NEW YORK (CNN/Money) -
Martha Stewart will finally be sentenced Friday for lying to investigators about a stock sale that brought little financial gain but heavy losses in terms of stature and -- ultimately it seems likely -- her freedom.
Stewart and former Merrill Lynch broker Peter Bacanovic were convicted March 5 on four felony counts each of obstructing justice and making false statements related to Stewart's suspicious sale of ImClone Systems stock in late 2001.
New York federal judge Miriam Goldman Cedarbaum, who has twice delayed this hearing, will sentence Stewart in the morning, and then Bacanovic in the afternoon.
The two face minimum confinements of between 10 and 16 months apiece. But the ultimate penalty is up to Cedarbaum, who could decide to lock them up for even longer or keep them out of jail altogether.
"This is a lot different than most sentencings, which are usually cut-and-dried," said Kirby Behre, a former federal prosecutor now with Paul, Hastings, Janofsky & Walker. "Here the judge has a huge swatch of possible jail time" from which to choose.
Legal experts were split on how hard Cedarbaum would come down, but almost everyone agrees that the sentence will call for some jail time.
"I don't think there's any question that there will be a prison component," said Jacob Frenkel, a former federal prosecutor and Securities and Exchange Commission lawyer now in private practice in Washington, D.C.
Some say the sentence could be as little as five months, but Frenkel thinks Cedarbaum will start with a minimum of a year.
"This is not somebody who made some inadvertent false statement," said Frenkel. Noting Stewart's high public profile, Frenkel added, "this is a case where a jury convicted a CEO for lying to two different government agencies. That's a big deal."
Whatever their sentences, neither Stewart nor Bacanovic will be immediately handcuffed and sent to prison.
Instead, lawyers for both are expected to ask Cedarbaum to allow them to remain out of jail pending the outcome of any appeals. If Cedarbaum denies that request, Stewart and Bacanovic still can appeal to a higher court for a stay of their sentences.
No Mercy?
Stewart's lawyers have submitted papers, kept under seal because they contain detailed confidential information about Stewart, that argue for lenience. Grounds for this request include Stewart's history of charitable giving and the likelihood that Martha Stewart Living Omnimedia, her namesake company, would further deteriorate in her absence.
In addition, Stewart, who did not testify at her trial, has the option of addressing the court at her sentencing hearing.
Stanley Twardy Jr., a former U.S. Attorney in Connecticut, thinks it's unlikely that Stewart will speak to Cedarbaum.
"[Martha] has herself in a Catch-22. If she gets up and says 'I didn't do anything wrong,' the judge could go with 16 months" because Stewart hasn't expressed remorse. "If Stewart says 'I'm sorry,' that undercuts her appeal. She's admitted she's done something wrong."
So far Stewart and Bacanovic have failed to sway Cedarbaum in two separate bids to win a new trial. The first, made soon after they were convicted, argued that a juror, Chappell Hartridge, lied about his past during pre-trial screening.
The second defeat came after federal prosecutors accused one of their witnesses, Secret Service laboratory director Larry Stewart (no relation to Martha), of lying on the stand.
Assuming Cedarbaum does not go easy on Stewart, life for the fallen queen of domesticity is likely to get worse before it gets better.
Where Stewart ultimately does time is up to the Federal Bureau of Prisons. Legal experts say she's likely to be shipped to the same minimum-security lockup in Danbury, Connecticut where hotelier Leona Helmsley did time for tax evasion.
Or, the feds could assign her to a prison with conditions that are considerably more harsh than the so-called "prison camps" where white-collar criminals typically go.
That's what happened to Lea Fastow, an ex-Enron official and wife of former Enron chief financial officer Andrew Fastow, who on Monday was sent to a federal lockup in Houston. She is serving a one-year sentence for tax evasion.
For all the uncertainty that still surrounds Stewart's future, this much is for certain: Prison is not some cushy "Club Fed."
Daily life behind bars, even in a minimum security facility, is highly structured and full of reminders that freedom is a lost privilege. Stewart will wear prison-issue khaki garb, bath in communal showers, and work for a maximum of 40 cents an hour.
That's a far cry from the $673 an hour she earned last year as CEO of Martha Stewart Living Omnimedia (assuming a 40-hour workweek and her $1.4 million salary and bonus).
"For a CEO to be told when to get up, when to eat, where to stand and what to wear, this is a significant punishment," said Frenkel, the former prosecutor.
And, in a bittersweet coda to the saga that began more than two years ago, consider this: ImClone stock closed yesterday at $80.27 a share, up from the average $58.43 that Stewart got when she dumped her shares, reaping about $228,000.
Had Martha Stewart simply held onto her ImClone stock, that investment would now be worth $315,300.
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