Jay P. Lefkowitz ’87

Ever Ready

Spring 2012

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Jay P. Lefkowitz ’87 believes in the power of being well prepared. The senior litigation partner at Kirkland & Ellis regularly readies for appellate arguments by asking his three-person team to compose 25 tough questions that he might be asked by judges. Lefkowitz writes out answers to each question. Then his colleagues propose three follow-up questions to each of his answers, and Lefkowitz prepares responses. That makes for 100 questions—for every court appearance.

“I developed that habit from presidential briefings,” says Lefkowitz, who served as a White House adviser during both Bush administrations. “I prepared for each briefing the same way: By asking myself what are the 20 questions the president will ask me, and what might his follow-up questions be. There’s nothing more precious than the president’s time.”

Lefkowitz’s work for George W. Bush made a lasting impression, and, in 2005, after serving as a White House lawyer and senior policy adviser, the president appointed him U.S. Special Envoy for Human Rights in North Korea.

Recently, Lefkowitz, who is also an adjunct professor at Columbia Law School, drew from his experience in both the private and public sectors to successfully argue a case before the U.S. Supreme Court. The case dealt with the preemption of state lawsuits challenging the adequacy of generic drug labels, which are regulated by federal law. To prepare, Lefkowitz bolstered his normal preparations with seven mock oral arguments before colleagues and co-counsel, as well as a three-hour session before a group of seven Columbia Law School professors. Lefkowitz was grateful for the additional grilling, explaining, “You can never prepare enough.”

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Photographed by Rohanna Mertens