One of the most important — yet most difficult — things for an attorney to do in private practice is to advise a valuable client not to do something that the client really wants to do. As Jeffrey Toobin brilliantly relates in this New Yorker article on the downfall and trial of Martha Stewart, that dilemma was one of the primary reasons that Ms. Stewart’s case went awry. Mr. Toobin details the questionable representation that Ms. Stewart received from Wachtell Lipton during, and in preparation for, her initial interview with the Justice Department, and the disastrous effects of her co-defendant attorney’s cross-examination of the prosecution’s main witness during trial:

On the scale of highly publicized misdeeds in the past decade, Stewart’s trade must rank among the most trivial. She netted only about fifty thousand dollars more on the deal than if she’d held the stock for another day, and, as she told me, her ImClone holding constituted .03 per cent of her assets. It seems almost implausible that such a misstep could send Stewart to prison and lead her company to ruin, and that this happened with the help of the best and most loyal people that money could buy.
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On February 4th, . . . [Wachtell Lipton partner John] Savarese and an inexperienced associate at Wachtell, Lipton accompanied Stewart to her interview at the U.S. Attorney’s office in Manhattan. Confident that she could truthfully refute the charge that Waksal himself had tipped her, Stewart told investigators the fabricated story about the pre-existing agreement to sell ImClone at sixty. Worse, Savarese allowed a second interrogation, on April 10th, during which Stewart again lied about the sixty-dollar agreement and asserted, falsely, that she couldn’t remember whether she was told on December 27th that the Waksals were selling. To be sure, it was Stewart, not her lawyer, who lied to the investigators, but Savarese had allowed his client to take an immense legal risk
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Through the early part of the trial, Peter Bacanovic’s lawyers generally deferred to Morvillo, much as their client did to Stewart. Bacanovic’s lead lawyer, Richard Strassberg, a former Assistant U.S. Attorney in Manhattan, who is now with the firm of Goodwin Procter, presented Bacanovic’s opening statement, but he shared substantial responsibility for the defense with David Apfel, a Boston-based partner at the firm. Apfel, who is fifty-one, had a distinguished career as a federal prosecutor in Massachusetts, where in 1997 he won the John Marshall Award, the Justice Department’s highest award for trial work. In the late nineties, he turned to private practice, and, at the lectern on February 4th, he proceeded to give life to the courtroom adage that the best prosecutors do not always make the best defense lawyers.
Apfel organized his notes, stared down Faneuil on the witness stand, and snarled at him, “Mr. Faneuil, let’s get a few things straight right away.”
Thus began a catastrophically ineffective cross-examination. . .

I continue to agree with Professor Bainbridge that prosecutorial discretion should have mitigated against a prosecution of Ms. Stewart in this case. But as this article points out, Ms. Stewart and her advisers’ failure to address her actions in selling the ImClone stock in a forthright and honest manner bears much of the responsibility for Martha’s demise.
Thanks to Evan Shaeffer for the link to the New Yorker article.