Be careful how you choose your legal metaphors. Bypassing banal comparisons of litigation with war, New York lawyer Judd Burstein invoked medicine in an ultimatum to a law firm he was about to sue on behalf of its former client. To his nearly instant, and now surely his eternal, regret, Burstein urged the firm to settle or face “the legal equivalent of a proctology exam on your finances and billing practices,” which, Burstein emphasized, he had no “desire to conduct” but “will not hesitate to do.”

Bad move. Last May, citing the proctology letter and other conduct, Manhattan federal judge Denny Chin ordered Burstein to explain why he should not be sanctioned. Then, in November, Judge Chin ordered Burstein to pay the defendant $50,000 to offset the cost of its successful defense. (The firm also won $670,000 in legal fees on its counterclaim.) The court relied on its “inherent power” and on a statute that permits sanctions when, in “subjective bad faith,” an attorney “multiplies the proceedings … unreasonably and vexatiously.” Burstein has appealed.

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