Barons of the Big Deal


assignment right or the project right or you did the analysis correctly or you did the trade correctly, or you didn’t,” he says. “Wall Street, I believe, comes the closest to being a meritocracy, where at the end of the day, by and large, people are evaluated and rewarded based on merit.”

There’s no doubt that Lewis rose to the top on his merits. “He has knowledge of the financial markets, finance, and transactions to the extreme. He’s extremely knowledgeable — among the top in the country of all the appropriate financing techniques and advice for executives and their corporate entities,” says George Van Amson, managing director of institutional equities at Morgan Stanley.

Lewis joined Morgan Stanley as a financial analyst in 1978. After taking a break to get his M.B.A. from Harvard, he returned to Morgan Stanley as an associate in 1982. By 1989 he was elected a managing director, becoming the first African American to do so. Between 1994 and 2004, Lewis was head or co-head of each of Morgan Stanley’s origination and execution businesses.

Though Lewis is as personable and charming as you might expect of a Southern gentleman, don’t let the cool demeanor fool you. One has to be competitive to succeed in this business, and Lewis is no exception. Brian Leftwich, vice president of investment banking at Merrill Lynch, recalls the first time he played golf with Lewis in South Hampton, New York, years ago. At the time, the young associate was nervous about playing golf with his boss. Leftwich wanted to make a good impression, so he woke up at 5:00 a.m., giving him plenty of time to make the 8:00 a.m. tee time. But he got lost, was five minutes late and arrived just in time to see Lewis ready to tee off without him. “He paired me up with somebody else. I proceeded to shoot a 71, which is a really low round.” Once Lewis found out what a solid golfer Leftwich was, he partnered with him on the course the following day. “So, he had no problem pushing me off on someone else, until he found out how good I was. Then he said, ‘You’ll be with me, we’ll play them tomorrow.'”

MCGUIRE: THE SCIENCE OF THE DEAL
For McGuire, it’s not the size of the deal that matters. He gives the same energy and level of analysis to deals in the millions as he would for those in the billions. “You know, he’s an M.B.A. and a J.D.,” points out Baldwin. “So he picks a deal apart from both sides — the business side and the legal side — and that’s what gives him the edge.”

McGuire received his B.A., cum laude, from Harvard College in 1979 and his M.B.A. and J.D. from Harvard Business School and Harvard Law School, respectively, in 1984. His career on Wall Street began that same year in the mergers and acquisitions group of First Boston Corp. When top officers Bruce Wasserstein and Joseph R. Perella left First Boston in 1988 to start


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