Time was, hedge fund manager Raj Rajaratnam and McKinsey director Rajat Gupta were great pals. Maybe not the kind that asked each other to serve as godfathers to their children, but certainly the kind that could be dubbed "Work BFFs." The sort that would IM each other Monday morning to chat about what they'd gotten into that weekend, play in the same fantasy football league, and pass on inside information obtained during confidential board meetings from which the other could profit. And while onlookers to the bosom buddies might've hoped their bond could survive both men being convicted on securities fraud chargers and sent to a prison where inmates are sent to solitary confinement for being caught with an extra pillow, the Times reports that, shockingly, such is not the case.

Friends, a former inmate and those who have interacted extensively with the two men describe what has become an awkward relationship. The two lead parallel lives that sometimes intersect. They occasionally run into each other in the common areas at Devens and exchange pleasantries. Although both men are in prison for the same crime, their friendship is irrevocably broken.

It's upsetting to say the least, but is there any glimmer of hope? A small chance that one day, in the near future, the two could bury the hatchet and team up to work the prison system like they worked Goldman Sachs? Not bloody likely. Especially considering Gupta has been seen running around with a replacement Raj.

Before his recent transfer to the main compound, Mr. Gupta reported daily at 5:30 a.m. to the cafeteria, where he washed tables. He liked to take a brisk five-mile walk before the 8:40 a.m. inmate count, Mr. Morgan said. After dinner at 4 p.m., the two walked and talked. “Those conversations were priceless,” Mr. Morgan said. “Where would I ever meet a guy like Rajat?” The two men played handball and racquetball and were champion bridge partners. “He is the most competitive man. Don’t let anyone tell you differently,” Mr. Morgan said. “When we played cards together, we won. Whatever he does, he played to win.” In the summer on Thursdays, the two split a pint of ice cream from the commissary.

Obviously things are already strained between Gupta and Rajaratnam as is but Gupta just better pray none of those pints were Coffee, Coffee, Buzz Buzz or it'll be on.

Onetime Allies on Wall Street Have Uneasy Prison Reunion After Insider Trading Trials [Dealbook]