickly deployed teams working on ESPN’s sports-betting, tech, strategy and marketing into parallel talks with Penn to flesh out what a potential partnership could look like. He said Penn’s technology, including the functionality and design of the app, stood out. In addition, Disney views Penn’s tiny market share as an advantage because ESPN can have more control over branding the app and not have to share the spotlight with a better-established player, according to people familiar with Disney’s stance.

There was a key requirement to move forward with a Disney deal. Penn had to dump Barstool.

When Penn began acquiring Barstool in a series of transactions starting in 2020, the gambling company hoped it would help it build a young customer base. Barstool runs an extensive sports-content operation that has drawn criticism for sexism and some of its employees’ crude behaviour. Gambling regulators ultimately fined Penn for violating rules about marketing to people under the age of 21 and scrutinised advertisements that appeared to promise financial success. Barstool said it was being sarcastic.

Pitaro informed Iger of the talks in an early June meeting, and the CEO liked the idea of a partnership with Penn. Pitaro had long held out hope that Disney could fashion a deal with DraftKings, a market-leading online gambling company that was seen by some inside Disney as a natural fit, but the negotiations had become bogged down.

Pitaro suggested that they end talks with DraftKings. Iger, who felt that the negotiations had gone on too long and DraftKings’ demands weren’t reasonable, agreed. Besides, Penn was offering a better price. It was time to move on.

In June, Pitaro presented the Penn deal to Disney’s board at a meeting in Anaheim, Calif., and in early August, the day before Disney was set to announce third-quarter financial results, Disney announced the $2 billion deal.

Penn needed to rebrand the Barstool Sportsbook app into ESPN Bet under the new deal. To quickly make room for Disney, the company sold Barstool back to Portnoy for $1, just six months after fully acquiring the company. Penn kept the database of 1.5 million online betting customers it has accrued, which the company aims to retain under the ESPN name.

ESPN and Penn have the option to walk away from the partnership in three years if the venture hasn’t captured a minimum market share target. Snowden declined to say the exact target, but said it was around 10%.

“There’s only one ESPN,” Snowden said. “If we were going to make a pivot, there was really one option to do that, and that was with what is the only name that is truly synonymous with sports in the United States.”

ESPN sports programming won’t be pushed into the betting app when it launches in November so as not to slow down the betting experience, Snowden said. Instead, the goal is for ESPN viewers and readers to easily switch back and forth between sports and the betting app.

Pitaro said that many on-air stars are eager to get involved with ESPN Bet, and the company plans to announce an expanded talent lineup to host and promote its gambling-related products and shows. ESPN forged a partnership with former NFL punter and foul-mouthed YouTube star Pat McAfee, who is known for hosting broadcasts in sleeveless T-shirts and making occasional off-colour jokes. He will promote ESPN Bet to his audience.

ESPN is also considering alternative broadcasts of games focused on betting, similar to the popular version of Monday Night Football hosted by former NFL stars and brothers Eli and Peyton Manning that airs on ESPN2 and ESPN+, and plans to promote betting to its growing fantasy-sports audience. Pitaro said its fantasy platform is expected to reach more than 12 million users this year, a 10% increase from the previous year.

“Getting into sports betting is a perceived business necessity for ESPN,” said John Kosner, a former ESPN executive who now runs Kosner Media. “I think this decision has to do more with ESPN’s manifest destiny than Disney’s position on branding.”

The first year in retirement is often the most difficult. But it also can set the stage for how you’ll fill the years ahead—both financially and psychologically. Stephen Kreider Yoder, a longtime Wall Street Journal editor, joined his wife, Karen Kreider Yoder, in retirement a year ago. In this monthly Retirement Rookies column, the 66-year-olds chronicle some of the issues they are dealing with early in retirement.

Karen

In the kitchen, I look up at my woven companions—16 baskets atop the cabinets. They’re from a dozen countries, and they radiate warm memories.

But wait, do I need so many baskets? And 40 more are around the house, many as decorations or stored in closets.

I’m trying to get rid of stuff methodically early in retirement, and it’s beginning to feel like a steady job. There’s no urgency. But when the time comes for a smaller place, I want to be ready. That time could come any time.

I want to winnow our possessions before there’s a health crisis or moving van at the door, while I can do the hard work of organizing and categorizing, of identifying what I need long-term, what to disperse and what to pitch.

It’s partly psychological. As I age, I find I have less room in my head to keep track of things. And the sheer numbers of some possessions create a growing mental tension.

We were ahead of the game when we retired. We moved a dozen times in 44 years, each time purging a bit. Helping our parents downsize inspired us often to do a sweep of our own when we got home.

Now that we’re both retired, I’ve created some downsizing categories to keep me from being overwhelmed:

• Don’t use it, don’t need it. Old electronics and orphaned cords. Knickknacks without sentimental value. My 20 thimbles from around the world, only one of which I ever use. The 150 beautifully sharpened No. 2 pencils in a row of blue-and-white ceramic pots, one labeled “Pencil Collectors Society.”

I’ll use perhaps a dozen pencils the rest of my life. The others can be off to Goodwill now, along with everything else in this category.

• Things we use now but won’t in a smaller space. Some of the guest-room furniture, extra chairs, large house plants, the piano, a rusty wheelbarrow. We should do an inventory now and label what we’ll ditch when we move.

• Stuff only I can handle. My childhood report cards, recital programs, work accomplishments, letters and such are a priority for thinning out now. Nobody else can make sense of them, but it can feel like throwing away bits of myself.

“But Mom, you have to save all of that,” says our son Isaac. “It’s like your personal legacy.” Maybe I’ll keep more than I intended, for our boys to root through as a window into my youth. (But, I wonder, will they really care about those report cards?) At least, though, I should organize it.

• Family heirlooms and mementos. These, too, are hard to part with, imbued with family history and shared memories.

We aren’t antiquers, but we do have a few elegant old Japanese tansu cabinets the kids grew up with. And I have about 25 quilts, some I made starting at age 7, and many from family and friends. They are works of art and full of memories but too many to fit in a condo.

The boys say they want some but are still too mobile, so at least I should make a plan for who gets what.

• Things I want by my side through older years. Family photos. My Japanese pottery. Journals from our travels. My quilt frame.

And baskets. I have always cherished handmade baskets. My first is from South Dakota, where at 16 I learned willow-basket making from two local weavers. I can’t part with it.

When our son Levi is home, we eat sticky rice with our fingers out of little lidded Laotian rice baskets, recalling Laos when he was age 2 and clutched his sticky-rice basket as we bicycled around Luang Prabang.

In our guest-room closet is a Japanese backpack basket—a gift from a student’s family—whose weaver was a Japanese National Treasure. In my reading room is a basket we bought in a Philippines market in 1987, not knowing it was for a baby until locals pointed and laughed knowingly. It became a bassinet to our three babies, and it’s a treasure.

Five dozen baskets is too many now. How many is just enough?

Steve

A classical guitar in its case stares at me from a corner of the bedroom. “Play me,” it taunts, and I look the other way.

Maybe it’s time I got rid of my lonely 1972 Alvarez Yairi as part of our gradual downsizing.

A tougher thought: I should probably also downsize my pipe dream of someday playing a guitar even moderately well, along with dozens of other unrequited ambitions I’ve clung to for decades. And I’ve got a few erstwhile passions I might best surrender now as well.

Karen talks of ditching stuff, and I’ve got plenty of boxfuls to sacrifice—textbooks, decrepit power tools, hardware that definitely might come in handy some time.

I also should release one or both of my vintage Honda motorcycles, which I’m sentimentally attached to but haven’t ridden in ages.

But for me, downsizing is more than getting rid of stuff. It’s about getting rid of conceptions of myself—of who I was, who I am and who I want to be.

That is, I should sell my motorcycles not just because they take space, but also because I think I’ve permanently moved on from motorcycling, my passion for decades starting at age 12.

Same with my skis and skiing.

Retirement has had a way of giving me permission to begin letting go—of my professional identity, my urge to do financial planning without help, the delusion that I’ll be fit forever. That permission makes it a good time for some wanna-do triage.

There are things I still intend to get to, now that I have more time. I want to weld better, brush up my Spanish, improve my swimming, study more history and learn to drive an 18-wheeler. There are activities we’re already stepping up, like traveling more in Africa, cycling around America, visiting family and seeking long-term volunteering opportunities that match our skills.

But finding time for all of it requires that I liberate other I-will-get-to-its that are increasingly a mental burden. I will probably never learn Arabic and should forgive myself of that, and French. I can get rid of the beer-brewing equipment I bought when I was 23 and discharge the notion that I’ll ever learn to use it.

I will probably never write a book; may I free myself from that weight? I hereby declare I can die happy enough without visiting Machu Picchu, the Galápagos or Rome as I’d once hoped to do. There are plenty of other places we want to go, and not time for everywhere.

Our house is a standing to-do list of fun projects I’ve put off and may never get to—or shouldn’t, lest I fall off a ladder and meet an untimely demise. Let’s just release some of those projects, too.

When I bought the Alvarez in 1981, my guitar teacher said I had talent. His kind words kindled my decadeslong conviction that I would learn to play it well, eventually. We moved to Japan the next year, and I took along the guitar but didn’t find a teacher—temporarily, I told myself.

The guitar moved with us many times until 2012, when Karen bought me lessons with a fabulous teacher for my birthday and I began learning again. I did pretty well, even playing in a few modest recitals. But I dropped it—temporarily, I said—when we moved out of town for a year.

Now there it sits. It’s time to set it free.

Or is it? I finally have the bandwidth. I just opened the case, and only one string is broken, a good omen. Maybe this time I really can learn to play it.