Going to Prison? You Might Need a Little Advice

Martha Stewart Hires a Consultant To Help Her Adjust

Before reporting to prison, every smart white-collar criminal knows what to do: hire a consultant.

There are so many details to work out -- being sent to the cushiest possible jail, handing over control of personal finances, coping with the psychic shock sure to set in when the cell door bangs shut and freedom, even if for just a few months, is snatched away.

Martha Stewart, sentenced on Friday to five months in prison for lying to federal agents about a stock sale, has one of the best-known consultants in the business in Herbert J. Hoelter.

Hoelter, who has helped such people as financier Michael Milken and Sotheby's chairman A. Alfred Taubman adjust to prison life, said in an interview that the biggest challenge often is making formerly powerful clients understand that Bureau of Prisons rules do not allow them to conduct business from prison and that their contact with the outside world will be severely restricted.

The message doesn't always get through.

Hoelter said a client in California recently got tossed into solitary confinement after guards caught him trying to sign some closing papers he'd been sent for a real estate sale. Another lawyer said one of his Wall Street clients demanded to know what his e-mail address would be in jail. Inmates cannot use e-mail.

"The transition from being outside to being an inmate is a dramatic one," said Hoelter, who runs the National Center on Institutions and Alternatives in Baltimore.

Stewart, has already taken care of a major real estate deal, selling a luxury apartment in Manhattan. Over the past few weeks, she has also sold several million dollars worth of stock in the company she founded, Martha Stewart Living Omnimedia Inc. But, as other white-collar criminals have found, there are other matters to consider.

In 2002, weeks before he was set to report to a federal prison camp in Florida to serve a 41-month sentence for fraud, shoe designer Steve Madden decided to take care of a few painful loose ends: his teeth.

Madden's lawyer petitioned a judge for a short delay in the start of his sentence so he could get a root canal, fill some cavities and have surgery to fix a deviated septum.

"Every lawyer who has a client on his way to a federal institution should advise his client to take care of all his dental and medical needs before they get there so they won't have to resort to care from people they don't know, and it's probably substandard care," said Joel Winograd, a New York-based lawyer for Madden.

Winograd said Madden's business has continued to do well because Madden arranged for a good team to run things in his absence. "The company is bigger than any one person -- same with Martha Stewart," Winograd said.

Beyond personal and financial matters, consultants and lawyers strongly recommend that prison-bound former executives prepare themselves psychologically.

Sentencing consultant David Novak, who served a year in prison on a mail-fraud charge, said that applies to Stewart despite her tough talk outside the courthouse on Friday about not being afraid.