The legendary M&A heavyweight has spent the last decade attempting to imbue his firm with his encyclopedic deal know-how. It just might have worked.

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When Bob Greenhill announced last October that he was stepping down as CEO of the firm he had founded in 1996, hardly anyone noticed. The news, mostly ignored by the media, was buried in a company press release on third-quarter earnings. The markets passed over it as if it were just another personnel shift; Greenhill's NYSE-listed shares traded nearly flat that day.

Internally, reaction was even more muted. Greenhill himself had composed a memo on the subject, e-mailing it to his workforce of 220 -- though to this day he has trouble explaining exactly why he made the decision when he did, other than to say that it was "the appropriate time," and necessary to make the firm's succession plans clear. There was no triggering event -- no health problem, no sudden impulse to retire and live out the rest of his days in ease with the massive fortune he had amassed by taking his firm public in 2004. Greenhill, in fact, said he still intended, as the company's chairman, to help execute deals pretty much as he always had.

In some ways, the shift was purely titular. Day-to-day management of the M&A advisory shop had, effectively, been the responsibility of co-presidents Scott Bok and Simon Borrows since before Greenhill's IPO. (Both men -- Bok is head of the U.S. office; Borrows, a Brit, heads the London outpost -- were promoted to co-CEO when their boss stepped upstairs.)

But in other ways, the shift was a nod to the inevitable. Greenhill, who turned 72 in June, is at the twilight of a celebrated Wall Street career (see Alpha Tale) that has spanned more than five decades, starting in 1962, when he landed a job as an associate at Morgan Stanley out of Harvard Business School. He's the kind of banker whose name always comes coupled with references to his Rolodex, that hoary metaphor for the possession of close relationships inside corporate America's most posh executive suites.

Known for the loyalty he inspires in clients, Greenhill built his firm on these relationships and his subsequent reputation as an adviser to titans, and although other legendary dealmakers have left white-shoe firms to strike out on their own, few have found as much success as Greenhill in so short a time (or so late in life): His company boasts a market cap of about £800 million, 2007 revenue of £200 million and a stable profit margin of 40 percent.

"Greenie has as good a Rolodex as anybody I've ever met," says Tom Hicks, a longtime friend and client. "But he doesn't just know a lot of people; people trust him." And yet, of course, there will come a time when Greenhill’s presence at his firm will come to an end -- which raises the obvious question: What happens to Greenhill & Co., still in its adolescence, when its chief executive is gone?

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