Welcome back to In the Room, and greetings from Seattle, where I’m gearing up to go
off-grid next week in the San Juan Islands. (No, I will not be making an appearance at the Bezos-Sánchez nuptials…) In this Friday’s issue, I’ll be taking questions from readers for In the Room’s first-ever mailbag. Send yours by replying to this email—and, please, feel free to ask anything.

In tonight’s issue, news and notes on the Larry Ellison-Trump dynamic, and how the relationship between two of the
world’s most powerful men stands to influence a number of impending deals big and small, from the TikTok sale to the Skydance-Paramount merger.

🍸 Plus, on the latest edition of The Grill Room, Oliver Darcy, founder and author of Status, joins me to reflect on the highs and hurdles of launching his own media venture: the challenges of building a sustainable business without external capital, the pressure to deliver distinctive reporting, the
looming influence of A.I., the enduring value of editorial integrity, and much more. Follow The Grill Room on Apple, Spotify, or wherever
you prefer to listen.

Also mentioned in this issue: Shari Redstone, David Ellison, Jeff Zucker, Elon Musk, Safra Catz, Adam White, Pat Dimon, Mike Waltz, Matt Murray, Will Lewis, Bari Weiss, J.D. Vance, and many more…

Let’s get started…

Front Office Sports to launch studio: Jeff Zucker is bringing together two of his RedBird IMI assets—Front Office Sports and Bright North Studios—to launch Front Office Sports Studios, a joint venture that will develop new film and television projects adapted from FOS’s coverage of the sports business. The new studio, led by filmmaker Pat Dimon, already has projects in the works with Skydance Sports, Paramount, Vice Sports, and others.

“The
streaming platforms, the studios—the one thing that everyone is looking for and everyone is buying is typically sports and sports-adjacent storylines,” Adam White, the founder and C.E.O. of Front Office Sports, told me this week for an episode of The Grill Room, which will post this Friday. “The amount of independent sports media companies are very few. … We can work with an Amazon, a Netflix, an ESPN, a Paramount. We have the ability to be Switzerland, which is really
advantageous for us. We can lean into a lot of the reporting storylines and access that we’ve been able to develop to have success.”
WaPo’s Wikification: The Washington Post is introducing a new feature that will allow sources mentioned in articles to annotate those stories, and engage with readers—part of a broader, ongoing overhaul of the business and the editorial product. In a memo to staff on Wednesday, executive editor
Matt Murray touted the initiative as a way to increase engagement on the site by hosting conversations “about our journalism on our own platforms, rather than losing those interactions to social media, where sources sometimes turn.”

Some veteran Posties will understandably chafe at a move that might undermine the authority and finality of their work—and potentially open them up to derision and finger-pointing on their own turf. Indeed, this semi-batshit crazy idea is
likely going to have some unintended consequences. “If I have a client quoted in The Washington Post, they can engage directly on the topics in their story, on the platform?!” one P.R. rep texted me after hearing about Matt’s announcement. “Literally a nightmare. … and a client’s wet dream. ‘I can say more to explain and double down on what I said!’” On the other hand, at least Will and Matt are trying something to reverse the paper’s
fortunes. Too bad that something could undermine the business.
The Bari report: Finally, before we jump headfirst into Ellisonworld, I was somewhat amused by a report this week from the aforementioned Oliver Darcy noting that David Ellison was interested in recruiting Bari Weiss to CBS News after he takes control of Paramount. Their meeting, late last year, read to me like the standard meet-and-greet many
media executives have sought out with Bari, a veritable darling of the Sun Valley media mogul set—so many of whom share her pro-Israel, anti-woke, stop-whining politics.

And while I have no doubt David floated his interest in working with Bari, I’m not sure what value she would derive from diverting attention away from her own hundred-million-dollar business to jump aboard a sinking broadcast network… as, what, an occasional 60 Minutes correspondent? Does it tell us
something about David’s politics? Sure! But so too does sitting ringside with Trump at a UFC event. And, by the way, if this is the media chew toy that has the CBS News crowd fired up, they’ve got a whole other thing coming to them.

And now, the main event…

I Now Pronounce You Donald & Larry

While the media world’s eyes are trained on the CBS–Trump settlement negotiations,
and its impact on the Ellison family’s tortured acquisition of Paramount, Larry himself has his eyes on a bigger prize at 1600 Pennsylvania Avenue: TikTok and Stargate.

Dylan Byers

In recent weeks, I’m told, Larry Ellison has had multiple private meetings with
President Trump—including one as recently as last weekend in the Oval Office, where the two men spent a great deal of time discussing the Iran-Israel War, among other topics. The centibillionaire Oracle chairman and longtime master of the universe is also a fervent supporter of Israel. Needless to say, the topic was rather timely.

Ellison and Trump have been close for ages, of course, though their relationship has never been as heavily scrutinized as the one
between the president and, say, Elon Musk. Indeed, somehow, like the database company he created, Larry has never garnered the same level of media attention as other generational entrepreneurs with comparable power and wealth. While the entire world will be mercilessly forced to observe Jeff Bezos’s second wedding in Venice this week, even the
Times can’t confirm whether Larry is on his fifth or his sixth marriage.

In any event, Larry and Don have several irons in the fire beyond international military conflicts, including Oracle’s interest in TikTok, the Stargate A.I. infrastructure initiative—and the Paramount-Skydance merger, which is being carried out by Ellison’s son,
David. The recent pilgrimages to 1600 Pennsylvania have thus garnered some attention from certain White House and White House–adjacent sources, who can’t help but speculate that the two men must be discussing those deals—but can’t know for certain, of course, since only two men were in the room. (As with all private meetings among principals who are not sources, it’s as hard to confirm the discussion of these pressing topics as it is to countenance that
such details would not be discussed. Alas.)

Meanwhile, Oracle remains in pole position to acquire TikTok’s U.S. business following a divestiture by ByteDance, according to sources with insight into Trump’s thinking. The deadline for that deal to close, originally slated for January, has been thrice punted—unconstitutionally, probably, but whatever—and is now September 17. Oracle C.E.O. Safra Catz is overseeing those negotiations for Larry, while Trump has tasked
Vice President J.D. Vance and now-former National Security Advisor Mike Waltz to handle the potential sale.

Meanwhile, Larry is at the center of the White House’s Stargate initiative, a joint venture between Oracle, OpenAI, Softbank, and Abu Dhabi state-owned investment firm MGX that plans to invest $500 billion in A.I. infrastructure over the next four years. Oracle is a provider of cloud infrastructure, and an equity investor, having put at least $7
billion into the project so far, according to The Information.

Wink,
Wink

Then there is the Paramount-Skydance deal, where Larry is trying to help his son gain control of
Shari Redstone’s dying media assets. Despite the intense media scrutiny around the deal—especially in light of ongoing mediation talks to settle Trump’s lawsuit against 60 Minutes—the investment is chump change by the standards of his TikTok deal and Stargate interests. This week, after one source posited that Larry might have used a recent meeting in the Oval to try to convince Trump to greenlight that deal, another source countered that Larry was far too savvy to give
Trump any leverage over him that might jeopardize his ambitions with TikTok and A.I. But the truth is that Oracle’s initial $7 billion Stargate investment is comparable to the $8 billion the Ellisons will pay to gain control of Shari’s National Amusements. And Stargate has way more upside.

Still, many in the media wonder why David’s deal still remains in limbo, given his close ties to the president. The negotiations have dragged on for months, and the current July 6
deadline could very well be extended again. Settlement talks between Trump and Paramount over the 60 Minutes suit remain ongoing; on Wednesday, the Journal reported that the mediator had proposed a $20 million settlement, with $17 million going to the Trump presidential library. In any case, every source with any insight into the matter has assured me that Trump’s lawsuit will not change the outcome of the deal. “Larry is all in on Trump. The fix and wink is in,” said one media
executive. “In the end, Larry will make sure Shari settles, and all will be fine.” (Representatives for Ellison declined to comment. The White House did not immediately respond to a request for comment.)

Obviously, Ellison has so far avoided being ensnared in the Paramount mishegas, and it’s unclear why he’d get involved now, with so much on the line for his own company. There’s also plenty of rampant speculation that he’s generally disengaged on the matter, and that it’s
really on David to carry this over the finish line. For whatever it’s worth, speaking outside the White House last week, days after one recent meeting with Larry, Trump himself told reporters that David “will do a great job” running Paramount. In their recent meeting, perhaps they talked about another shared topic of interest—how to manage their heirs.

Puck fashion correspondent Lauren Sherman and a rotating cast of industry insiders take you deep behind the scenes of
this multitrillion-dollar biz, from creative director switcheroos to M&A drama, D.T.C. downfalls, and magazine mishaps. Fashion People is an extension of Line Sheet, Lauren’s private email for Puck, where she tracks what’s happening beyond the press releases in fashion, beauty, and media. New episodes publish every Tuesday and Friday.

A professional-grade rundown on the business of sports from John Ourand, the industry’s preeminent journalist,
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