Sentence Mitigation Case Study 

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In our first three modules, we’ve given you the theory behind our Prison Professors’ Sentence Mitigation Program. That theory urges our clients to begin with a clear understanding of the best outcome. 

To the extent possible, we recommend that participants contemplate the perspective of the stakeholders who will make judgment decisions in the future. 

Obviously, every participant would like to avoid any type of sanction at all. Yet an effective mitigation strategy requires that we live in the world as it exists, and not as we want it to be. We begin from the perspective of stakeholders:

  • What will the judge think of me? 
  • What will the prosecutor think of me?
  • What will the probation officer think of me? 
  • What will people in the Bureau of Prisons think of me? 
  • What challenges will I face from people I meet in the future, after this part of my life is behind me?

If we create a strategy from their perspective, we can take more methodical action steps. 

When federal prosecutors bring charges against a defendant, a record exists. That record can lead to judicial bias. It can lead to bias from others in the system. We must craft our strategy to counter those perceptions. We want to disrupt the image of those who judge our clients. If we prepare an effective mitigation strategy, we can influence the outcome of the hearing. 

The sooner we begin to prepare, the better off we are. 

In these following modules, we work through the mitigation strategy in a practical way. We will take the lessons we’ve learned and apply them. 

When our mitigation experts work on a project, they sometimes create mitigation packages that stretch into multiple volumes. You can see examples of those strategies on, where we feature the work our team completed with leaders such as:

  • Bill McGlashan, one of the world’s leading impact investors
  • Mossimo Giannulli, clothing manufacturer

Both of those people faced challenges from the criminal judicial system. And both of those people created effective mitigation strategies to improve their outcome. They continue their mitigation efforts, working with our team to build solutions to collateral consequences of mass incarceration.

What will you do to work toward your mitigation at every stage of the journey?

The remainder of this lesson offers an example that you may use as a template. We’re offering some salient points to consider in a mitigation strategy. Then we will offer commentary on where we would go if this were an actual mitigation package. We offer some analysis, trying to explain why we wrote such words and what a client may be thinking when preparing a mitigation piece. So as not to betray the confidence of any people that works with our team, I’m using my own story as an example. Below is the abbreviated version of the story that brought me into the criminal justice system.

The Facts:

When I was 20 years old, I saw the movie Scarface. By then I was already going down a bad path. I didn’t think much about making the type of values-based, goal-oriented decisions that our team at Prison Professors teaches now. 

Back then, I chose friends who had a bad influence on me. When I saw Al Pacino playing the character Tony Montana, it looked pretty cool. 

Soon after watching the movie, I began making inquiries about the price of cocaine. I looked for information on how much users would pay for cocaine. And I looked for information on how I could purchase cocaine in sufficient quantities to make a profit. Wanting to limit my exposure to potential problems with the law, I hired other people to handle and transport the cocaine. 

Those decisions exposed me to charges of a more serious nature. A grand jury indicted me. I knew that I was guilty of every count. Yet rather than making decisions that would show an acceptance of responsibility, and express remorse, I pushed prosecutors to the limit. I went through trial. I committed perjury on the witness stand, claiming that I didn’t have anything to do with selling cocaine. 

A jury convicted me of every count. The crime for which I stood convicted carried a possible sentence of life in prison. I was 23 years old. 


At the outset, I was in a worse position than most. I lied on the witness stand. A jury convicted me. I was convicted of serious drug crimes at the start of our nation’s war on drugs. Considering the severity of my crime, and the way I responded, my lawyers suggested that I prepare for the worst. From their perspective, my judge could very well sentence me to life in prison. 

In my case, the conviction truly did bring a shift in mindfulness. In Earning Freedom, I describe the shift. After the jury convicted me, I began to think differently. I realized that I was in serious trouble and I wanted to change. That desire to change led me to begin questioning my past decisions. 

  • What would happen to my life if I remained defiant? 

I had to consider the predicament from my judge’s perspective. My perspective didn’t matter. My judge had the discretion to sentence me to life in prison. 

  • How did he view me? 
  • How would the decisions I made in the past influence my judge’s decision at sentencing? 
  • What was the best possible outcome? 

Regardless of how I felt about the criminal justice system, the fairness of the prosecution, the sentencing system, I needed to consider the questions above. 

  • What, if anything could I do to influence the outcome? 

To start, I needed to influence my judge’s perception. My past decisions likely had a very bad impression on him. Not only did he hear all of the evidence against me, he saw me during the trial. I took the witness stand, put my hand on the Bible and I swore to tell the truth. Then I responded to questions from my attorney by looking at the jury and lying. I denied any involvement in the crime and accused the prosecution of profiling me. 

In retrospect, I could see that the judge likely considered me the worst type of criminal. Despite how I saw myself, in my judge’s eyes, I was a manipulative young man who lacked any sense of remorse. That is the type of defendant that could very well warrant a maximum sentence. 

Considering my conviction, the maximum sentence would be life. 

  • What could I do to mitigate those perceptions? 

Decisions I made in the past were not going to make it simple. Saying “I’m sorry judge” is not effective as a mitigation strategy. Likewise, I wouldn’t get the result I wanted by arguing that a lengthy sentence wasn’t fair.

Preparing for the lowest possible sentence requires us to think differently from the way that we’ve thought in the past. 

Those who’ve gone to trial, as I did, have a particularly difficult task in building a mitigation strategy. It’s difficult, but as readers will find in Earning Freedom, it’s never too early and it’s never too late to sow seeds for a better outcome.

Scott Tucker Example:

Take the case of Scott Tucker. Scott was the founder and CEO of a several companies that generated billions of dollars of revenues, taxes, and profits. The business centered on the payday lending industry. He launched his business more than 20 years ago as a startup and he grew the venture. Over time, his company employed thousands of people. Throughout the development of his company, Scott hired legal counsel to advise him on the decisions he would make. By relying on those letters of opinion from counsel, Scott created a business that he believed operated within the letter of the law. 

Government representatives disagreed. 

During an interview I did with Scott, he told me that he invested more than $1 million each month to pay lawyers that would advise his business on compliance. He battled in state courts across the country. 

When the Federal Trade Commission launched an investigation against his company, Scott’s fortunes took a turn for the worse. A judge ruled in the FTC’s favor and levied a sanction against Scott for more than $1 billion. Then the judge froze his assets. 

Following that decision, prosecutors in the Department of Justice indicted Scott. They accused him of violating the Truth in Lending Act, among other crimes. Without assets, he proceeded through trial with appointed counsel. A jury convicted Scott of all counts. 

Since prosecutors argued that Scott’s business generated “losses” that exceeded several billion dollars, the Federal Sentencing Guidelines recommended a sentence of more than 130 years. Scott’s lawyers said that prosecutors would agree to cap Scott’s sentence at 20 years if Scott would forfeit his appellate rights. 

When Scott began working with our team, the record was already well documented. We couldn’t change the past. Instead, we had to think about steps we could take for the best possible outcome. 

Our approach differed from what Scott wanted to argue in his approach to sentencing. Like many defendants: 

  • Scott disagreed with many of the judge’s rulings throughout the judicial process.
  • Scott thought that the jury did not truly understand the complexities of his business.
  • Scott believed he was not guilty of the crime, and he wanted to express his feelings to the judge. 

We knew that Scott faced many challenges. His businesses generated hundreds of millions in profits for him. Yet his clients were people who needed to borrow a few hundred dollars to make ends meet until their next payday. In the eyes of stakeholders, Scott would not be a sympathetic figure. That was obvious by looking at the length of sentence that both prosecutors and probation officers requested. 

To begin the mitigation strategy, we had to ask a few basic questions. 

  • How would arguments that Scott wanted to make influence the judge?

If Scott tried to litigate the merits of his case during the sentencing hearing, we believed the judge would perceive him as being a poor candidate for mercy. 

  • What strengths did we have going forward?

Despite challenges that follow for anyone who loses after a trial, we knew that the judge did not know anything about Scott personally. Lawyers presented their theories of the case in motions to the judge. And the judge listened to testimony from witnesses. Those factors did not work in Scott’s favor. 

Still, up until we launched the mitigation strategy, the judge would not know anything other than factors of the case that led to Scott’s conviction. 

A mitigation strategy could give the judge a different viewpoint. We had to help the judge see Scott as a human being. In our strategy, we created a package that helped the judge understand more about Scott’s background. 

  • We built a story to humanize Scott and to show the motivations that led him into business. 
  • We helped the judge understand why Scott exercised his right to trial, and then we showed what Scott learned from the entire process. 
  • We emphasized steps Scott was talking to make things right, and to the extent possible, expressed remorse for people who suffered because of his business model. 

We know that strategy led to a sentence that was far less than the 100+ years requested by the government. Prior to Scott’s sentencing date, we filmed a series of videos. Scott spoke about his business, his experience, and about the sentence-mitigation strategy. 

My Mitigation Strategy:

In my case, the mitigation strategy was even more difficult. Besides contesting my guilt through trial, I made matters worse by lying on the witness stand. I said I didn’t have anything to do with selling cocaine. It was part of my scorched-earth defense strategy. Deny everything. After the jury convicted me, I would need to face fallout from my failed strategy. 

Lawyers told me to expect a life sentence. 

I returned to my jail cell in deep thought. I remember lying on my concrete bunk and glaring in a daze at the ceiling. 

  • “What, if anything, could I do to unravel the mess that I created?”

Those thoughts led me to begin thinking about my future. The judge would have a direct influence on my life. He would sentence me. How could I overcome the judicial bias that followed my earlier decisions? Those decisions included: 

  • Selling cocaine.
  • Refusing to accept responsibility.
  • Going to trial.
  • Committing perjury on the stand. 

Without a doubt, those decisions would have left an impression on my judge. I had to think. 

Those thoughts led to action. 

In my case, mitigation efforts would require me to undo some of the damage that I caused. If the judge considered me an unrepentant criminal, I had to ask good questions.

  • What action could I take to reverse his perceptions of me? 

First step, I had to stop thinking about myself. The judge likely thought of me as being a selfish, egotistical person. I was a convicted criminal. The judge would have thought that I didn’t think about anyone but myself. I had to change his thoughts. 

More than changing his thoughts, I needed to show him the work, so he would be able to connect the dots. People don’t make lifelong changes overnight. I would need to show him how and why I made changes. And I would need to make that case in a persuasive way. 

As I wrote in Earning Freedom, Socrates inspired my strategy. By reading about the ancient philosopher, I learned that I needed to think about the broader society. I needed to show that I wanted to live for something that was greater than myself. His story inspired me to act. 


I wrote a letter to Stuart Eskenazi, a journalist who wrote about my trial for the local newspaper. In the letter, I expressed that I regretted my bad decisions. Instead, of accepting responsibility for my bad decisions, I lied about my involvement. 

Members of the jury saw though my lies and convicted me. 

Knowing that I would be going to prison for a lengthy sentence, I pledged to use my time in prison to work toward reconciling with society. If the journalist wanted to learn more, I invited him to visit me in jail so that I could tell him my story. 

Writing to the journalist, for me, would be like drawing a line in the sand. It would show the judge that, despite the bad impression I made by my earlier decisions, I was not beyond redemption. I could do better. I wanted him to see that I aspired to be a part of society—to pay for my crimes in the most responsible way possible. 

The journalist took me up on the offer. He visited me in the jail, and I told him my story. 

Although I didn’t know how long of a sentence my judge would impose, I pledged to use every day of my sentence to improve. I said that I would find a way to make amends for the bad decisions of my youth. 

Writing to the journalist was the first prong of my mitigation strategy. The next step was to write a detailed plan for the judge. That plan included an explanation of what changed for me. He had to see my evolution of thought. Effectively, my earlier decisions left me with the responsibility of persuading someone who would likely be very cynical of anything I said.

So I wrote him a story of how and why I had changed. 

In my case, the change came with stories I read after being exposed to philosophy. I read about Socrates and his response to challenges in his life. By reading about Socrates, I learned more about the art of “Socratic questioning.” I needed to quit thinking about problems that my earlier decisions created. I needed to start thinking about what I could do to make things right. 

Then I detailed a plan for the judge. While I served time in prison, I intended to follow a three-part strategy: 

  1. I would work to earn academic credentials,
  2. I would work to contribute to society in meaningful, measurable ways,
  3. I would work to build a support network.

By detailing how Socrates inspired me to think differently, I could help the judge understand that I shifted my thinking. Then, by taking steps to detail a plan I would follow in prison, I let the judge know that I expected to work through the prison journey. I would work toward becoming a better human being. I would work toward becoming a better citizen. Saying I felt sorry for the crime wouldn’t be enough. I had to take affirmative steps to persuade the judge what I learned through introspection. I had to show that: 

  • I thought about the victims of my crime.
  • I thought about the influences that led to my participation in criminal activity.
  • I thought about steps I could take to show that I wanted to live as a law-abiding citizen.
  • I thought about ways to show the judge that I wanted to make an irreconcilable break from my criminal behavior.
  • I could articulate an actionable plan that would lead to my emerging from prison as a person who was worthy of a second chance at life.
  • I had learned from the entire process.
  • I was worthy of his mercy. 

My judge sentenced me to serve a 45-year prison term. 

Was it what I wanted? 


I did not want to serve a 45-year sentence. But given the bad decisions I had made previously, a 45-year sentence may have been the best, possible outcome. I had a tough judge. And since my attorneys told me to expect a life sentence, I left the courtroom feeling somewhat relieved. At least I had finality. And my mitigation strategy could carry me through the sentence. I would find a way to use the strategy to create a life of meaning and fulfillment while I served the sentence. That strategy would accomplish several goals: 

  1. The mitigation strategy would provide the direction I needed to move through the prison term with a deliberate plan of action.
  2. The mitigation strategy would keep me disciplined and operating with a high level of energy.
  3. The mitigation strategy would allow me to focus on the positive and repel the negative.
  4. The mitigation strategy would get me home at the soonest possible time.
  5. The mitigation strategy would open opportunities for the highest levels of liberty when I returned home.
  6. The mitigation strategy would position me for early termination of my term on Supervised Release.
  7. The mitigation strategy would set me on a path to rebound with career opportunities. 

I am not saying that my strategy is the right strategy for everyone. What I am saying is that once I took matters into my own hands, I stopped the feeling of helplessness. I no longer felt as if I were spinning out of control. I stopped living as if others were going to decide my fate. The strategy restored confidence, put me on a new path. 

It resulted in a 45-year sentence. For me, that was a starting point. I could work from there. It was better than what my attorneys told me to expect. 

Scott Tucker had a similar outcome. He got 16 years. Neither of us got the sentence we wanted. But given our past decisions, it was better than what others expected. 

The time is now to create your mitigation strategy. Figure out an accurate assessment of how the judge and others perceive you. Then work on a plan to show that you are much more than the criminal charge. Show that you’re worthy of mercy. 

Consider the following ten questions. Your responses may guide your personal mitigation strategy.

  1. What does my judge think of me?
  2. How will my prosecutor portray me?
  3. What will my probation officer say about me?
  4. In what ways will my behavior after the conviction differentiate me from other defendants?
  5. Why do I see myself as being worthy of mercy?
  6. What steps have I taken to show what I’ve learned from the conviction?
  7. In what ways have I helped my attorney present a credible case for leniency during my sentencing hearing?
  8. How does my mitigation strategy advance the argument that I’ve got a solid plan to carry me through the prison term?
  9. What was the impetus that changed my mindset?
  10. Why should the judge see me as something more than the decisions that led to my conviction?

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