If you haven’t seen Jon Stewart’s evisceration of former-baseball-star-turned-investment-guru-turned-bankrupt Lenny Dykstra, as well as some of his fawning admirers in the press, take a few minutes to watch a classic.

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Lenny Dykstra’s Financial Career
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Our interest here is the business-press angle, of course. Now, “liberal media” scourge Bernard Goldberg of Real Sports isn’t exactly David Faber, but he reported a business story—one that made Dykstra out to be some kind of financial genius—so good enough for me. This from HBO’s summary of the segment:

Leaving the game in 1996, Dykstra went head-first into the business world, embarking on another winning career. Most recently, he became a prominent, remarkably successful stock investor and consultant, writing a column for TheStreet.com, and serves as president of several privately held companies. Correspondent Bernard Goldberg goes behind the scenes with high-flying California native Lenny Dykstra, the business world’s most unlikely mogul.

The Daily Show catches Goldberg with some gems:

Now the guy who probably couldn’t spell “financial guru” in his playing days has become one.

Followed by a devastating segment in which Goldberg finds out Dykstra is, well…

GOLDBERG: You don’t read books because they might hurt your batting eye?

DYKSTRA: Yeah. Them little words? Plus it makes you think too much. It’s too confusing. I just don’t like to read.

You’d think that would give a reporter, um, pause.

As Stewart says (with the benefit of hindsight, of course, but I mean—really): “Who better to trust your investment portfolio to than a not-so-literate horseshit-chomping man named Nails?”

But Goldberg isn’t alone in looking bad here, and at least he has gone back for another report on the mess Dykstra has made. I haven’t seen anything yet from Fortune, the New Yorker or Jim Cramer and TheStreet.com, each of whom looks equally as bad or worse. Because Nails has proven brittle since these reports aired.

Dykstra got a fawning six-page writeup in Fortune in December 2006 headlined “How He Nails the Market.”

Fortune allowed Dykstra to claim, without any apparent fact-checking, that 95 percent of his options tips made money, which sounds implausible on its face.

Which brings us to CNBC house clown Jim Cramer. Dykstra made those options tips in a $1,000-a-year newsletter for Cramer’s TheStreet.com called “Nails on the Numbers” for which he earned $1 million a year, according to the New York Post.

Cramer was all-too-eager to hype Dykstra’s investing “prowess,” as the Daily Show clip shows, excruciatingly, with a clip of Goldberg interviewing Cramer on the set of CNBC’s Mad Money:

I think people don’t think of Lenny as sophisticated. But I am telling you, Bernie, he is not only sophisticated, but he is one of the great ones in this business. He’s one of the great ones.

Interestingly enough, Forbes, which as far as I can tell was the first major publication to raise questions about Dykstra, wrote in June of last year that he had odd connections to a former TheStreet.com writer:

Yet a close look at Dykstra’s portfolio raises doubts about whether the baseball All-Star turned TheStreet.com guru has been picking many of those stocks or relying on a seasoned stand-in.

Forbes found this in a lawsuit by publisher Doubledown:

There, Doubledown claims, “At Dykstra’s insistence, Doubledown began negotiations to pay Richard Suttmeier, a stock analyst, to provide Dykstra with research assistance for the Dykstra Report and who, upon information and belief learned subsequently, provided Dykstra lists of recommended stocks daily.”

Who is Richard Suttmeier? A market strategist for financial Web site RightSide Advisors and formerly a contributor to RealMoney.com, a subscription Web site owned by TheStreet.com.

And:

Dykstra, who speaks in a slow drawl and now sports a hefty paunch, likewise denies that Suttmeier is picking his stocks. “It’s a bald-faced lie. Not even close,” he says during a brief interview.

Not even close? FORBES compared Dykstra’s buy recommendations as they appeared on TheStreet.com from Apr. 1 through May 1 with those in Suttmeier’s weekly Sector Report during the same month and before. Among Dykstra’s 17 buys, 11 had appeared days earlier in Suttmeier’s newsletter.

A retroactive tip of the hat is due Forbes here for applying a little reporterly skepticism to a story that seemed too good to be true. Even the New Yorker got taken in by Dykstra, writing an amusing but credulous profile in March 2008, a big time in the press for Dykstra, who apparently made a big PR push for a magazine he was launching.

The New Yorker, which titled its piece “Nails Never Fails:
Baseball’s most improbable post-career success story,” bought the apparently false assertion that Dykstra owned his own Gulfstream jet.

Ryan Chittum is a former Wall Street Journal reporter, and deputy editor of The Audit, CJR's business section. If you see notable business journalism, give him a heads-up at rc2538@columbia.edu. Follow him on Twitter at @ryanchittum.