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Ballsy Bezos: How His Midlife Crisis “Complexifies” His Relationship with the Washington Post

My intimation that the unseemly story of Jeff Bezos‘ steamy, seamy midlife crisis could be problematic for the Washington Post, which he owns (and which is exemplary for not only its political coverage, but also its cultural coverage), was truer than I knew when I tweeted this on Friday:

Jeff Bezos’ Twitter photo

Although he’s been almost universally hailed in the mainstream media as a hero for standing up to the sleaze-peddling National Enquirer, the self-righteous, adulterous Bezos, by foolishly putting himself at risk for a potential extortion attempt (and other possible complications that have been suggested, but not proven), arguably has compromised his suitability as a standard bearer for one of our country’s most distinguished newspapers.

Up until now, his generous financial support and hands-off editorial policy has strengthened WaPo, helping it to become one of the few newspapers augmenting its coverage, rather than cutting back. (It boasts two Pulitzer Prize-winning art critics.)

It’s not the extramarital affair itself that’s Bezos’ fatal flaw; it’s his reckless disregard of the potential for privacy breaches of his salacious text messages (see Anthony Weiner aka Carlos Danger). That unguarded indiscretion was dumbfoundingly dumb, given the Amazon mogul’s outsized technological (not to mention intellectual) prowess.

Friday’s NY Times article about the fallout from Bezos’ no-holds-barred, no-expenses-spared battle against American Media Inc., owner of the National Enquirer, suggests why his relationship with the Washington Post has “complexified”: His legal strategy could put Bezos at odds with WaPo’s ethos.

The Washington Post Teeshirt

Here’s why: To spearhead his attack on his attackers, WaPo’s owner has cozied up to some strange bedfellows, as reported by the NY Times’ Jim Rutenberg, Karen Weise and William K. Rashbaum.

Among those in Bezos’ legal camp, according to the NY Times report:

Martin Singer, who “is technically representing Mr. Bezos’ longtime security chief, Gavin de Becker” and “knows exactly how American Media works.” Having “not always worked on the virtuous side of the street,” Singer had “persuaded [the National Enquirer] to sit on [Andrea] Constand’s story in return for an exclusive interview with the former prime-time star [Bill Cosby]. And now he is Team Bezos,” in the words of the Times report.

Jonathan Sherman, who “previously represented American Media as it worked to squash negative stories about President Trump, according to a person familiar with the situation.” In other words, Sherman also may not have worked on what the Times calls, “the virtuous side of the street.”

—One of the founders of Sherman’s Boies Schiller Flexner law firm—superstar litigator David Boies—“defended the producer Harvey Weinstein against accusations of sexual harassment and abuse. As part of his services, he helped orchestrate a smear campaign against the alleged victims of the mogul’s sexual misconduct and hired…a private investigations firm…to undercut accusers and the journalists looking into Mr. Weinstein,” according to the Times report.

As James Stewart reported in the Times last September, the Times had “publicly fired Mr. Boies’s firm, which had been representing the newspaper, after learning that he had been personally involved in an undercover operation to smear Mr. Weinstein’s victims and deceive Times reporters.”

While the NY Times doesn’t explicitly state that Bezos’ lawyering-up choices were problematic in relation to his WaPo ownership, one can easily draw this inference from its report: A person whose defense is orchestrated by those who have worked to squelch reporters’ stories may not be the ideal owner of one of our country’s leading exemplars of a free press.

Can the Washington Post’s investigative journalists and its high-minded executive editor, Marty Baron, abide by the cringeworthy company now kept by their newspaper’s owner?

Marty Baron’s Twitter photo

For now, the Post’s Editorial Board has seen fit to publicly affirm that the paper’s editorial independence won’t be affected by its financial dependence:

The Enquirer appears to believe all news organizations operate as it does; it took for granted that Mr. Bezos would or could stifle The Post’s reporting. In fact, neither The Post nor the vast majority of U.S. media operate that way. Mr. Bezos has eschewed any role in directing the paper’s coverage from the beginning of his tenure as owner—and the writers and editors in the newsroom would reject any attempt by him to do so [emphasis added].

In his much publicized candid written statement outing American Media’s alleged extortion and blackmail attempt (which Elkan Abramowitz, an attorney for AMI chief executive David Pecker, maintains was neither extortion nor blackmail), Bezos wrote this:

My stewardship of The Post and my support of its mission, which will remain unswerving, is something I will be most proud of when I’m 90 and reviewing my life, if I’m lucky enough to live that long, regardless of any complexities it creates for me.

Given the “complexities” that his ownership could create for WaPo, his remaining there until he is “90 and reviewing my life” may depend upon more than physical longevity. What NY Times pundit Maureen Dowd hailed in her column as Bezos’ “PR debacle turned into a triumph,” could become a Pyrrhic victory—for both the lusty owner and his feisty newspaper.

That said, I’ve seen no indication in WaPo’s coverage that any of its analysts (not even Margaret Sullivan, its media columnist and the former public editor of the NY Times) foresee potentially troublesome ramifications for their newspaper from this “Bonfire of the Insanities” (as Sullivan termed it, riffing on this book).

Where’s the late novelist Tom Wolfe when we really need him? This would be great grist for a satiric social/economic opus.

Come to think of it, there’s another professional novelist who is uniquely qualified to fictionalize this drama in a roman à clef: Is MacKenzie Bezos sharpening her pencils?

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