No CEO Wants to Deal With Prison … but Here’s How

By Carlos Gonzalez

The photographs were haunting.

R. Allen Stanford, the once wealthy and powerful financier, now sat chained to a hospital gurney. The victim of a jailhouse fight, Stanford looked at the camera through swelling eyes and a bloodied face.

This is prison in its starkest form.

A place ruled by a code of conduct that is unknown to most in the outside world. Inmates lose control over every aspect of their lives — from what they eat, to when they can take a shower, to whether they can use the telephone. Indeed, it was Stanford’s use of the telephone and the annoyance it caused a fellow inmate that apparently resulted in his violent encounter.

Even the prospect of facing jail time is a nightmare — and for hard-charging executives who are used to calling the shots, the routine, violence and pettiness that characterizes prison life can be difficult to prepare for, much less accept.

Although not every aspect of prison life can be controlled, there are certain steps that executives can take to prepare themselves to confront this harsh system. This article offers guidance both for top executives facing jail time — and those who have just arrived behind bars.

Before Incarceration

Executives under investigation or indictment rarely want to speak about incarceration. To talk about prison means that they have lost; that they are in fact “guilty” of the crimes charged by the government. And yet, in many cases, especially federal white-collar prosecutions, the prospect of prison becomes almost inevitable.

Absent a verdict of “not guilty,” federal cases are now charged in such a manner that extensive prison time will follow a conviction. This “piling on” of charges is done to force a guilty plea that many defendants accept, hoping to cut their losses and win a reduced sentence. In the vast majority of cases, a plea of guilty will carry with it a prison term.

Preparing for prison is a three-step process. There is the mental, the physical and the legal.

Mind Games

A person facing prison time must begin training their mind to accept the highly regimented lifestyle of prison life. Inmates are micromanaged. If they are lucky, the prison guards that oversee them will be decent and will not abuse their power.

Yet, even in those cases where prison guards and officials are not focused on making inmates’ lives more difficult, prison life will pose a significant psychological challenge. Boredom will set in, the pettiness of the many rules will begin to frustrate, and the general lack of freedom will result in stress.

Experience has demonstrated that psychologists and other mental health professionals play an important role in helping executives prepare for prison. These professionals teach prospective inmates to think differently about their situation, to adjust their expectations, and to develop the coping skills necessary for the very unique aspects of prison life.

Get Physical

Incarceration also takes a physical toll on people. It is important to stay healthy — even before entering prison. The change in routine and food, not to mention the stress of incarceration, will affect the body significantly.

Executives who have always exercised should continue to do so before they enter the prison system. For those who have not previously exercised, they should develop a program they can sustain while behind bars.

Money Matters

Finally, there are the legal issues to address before entering prison. Anyone contemplating even a short term in prison should make sure that their affairs are in order.

Investments, including real-property and other assets should be safeguarded; debts should be managed; and any other continuing obligations addressed. Working with a lawyer, accountant, and other financial professionals will ensure that the executive’s affairs are in order. Although executives will not be isolated from the outside world while in prison, it is not as easy to meet and discuss sensitive, personal matters while incarcerated.

Surviving Inside

Settling into prison will be a challenge. Prison is boring. Staying safe will be a priority. The executive who is used to running in a small circle of very similarly minded people will be exposed to a significantly more diverse crowd behind bars.

Opportunists abound.

To be safe, executives should keep a low profile, measure their words carefully and never disclose details regarding their personal lives or cases. The key will be to develop a routine.

One executive I represented years ago became a voracious reader. He read dozens of books, in addition to a steady stream of newspapers and magazines. As he explained it to me, the news, in particular, helped him stay connected to the outside world.

Other inmates work (when possible), or develop exercise routines, all with the goal of keeping both their minds and bodies healthy.

One More Challenge to Be Mastered

Urging a federal judge to release their client on bond, Allen Stanford’s attorneys wrote in 2010 that “nearly one year in detention later, Mr. Stanford’s incarceration has reduced him to a wreck of a man … .” The lawyers explained that Mr. Stanford “experienced … a precipitate, severe and ongoing deterioration of his mental and emotional health caused by the conditions of his confinement.’

Prison is a difficult place, but it is one that can be managed.

Successful executives have overcome significant challenges during the course of their careers. When viewed in the best light possible, prison is but one more challenge to be mastered and ultimately overcome.

Carlos F. Gonzalez, a partner at Miami-based Diaz Reus & Targ, LLP, is a trial and appellate lawyer who concentrates his practice on civil, commercial, and criminal defense matters.
Originally published: Sep 11, 2011

Leave a Reply

Your email address will not be published. Required fields are marked *