When’s the best time to sell a high-profile media property? Well, probably not during a pandemic-induced recession. And also maybe not amid the systemic, long-term decline in publishing—a sector that was challenging (to say the least) even pre-COVID. And also probably not when said media property is reportedly losing millions of dollars per year.

That’s the unenviable challenge Verizon has in trying to sell HuffPost. (News broke last week that the telecom giant’s Verizon Media division has been seriously shopping the site formerly known as The Huffington Post, which it’s owned since 2015 when it acquired and absorbed HuffPost’s parent, AOL.)

These days, once-mighty media properties tend to change hands in fire-sale transactions, but we were reminded of the publishing industry’s cash-flush glory days when we chanced across a front-page story, headlined “Murdoch shops ‘TV Guide,’” from our May 21, 1990 issue as part of our continuing “90 Years of Ad Age” deep-dive. It wasn’t exactly the perfect moment to sell—as Ad Age noted in another story in that issue, publishers were facing “a continuing ad-page shortage” (that softness foreshadowed the U.S. economy formally entering an eight-month recession that would begin in July of that year)—but Rupert Murdoch was still able to credibly slap a $2.6 billion price tag on the digest-sized print weekly.

Though Murdoch’s News Corp. had bought TV Guide’s parent, Triangle Publications, for $3 billion just two years earlier, Ad Age’s publishing reporter at the time, Scott Donaton, noted that the company needed the money to help pay down corporate debt and to “let Mr. Murdoch focus his resources on other holdings” including Sky Television in the U.K. and the fledgling Fox Broadcasting Co. in the U.S. At the time, TV Guide still sold more than 3,000 ad pages per year and had circulation topping 15 million.

A News Corp. spokesperson denied in May 1990 that the title was for sale, dismissing it as a “ridiculous and silly” rumor. “Finding a buyer may not be easy,” Donaton reported, as “only a handful of companies could afford the hefty price tag”—and a looming recession surely didn’t help either.

After the publication of the story, an angry Rupert Murdoch called Rance Crain, then editor-in-chief of Ad Age, and bet him $1 million that he couldn’t produce a single source backing up the story. Crain turned down the wager, later recounting that “At the time I thought it was a spur-of-the-moment gesture, but now I think it was a carefully constructed ploy to get me to reveal our sources—which he of all people should have known we would never do.” The proposed bet got plenty of media attention, which had Crain wondering: “Could it be that Mr. Murdoch, in his own unique style, was trying to drum up buyers for TV Guide after his earlier, lower-
key efforts had failed?”

In the end, Murdoch sold TV Guide only in 1998, offloading it to a new joint venture created with the parent company of the Prevue program-listing TV channel (which would later become the TV Guide Channel). TV Guide’s circ had sunk to 13 million by this point, and the transaction was executed in $800,000 in cash and $1.2 billion in stock.

In other words, Murdoch waited way too long to sell.

Which reminds of us of Verizon. It’s worth noting that around this time last year it was also said to be shopping HuffPost. By November 2019, Verizon Media CEO Guru Gowrappan was confidently taking the stage at a media conference to declare that, “We are not selling HuffPost. It’s so core to our content.”