Good evening, I’m Dylan Byers.

Welcome back to In The Room, my bi-weekly private email that takes you behind the scenes of the American media. Tonight, an inside look at what’s real and what’s not in Mike Bloomberg’s alleged interest in a Journal or Post acquisition—and what it says about where the Bloomberg empire may be headed.

It was a silly and harmless joke, meant to get a knowing wink kind of a laugh. Indeed, as anyone in Manhattan society well knew, Taylor was the far more charming and telegenic member of the couple. But it also may have insinuated Bloomberg’s perpetually restless and youthful energy that has not ebbed since he built the Bloomberg L.P. empire forty years ago.

Preternaturally technocratic, now 81, Bloomberg remains one of the most tireless and ambitious people in the game to this day, and he does not sit still for long. Upon returning to his namesake company after 12 years as mayor, he forewent any sort of sinecure and took back the reins of his company, only to start floating the idea of a presidential bid two years later. He finally ran for president in 2020, at the end of a protracted and highly public will-he-or-won’t-he period, spending nearly $1 billion of his own money in the process before being cut down to size by Elizabeth Warren in Las Vegas. (Funny how fast you can lose a fortune in that town.)

Throughout his career, Bloomberg’s restless ambition has turned time and again to an expansion of his media assets. For years, the Michael’s lunch crowd poked fun at Bloomberg Media and its top editor, the bow-tied Matt Winkler, until it became a certifiable competitor with the Wall Street Journal. Over the years, in fact, Bloomberg Media hired legends like Norman Pearlstine as chief content officer and Andy Lack to run the television unit. After Bloomberg bought the then-moribund Businessweek for essentially nothing other than its operating costs, Josh Tyrangiel created a highly ambitious digital operation. Justin Smith was eventually hired away from Atlantic Media to become C.E.O. John Micklethwait, the charming and august editor of The Economist, long rumored to be “Mike’s” favorite magazine, relocated to New York to run Bloomberg News. (At Bloomberg, everyone refers to Bloomberg as “Mike.”)

Whether because he loves media or is worth nearly $80 billion, Bloomberg has long been considered a fantasy media acquirer for the fourth estate. At various points, he has been said to have an interest in acquiring The New York Times, The Wall Street Journal, The Financial Times, and The Economist. One memorable anecdote from a New York magazine article by Gabe Sherman, published in 2012, depicts Bloomberg at breakfast at a hotel in Paris asking a friend, “Do you think I could buy The New York Times?” The friend then said that he didn’t think the paper was sold in the hotel. So Bloomberg responded: “No, do you think I could buy the Times?” Years later, Sherman would report that Bloomberg had pitched the idea to Arthur Sulzberger.

Bloomberg’s motivation for these pursuits, or at least for floating these pursuits, may stem from business savvy, boredom, or curiosity. He also likely understands that Bloomberg News, for all of its incredible success and ongoing expansion, has never achieved the same influence or cultural relevance as some of its more storied, if less financially secure, competitors. Owning a title like the Times or the Journal conveys a level of cachet that Bloomberg News does not. The Economist is known and revered by well-educated news consumers the world over. Bloomberg Businessweek is not. And so on.

It is therefore not all that surprising that, once again, someone in Bloomberg’s orbit has floated the idea of a major media acquisition. Just before Christmas, Axios’s Mike Allen and Sara Fischer, two surefire take-it-to-the-bank journalists, reported that Bloomberg was interested in acquiring either Dow Jones, the parent company of the Wall Street Journal, or Jeff Bezos’s Washington Post. The report may have felt to some like a trial balloon, the work of a Kevin Sheekey-type restless deputy. After all, Bloomberg’s well-liked longtime government affairs guru and former campaign manager is the one who Bloomberg jokingly blames for forcing him to run for president by, in part, repeatedly leaking Bloomberg’s interest in the idea to the media.

Bloomberg L.P. moved fast to quash the report. “There have been no conversations with anyone or either organization about an acquisition,” Bloomberg L.P. spokesman Ty Trippet said in a statement. “The company has no interest in acquiring either.” And to be sure, if Bloomberg was serious about pursuing such an acquisition, a leak to the media almost certainly wouldn’t be the way he’d go about doing it. He would have called Rupert Murdoch or Bezos directly and started the negotiations in private. Indeed, these are probably the only two media owners whom he might count as peers.

Then again, it’s not at all clear that either one of those men is interested in selling their media assets. One plausible scenario is that Bloomberg mused aloud on a few occasions about these ideas, perhaps boasting that he could run either paper better than it was being operated today, and someone else in the inner circle got so excited about the hypothetical that they passed it to Allen & Fischer. Maybe. Maybe not. Either way, as is often the case, only Mike knows.

Murdoch has always been content for the Journal to stay in its lane and serve as the bible for the global business community. For a time, at least, Bezos seemed intent on making the Post truly competitive with the Times. But those ambitions have been put in check after the business started churning subscribers and losing ad revenue after the fire and fury of the Trump years. Meanwhile, the paper has been beset by a crisis of faith in Fred Ryan, its publisher and C.E.O. Critics inside the building, including executive editor Sally Buzbee, have blamed Ryan for failing to set the Post up for sustained success in the post-Trump era, a la the Times. (Buzbee has denied this.)

Ryan is currently trying to repair relations with staff after he pottered out of a town hall after he announced layoffs but refused to take questions from staff. In recent weeks, he has held private one-on-one meetings with some top reporters. It may not be enough to stem the tide, however. A procession of the Post’s business and editorial stars (Shailesh Prakash, Steven Ginsberg, David Fahrenthold, etcetera) have left in the last year while would-be recruits (Jonathan Swan, Jonathan Martin) have passed on generous offers. The latest loss, described by various Post sources as a “gut punch” to the organization, is Eli Saslow, a homegrown Postie in his prime who left for—where else?—the Times.

Unless Bezos wakes up one morning and decides to overhaul the Post, Mike Bloomberg may be the sole media entrepreneur with the ambition—and Bloomberg News the sole U.S.-based outlet with the infrastructure and financial capital—to give the Times a run for its money. And an acquisition of the Journal or the Post could conceivably get him the subscriber base and cachet to start that effort in earnest. A Journal acquisition would make Bloomberg the indisputable leader in business and financial news, while a Post acquisition would confer unparalleled political influence, catapult the combined asset into a global news behemoth overnight, and immediately make it competitive with the Times, if not superior. And sure, none of it may happen. But an $80-billion man can dream, and dream aloud.

The only difference between now and all those other previous reports is that nowadays—with the Post newsroom on edge and The Journal reeling from the defenestration of top editor Matt Murray in favor of Emma Tucker, a Murdoch favorite—it may not just be Bloomberg’s dream. Hundreds of journalists are probably going to sleep fantasizing about his potential ownership, too.