Get Out of Jail, Not Quite Free

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"My repentance is foremost in my mind in every waking moment and its intensity increases with the passing of every day," writes Leona Helmsley in an uncharacteristically groveling letter to a New York federal judge. The missive goes on to contend that Helmsley, the prominent hotel queen who is serving a four-year sentence for evading $1.2 million in federal income taxes, should be released as soon as possible from the prison in Danbury, Connecticut, where she has been studying for a high school-equivalency diploma. An expected favorable ruling by the judge, perhaps this week, would allow Helmsley to rejoin her ailing billionaire husband Harry and travel, presumably by limousine, to perform 750 hours of community service as a playroom assistant or clerk at a nearby health center.

Helmsley's plea for mercy is a masterly exercise in fawning self-promotion. It includes details of the good works she would do during her parole, newspaper editorials calling for her release, doctors' reports on her allegedly failing health and even letters from well-wishers, including one man who offers to distribute buttons, bumper stickers and lawn signs emblazoned with the words FREE LEONA. It was presented in court by Helmsley's lawyer with the aid of a kind of professional called a sentencing consultant, one of a growing breed of specialists who counsel convicted offenders on how to avoid or cut down on prison time.

Sentencing consultants are poised to be the quintessential post-'80s growth industry. Paul Bilzerian, nabbed for securities fraud and tax evasion, hired one to help him reduce a four-year prison sentence by performing community service at a boys' club. A consultant was instrumental in advising Miami moneyman and convicted tax cheat Victor Posner on his offer to establish shelters for the homeless in lieu of prison time. Onetime Wall Street legal eagle and insider trader Martin Siegel asked for and received the chore of running a children's computer camp. Securities fraudster Michael Milken is awaiting court approval for his plan to educate inner-city youth, a proposal that appears to have contributed to his early release from prison despite an initial 10-year jail sentence.

Celebrity felons may be charged more than $10,000 a case or up to $200 an hour for the services of top-flight sentencing consultants; garden-variety or indigent miscreants are asked to pay far less. Business has been so good at all levels that the consultants have formed their own professional body, the National Association of Sentencing Advocates, with 100 member firms so far. Practitioners, often criminologists or social workers, have found themselves increasingly asked to decipher the compendium of federal sentencing guidelines, which has grown from paperback size to the dimensions of a metropolitan phone book over the past five years.