Joe Gregory was a top Lehman executive, known as one of Lehman’s "Huntington Mafia." In 2007, he set his sight on overtaking Goldman Sachs. In StockJockey’s view, Gregory’s pushing employees to meet his competitive targets, requiring upping the leverage and taking greater risks, were key in Lehman’s ultimate demise. 
How Joe Gregory Ruined America
Of all the mistakes I have made over the last year, defending a thesis that Lehman Brothers would probably survive was the worst. Did Erin Callan lie? Sure, but she was a CFO, and that is her job.
I have been surrounded by hedge fund managers for a long time – before David Einhorn started Greenlight, in any case. And while he had a solid thesis, I thought he had to be exaggerating certain aspects – that is his job. And I thought Lehman management could take steps to stave off the worst case scenario, and emerge as it looked circa 2000.
Monetizing Neuberger & Berman was part of it; that ongoing soap opera just ended as the existing management and employees assumed control, and attempt to right the ship. No doubt it was the only option they would consider – even a generous compensation retention plan might not have appealed to Neuberger employees, who probably had more fun with bankers than Ken Lewis. And had seen enough.
But I would have been a bit less skeptical of Lehman’s eventual demise had I known about the hijinks surround Dick Fuld’s top lieutenants, aka the "Huntington Mafia":
Like Fuld, Gregory started on the commercial-paper trading desk. By the 1980s he’d become a top executive in fixed income and was known as one of Lehman’s Huntington Mafia, because all four executives in it lived in or near that North Shore town and often commuted together. “It was said that the four of them decided the fate of the floor every day on their drives back and forth,” recalls one ex-colleague. “And you had to be in their good graces to survive on the fixed-income floor.” Vanity Fair
Gregory was the worst kind of Wall Street pond scum – the hatchet man for a boss whose ass got kissed near daily.
And while Gregory was generous with charitable donations, it was probably just another reason to throw money around: 
Tired of the 90-minute commute, Joe bought a helicopter for the ride. When he realized the chopper couldn’t fly to Manhattan in inclement weather, he got a seaplane. Niki was known as the best customer at the high-end boutique where all the wealthy North Shore wives shopped; the store’s personal buyers came to the house, their arms filled with couture and cashmere. The Gregorys undertook a renovation of the Lloyd Harbor home that would cost, by one report, $3.5 million. They bought the Bridgehampton home for about $19 million in 2006 and hired a top local designer to do it up. One day Gregory called his staff out to admire the new Bentley he’d just bought for his wife. “Look at the dashboard,” he allegedly said. “It’s one piece of burled wood.”
By the end of 2006 Gregory was pushing Lehman employees to the brink, chasing new goals that ultimately doomed the firm.
At Lehman, Gregory set a new goal in 2007, according to a former colleague: he wanted Lehman to overtake Goldman Sachs, which was raking in huge profits by leveraging as much as 40 to 1. And he wanted Lehman’s share price to reach $100. He imposed ambitious targets on all of Lehman’s capital departments, targets that required taking big risks on deals that would become increasingly shaky.
As the real-estate market collapsed, so did those investments. For Gregory, the end came in June 2008, with the release of Lehman’s shockingly bad second-quarter numbers: $2.8 billion in losses, after months of confident pronouncements from the firm.
While there was more than one cook in Lehman’s kitchen, his inexplicable behavior to buy shit (cars, homes, helicopters etc) and spend money like a drunken sailor might make him patient zero in the plague that now infests the Globe.
While that might be a bit harsh of a judgment, Joe Gregory clearly lost his bearings, and connection to the real world, years ago.
You have to live in NYC, and work at a bank or asset manager to really understand how this can happen – and it certainly does not play in Peoria. 
Throw this article in the time capsule, it pretty much says it all.
God damn bankers!
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Profiles in Panic
Vanity Fair
What it Costs
New York Social Diary
