Finally, soon after I arrived in 1996, Kann’s board announced a $650 million plan to fix Telerate, internally called “Rolling Thunder,” which inevitably became known as “Rolling Blunder,” and which executives quoted in Fortune described variously as “schizophrenic,” “total confusion,” and worse. Customers complained that using “Dow Jones Markets” products was like buying a car you had to assemble yourself. Think: Coalition Provisional Authority.

Telerate led to a $900 million write-down in the fourth quarter of 1997. I don’t remember the building shaking at the time, but it may as well have. DJ really never recovered, while Bloomberg sped off without a glance in its rear-view mirror.

In a story earlier this year on Bloomberg’s “money machine,” Fortune’s Carol J. Loomis wrote: “in the annals of business, the fall of Dow Jones from its financial-information throne and the rise of Bloomberg must be counted one of the great competitive turnabouts in history.”

In the “annals of business,” one of the “great competitive turnabouts” is not something you want to be on the wrong side of. The ‘69 Cubs had one of those.

Today, a monument to Telerate sits in South Brunswick, New Jersey, in the form of a vast and mostly empty office complex built for the now defunct data-provider. Walking through South Brunswick is like visiting the set of “The Omega Man,” the 1971 Charlton Heston movie about the earth’s population being wiped out by biological weapons. The buildings are there, but all the people are gone.

A more symbolic but telling venture was WBIS, also called, “S+,” an over-the-air business-and-sports TV channel in a joint venture with the conglomerate ITT Corp. The station’s slogan—“Sports, money, and, oh yeah, life”—was much mocked by us newsroom know-it-alls, but in fact it did foreshadow the corporate humbug that would come to mark even mundane internal communications.

One day, I was riding up from the newsroom on the tenth floor to the cafeteria on the fourteenth. The elevator stopped on eleven — ding!—and about two dozen chattering twenty-five-year-olds, new WBIS employees, shuffled on. That happened every day until July1997, the day the elevator opened onto a gutted twelfth floor. The reception desk was gone and wires dangled from the ceiling panels. A single maintenance worker got on. Ding!

In the wake of Telerate, etc., dissident members of the Bancroft family, which controls DJ’s voting shares, began to speak up, with some calling for Kann’s ouster. One heir, Elizabeth Goth, was quoted as saying—correctly—that the problems at Dow Jones were more systemic and more deeply rooted than one troubled unit. “There is a history with this company,” she said. “We have had questionable outcome after questionable outcome in various business deals.”

This is 1998.

Defenders of Kann, who didn’t reply to requests for comment, will say that this is all old news, and it is. They will also say he deserves credit for launching Weekend Journal, Personal Journal, and the database company Factiva; for making the online Journal a pay site, redesigning the paper, and other measures. And they’re right.

But as they say on Wall Street, all that’s not going to move the needle, generate enough earnings to make a difference and build the financial base to support the Journal through down ad cycles and difficult industry transformations.

Look, I don’t say being CEO of Dow Jones is easy.

But to me, the most regrettable chapter wasn’t Telerate, but repeating the mistake of underinvestment during the late-1990s tech bubble, when financial-service and tech ads made the Journal on some mornings as thick as a phone book.

Don’t take my word for it, ask Zannino, who is talking here about investing to spread out the paper’s advertising beyond financial and tech ads, but might as well have been speaking more generally. “In hindsight, sure, it would be hard for me not to say we should have been diversifying (our advertisers) back then. Next time.”

He said that to Newsweek in 2003, when he was DJ’s relatively new chief operating officer.

And while DJ was nibbling around the edges, trying to squeeze both growth and dividends out of a single newspaper and a handful of other stuff, mostly by beating the staff like so many rented mules, others acted like capitalists—you know, “free markets, free men,” and all that.

In the early 1990s when Kann took over, Thomson Corp. was a newspaper company that had expanded into textbook and law book publishing. In 1996, it bought West Publishing. Last year, its legal division alone posted operating profits of $1.1 billion, ten times that of all of Dow Jones. True, it sold off its newspapers in 2000, but it certainly could have supported them during this transition from print to digits.

Dean Starkman Dean Starkman runs The Audit, CJR's business section, and is the author of The Watchdog That Didn't Bark: The Financial Crisis and the Disappearance of Investigative Journalism (Columbia University Press, January 2014). Follow Dean on Twitter: @deanstarkman.