Bob Greenhill is a Type A's Type A. But throughout his career, that trait has both lifted him up and laid him low. A journey through the adventures – and misadventures – of a dynamic legend.

By his own admission, Bob Greenhill has never had much interest in being a manager, despite having led three investment banks during his celebrated 50-year career. It doesn't appear to be in his nature. A high-functioning charmer, a work-hard-play-hard man about town, a suave exemplar of the rainmaker’s art, he says he finds administrative work dull.

The image he presents is that of a doer -- not a talker or a bean counter or a bureaucrat -- and the tales that make up the anthology of his legend bolster that depiction. He got his pilot's license in his fifties for the express purpose of throttling up a jet and zooming to far-flung meetings with his corporate-titan clients. "He flies like he lives," says one former employee. "Full speed, all the time." His idea of kicking back is heliskiing, or motorcycling, or canoeing above the Arctic Circle with old explorers' journals as his only guides. His favorite retreat is a house in the Maine woods, without electricity or phone lines, from which he once had to snowmobile 15 miles into cellphone range so he could talk to Tom Hicks, a client, who was on the verge of buying $1.5 billion in radio assets from Sumner Redstone (another old client).

You get the feeling that Bob Greenhill is the kind of swashbuckling deal maven with a personality too large, too Type A, for the drab rooms where tedious things like budget meetings occur. His appearance lends that impression: He wears suspenders like an admiral wears epaulets. He has backswept auburn hair, a ruddy complexion that bespeaks quality tee times at exclusive country clubs and a smooth, contagious, easy-money laugh, with which he punctuates conversations like an old gambler on a hot streak. In some lights he resembles Jackie Mason. In others, the actor Albert Finney.

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