[ by Melanie Gretchen ]

Joseph Gregory was a lifer.  He joined Lehman Brothers in 1984, and rose to number 2 to CEO and chairman Richard Fuld.  As president and COO of the Wall Street firm, he had in his possession an estate on Long Island's North shore, a helicopter to ferry him to and from work, a Bentley, and $4.4 million Park Avenue apartment.  In 2007, he and his wife bought a $19 million mansion in Bridgehampton, spent millions redesigning it from top to bottom, and hired a staff of 29 to keep up the oceanfront property.

How the Mighty Have Fallen. Since then, life has not been so rosy.  In 2008, Mr. Gregory was forced to resign amid pressure from several members of his own executive committee over the investment bank’s deteriorating financial health.  That same year, the firm, which made possible his $15 million a year expenses, filed for bankruptcy.

We don't know what he has now, but he hasn't worked in the industry since his dismissal in 2008, FINRA records show, which may be why the unwinding has taken a swift course.  After failing to sell the 9,500-square-foot Bridgehampton home for $32.5 million in 2008 – which the couple reportedly spent less than a month in before first listing – the couple finally sold it to advertising executive Donny Deutsche in 2011 for $19 million, the amount the couple paid pre-multimillion-dollar renovation.

This year, the former Lehman executive is continues to wind down his glory days with the sale of his Long Island mansion, and that is no small asset.  The 6-bedroom, 8-bathroom house in Lloyd Harbor, NY, has a 15,000-square-foot main house and a 6,000-square-foot guest house.  It was one of several Lehman executive properties on Long Island's North Shore, according to a 2010 article in Vanity Fair.

His wife will have to forgo more than a North Shore vacation.  The private plane, since sold along with the Bentley, was also used to take her on shopping trips to Los Angeles, as encouraged by her husband – but as far as we know, Mr. Gregory hasn't lost her.

Paradise lost, but perhaps all is not lost.

For further details, go to [Dealbook, 7/24/12], [Business Insider, 12/9/08], [Real Deal, 3/17/12], and [Luxist, 2011].