After years of internal debate, the entertainment giant did a deal with a gambling company and will launch an ESPN betting app next month. Can it draw a bigger sports crowd without alienating Mickey’s fans?
8 min
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.”
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Strong family financial planning can help reduce taxes and support younger generations. From intrafamily loans and asset gifts to inheritance disclaimers, strategic cooperation can create meaningful financial benefits—when families have the trust and structure to make it work.
4 min
Happy is the family whose members—parents, grandparents and grown children—trust each other enough to cooperate on shared goals, especially financial ones. When that is truly the case, Uncle Sam’s tax rules can help as well.
This matters especially now that mortgage rates are above 7%, and many families are looking for ways to help younger members. If the elders have resources and are confident younger ones can cooperate, a family loan could make homeownership possible while providing the elders with a useful income stream.
Other strategies can actually lower taxes, such as when funding 529 plans or Roth IRAs, or when someone inherits a traditional IRA with required withdrawals larger than they will need.
Here are three strategies useful for functional families.
It is perfectly legal for families to lend money to a relative for a down payment or even a private mortgage.
But it is important not to cut corners, says Ryan McKeown, a CPA with Modern Wealth Enhancement in Minnesota. If the loan is for a down payment, be honest with the mortgage provider and have a formal agreement. The lender owes tax on the interest payments received.
If the loan is for a private mortgage, both sides should have legal representation with a formal written agreement, including payment terms. The lender owes tax on the interest, and the borrower often can deduct it if he or she itemizes.
To avoid IRS trouble, the interest rate shouldn’t be lower than the agency’s Applicable Federal Rate at the time of the loan. Currently that is about 5% for loans longer than nine years; about 4.5% for loans three to nine years; and about 4% for loans three years or less. Currently, traditional mortgage rates are generally above 7%.
In addition, the lender could use the $19,000 annual gift-tax exemption (described below) to forgive some or all of the interest or principal annually. If both lenders and borrowers are married, that is up to $76,000 a year. There is no tax for the borrower on such forgiveness, because it is from a gift.
If you’re going this route, McKeown advises against having a fixed plan to forgive the debt. Instead, do it in one-off letters specifying the amount—and keep careful records. Otherwise the IRS might try to treat the loan as a taxable gift.
Powerful tax-saving moves for families often use gift-tax provisions. Under current law, anyone can give anyone else up to $19,000 of assets annually, free of gift tax. That means a married couple with three grandchildren could give them a total of $114,000 in 2026.
The gifts can be cash or other assets, like stock. For noncash gifts, the cost basis—which is the starting point for measuring taxable gain after a sale—“carries over” to the recipient. So if someone buys $1,000 of stock and gives it away when it is worth $5,000, the recipient’s cost basis is $1,000. If the recipient later sells the shares for $8,000, the taxable gain is $7,000.
Here’s an example showing how gifts could save a family taxes. Grandma is a widow of modest means, while her child and spouse have prospered. The couple has two children, and they want to contribute $5,000 to a 529 college-savings plan for each—but they need to sell stock to do it. Their tax rate on the sale would be 18.8%, and they would need to sell about $11,000 of stock.
However, Grandma’s federal tax rate on the stock sale is 0%. If the couple gives $10,000 of shares to Grandma, she could sell them, pay no tax, and fund the grandchildren’s 529 plans. This saves about $1,000 of tax.
These moves are legal, and they could be used in other ways, such as to help a young person fund a Roth IRA.
But trust among family members is essential: Under the law, givers can’t put conditions on a gift. Grandma could use her stock proceeds to take a cruise, but she makes 529 contributions instead.
Mark Sellner, a retired tax attorney and CPA living in Sarasota, Fla., uses this strategy. His children sell stock he gives them and fund 529 plans for his grandchildren.
The family’s tax savings aren’t huge, but he likes other benefits. The sales by his children don’t boost his adjusted gross income, which in turn could raise his Medicare Irmaa premiums or his 3.8% surtax on net investment income.
Sellner doesn’t worry about his children using the funds for another purpose.
“There can’t be any strings attached to gifts. Of course, it is up to us to decide whether to make them in the future,” he says.
Two caveats: The “kiddie tax” applies to most children under age 24, and it is levied at the parents’ rate on investment income above $2,700 in 2026. Consider this before making gifts to a young person.
Investors who give away stock also forgo the step-up, an important provision that exempts assets held at death from capital-gains tax.
Sellner knows he’s losing a step-up, but says, “The children could use a little more now. Why should they wait 20 years to get it?”
A disclaimer is a highly useful strategy in which one heir renounces an inheritance in favor of another heir. Assuming family members cooperate, this can save taxes.
Here’s one example. Dad died and had a large traditional IRA that he left to Mom. She has enough assets and income to cover her expenses, and she lives in a state with a stiff estate tax. The inherited IRA would put her estate over the threshold.
Also surviving are three young-adult children. If Mom disclaims all or part of Dad’s IRA within nine months of his death, that amount could go directly to the children. They will have 10 years to empty the account, and the family as a whole will likely save estate and income taxes.
Disclaimers have many key details, especially regarding beneficiary documents. Although heirs have great freedom in choosing what assets to disclaim, the rules about who gets disclaimed property are rigid. It is best if the original owner names tiers of heirs so that if one disclaims, the next recipient is clear.
