What to Know Before Sentencing: 

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At Prison Professors, we offer instructional material to help individuals at different stages of both government investigations and criminal justice proceedings. With such a broad array of topics to cover, we break the information into several sections.

Since there is a considerable amount to learn, I’ve broken this article up into several sections. Follow the subheadings below to get what is most relevant to you, depending upon your given stage of the journey:

  • Section 1: Judicial Proceedings
  • Section 2: Overview of the Judicial Process
  • Section 3: Understanding Sentencing Mitigation

My name is Michael Santos and for those who don’t know, I was in prison for 26 years. I served time in prisons of every security level. That information is relevant for a couple of reasons:

  1. I want readers to know the perspective from which I’m offering this information, and
  2. I want readers to know that I’m not dispensing legal advice.

If you’re facing a challenge with the criminal justice system, you’ll likely rely upon a lawyer. Although I am hopeful that most lawyers will be honest and helpful to their clients, I hired a lawyer that did not advise me well. I would have liked to have learned lessons from people that had gone through the system and emerged successfully.

At Prison Professors our team is hopeful of helping people make better, more informed decisions. We offer books, articles, and self-directed courses that people can use to prepare for better outcomes at sentencing. For those who want to see our books and courses, please click here. Those who want free information will find value in the sections below.

Section 1: Judicial Proceedings

What do you need to know if you become the target of a criminal investigation?

Our answer to the first question is simple: A lot!

Many people that face law-enforcement challenges make decisions that exacerbate their problems. They don’t mean to worsen their troubles by not preparing for court. Yet if they don’t understand what’s coming, what options they have, or where to turn for information that will help them make better decisions, they’re vulnerable.

Targets of both civil and criminal investigations can unwittingly talk themselves into a criminal indictment. They may eliminate opportunities for a diversion from prosecution. Or they may expose themselves to more stringent sanctions.

Competent legal counsel is essential. If a person doesn’t have any experience, a primer on the system may be of help, too. With more knowledge, a non-specialist will feel more competent as he interacts with a criminal lawyer. Without experience, a person will always feel as if he’s operating from a position of darkness, never knowing what’s around the next turn.

Preparing for Court:

By learning about the criminal justice system, a person can arm himself to work more effectively with lawyers. He may understand how to resolve complex dilemmas better. Although the target of a criminal investigation may not like the limited choices available, he may feel more confident that he is going to make the best possible choice. When a person understands context, opportunity costs, and ramifications that follow each decision, that person empowers himself.

We can paraphrase an old Chinese proverb:

  • If you want to know the road ahead, ask someone that has come back.

When under the spotlight of a criminal investigation, it makes a great deal of sense to invest time and energy to learn. By learning, a person can make more informed decisions. Operating without knowledge makes us feel as if we’re hanging from a string as if we’re marionette puppets. To stop that helpless feeling and restore confidence, we need to learn; then, we need to make deliberate decisions that will influence best-possible outcomes.

Acquiring knowledge and becoming more literate about the system is the first step. As the cliché holds, the greatest fear is the fear of the unknown.

Learning from our team at Prison Professors is a great place to start.

Defendants learn quickly that problems with the criminal justice system can lead to enormous costs. It isn’t only money that’s at stake. Liberty is at stake. Future earning power is at stake. Collateral consequences—like access to banking, housing, career opportunities—can linger for a lifetime. Don’t take our word for it. Easily verifiable statistics show the fallout for those who have been targeted by the criminal justice system.

It’s crucial to prepare, and it makes a great deal of sense to learn.

The learning process begins with the reality that many people get sucked into the criminal justice system. Although going through the system is difficult, there are best-practice ways to prepare.

According to a 2019 report by the Prison Policy Initiative, the American criminal justice system holds almost 2.3 million people in the following locations:

  • 1,719 state prisons,
  • 109 federal prisons,
  • 1,772 juvenile correctional facilities,
  • 3,163 local jails, and

80 Indian Country jails as well as in military prisons, immigration detention facilities, civil commitment centers, state psychiatric hospitals, and prisons in the U.S. territories.

Not everyone that goes into the system gets the best outcome. Those that learn more can prepare more. By learning more about the system, people facing criminal charges may put themselves into a different algorithm, framing possibilities for a better outcome. By using excellent critical thinking skills, targets or defendants may influence decision-makers to view them through a different lens, as if they’re fellow human beings rather than cogs that must grind through a criminal justice machine.

All people facing challenges with the criminal justice system share common traits. Their family members, friends, and colleagues care about them. Defendants would like to live in a world where investigators, prosecutors, probation officers, and judges see them as ordinary citizens. Prosecutors may charge people with a crime, but defendants, like all people, have many attributes that are reflective of their character. A crime may be an aberration, a one-time act that is contextual and doesn’t resemble how they would act in most circumstances.

Yet once the criminal justice system targets people for prosecution, stakeholders in the system turn their attention to the alleged criminal wrongdoing. A criminal charge can stop stakeholders from looking at an individual as a human being. In an instant, the person becomes a defendant. The goal or objective is not always justice. It’s a conviction followed by a punitive sanction.

Targets of criminal investigations would like to find some type of diversionary program to avoid prosecution. If they’re prosecuted, they want the best possible outcome. For most people, the best result means the least restrictive or least punitive sanction—preferably a sentence that does not include incarceration.

But how does a person go about getting the best outcome? Unfortunately, statistics show that few people that encounter the criminal justice system know how to position themselves for the best possible result.

Section 2: Overview of Judicial Proceedings:

Relatively few Americans have more than a basic understanding of our nation’s criminal justice system. On the surface, people know that law enforcement officers arrest people, prosecutors bring charges, and some defendants who are convicted go to jail or prison. Yet the system is much more complicated than that, with many moving parts.

Targets should begin from the premise that the system has one function: to protect society. It has a series of procedures designed to enforce the laws of this country. The more we understand about the system, the better we can prepare to navigate the challenges.

All branches of law enforcement work together to prosecute crimes. Just as some offenders will make every effort to evade detection and apprehension by law enforcement, the different members of law enforcement will make every effort to solve a crime and win a conviction.

As citizens, we’re all charged with the responsibility of abiding by our nation’s laws. Legislators pass the bills, and heads of state sign the bills into law. It’s the criminal justice system that is responsible for enforcing the rules.

Few people understand that our country has 53 separate criminal justice systems, including one for each state, one for the District of Columbia, one for the military, and one for the federal government. Within the different systems, there are hundreds of jurisdictions, each with a series of trial courts that make findings of fact. Higher courts may review whether trial courts followed standard procedures.

This elaborately complex system has evolved over hundreds of years. For a person that enters the system, it can feel like authorities drop him into a byzantine labyrinth, with so many turns and dimensions that make it easy to lose direction.

To put this into perspective, think of the system as a zero-sum game.

We use the metaphor of a game for clarity, not to trivialize the conflict between the accused and the accuser. Defendants are the opponents of investigators and prosecutors. Both sides want to win. The defendants want to be diverted from prosecutions, acquitted, or receive the least restrictive sanction. Law enforcement officers want to convict. Prosecutors want to ensure that the defendants receive what they deem as an appropriate sanction.

In this “game” of criminal justice, the judge acts as a referee. Judges strive to ensure that both sides of the game adhere to the rules or due process. They must follow established procedures within the system. In some instances, juries will determine the outcome of this game. But in most cases, defendants will plead guilty before a judge. Then, the long game begins with post-conviction proceedings. They include a presentence investigation and a sentencing hearing. Classification processes follow. For some, the next step comprises appeals, imprisonment, supervised release, and all of the collateral consequences that stay with the “felon” class.

The sooner a target or a defendant starts preparing, the more influence that person can have on a better outcome.

As Mick Jagger sang, we don’t always get what we want. But if we try sometimes, we just might find, we get what we need. To understand what we need, we must work with a criminal defense attorney. And the more we know about what is to come, the better we prepare ourselves to help our lawyers get us the best outcome. For example, if we see what follows in prison, we may be in a better position to understand the impact of a plea agreement or a prison term. In all cases, knowledge can help us make more informed decisions and restore confidence.

Section 3: Understanding Sentence Mitigation

When is the right time to think about a sentence-mitigation plan?

Answering that question reminds me of an old saying about the best time to plant an oak tree. I heard a speaker ask that question to members of his audience. Predictably, audience members ventured a guess.

  • In the morning?
  • In the winter?
  • In the summer?

No one had a clue.

Pausing for dramatic effect, the speaker then answered. The best time to plant an oak tree was 20 years ago. The second-best time is today.

We could say the same thing about a sentence-mitigation plan. Too often, a defendant doesn’t do anything to prepare for the sentencing hearing.

It’s understandable. Many defendants don’t think of themselves as criminals. Regardless of what type of activity brought them to the attention of authorities, they believe that they’re different, immune from law enforcement. They may not know anyone that has been through the criminal justice system, and they cannot conceive of themselves going into the system.

  • How do you see yourself?

But authorities saw me differently. In their eyes, I violated securities laws. That made me a target for prosecution. And when federal authorities target a person for trial, their conviction rates exceed 85 percent. With those odds, it makes a lot of sense to begin thinking about a sentence-mitigation plan at the soonest possible time. Regardless of what type of charge a person faces, it’s essential to realize that sentencing proceedings will likely follow. Sentence-mitigation plans can help.

Start with an understanding of what the defense attorney will do. Attorneys will work with:

  • The evidence against the individual,
  • The procedural rules that determine what evidence the court will consider,
  • The substantive law that Congress has passed,
  • The case law that judges have decided,
  • The prosecutor’s ability to prove a case against the defendant.

To succeed, the defense attorney will exercise judgment and discretion, fighting valiantly to get the best possible outcome for the defendant. Both the prosecutor and the defense attorney will be analyzing the case and pressing forward to get the result they want. Rather than justice, the prosecutor will strive for a conviction. The defense attorney will parry the prosecutor’s efforts, always assessing the strength of arguments that he can use.

While the defense attorney may be a great analytical thinker, he may not have time to listen to the defendant’s life story. For that reason, every defendant should invest the time and energy to present that life story.

A life story can make all the difference in the world when it comes to sentencing. Indeed, our team has worked closely with many federal judges. We’ve spoken with dozens of federal judges about the importance of preparing for sentencing. Two of those federal judges sat for an interview with us. I asked those judges what steps a person could take to influence the judge’s decision. Each judge responded by saying that, when it comes to sentencing, they want to hear from defendants.

Our interviews with both judges are available for free through our YouTube channel under the following playlist:

Defense Attorney’s Position:

Some defense attorneys support a pro-active sentence-mitigation plan, while other defense attorneys resist such initiatives. Why?

As stated above, attorneys are great analytical thinkers. Since they know it’s the prosecutor’s burden to prove a case, they operate out of an abundance of caution. They do not want to introduce any evidence that a prosecutor could use against their client. And since most defendants start in denial, incapable of fully appreciating the system or the charges against them, some attorneys do not want their clients to say anything.

Attorneys may have invested considerable amounts of time in constructing an elaborate defense. They do not want their clients to make statements that prosecutors may twist, making it more difficult for the attorney to argue for leniency at sentencing. Defense attorneys may prefer to rely upon case law, facts, and what the prosecutor could prove.

We have a different perspective. Our team has interacted with more than 1,000 people that have gone through the criminal justice system. We’ve had personal interactions with state and federal judges. Based on our experience, defendants put themselves in a far better position when they engineer an effective sentence-mitigation plan. When a person creates and executes an effective sentence-mitigation strategy, that individual does immense service to his defense attorney.

In our view, an effective sentence-mitigation plan will strive to achieve several outcomes:

  • It will help the judge see and understand the defendant as an individual,
  • It will help the judge grasp influences that led the defendant to the current situation,
  • It will help the judge see aspects of the defendant’s life that could not be conveyed by the defense attorney’s eloquence alone,
  • It will help the judge see the defendant in his environment,
  • It will help the judge learn what other people in the community think about the defendant.

Engineering an effective sentence-mitigation plan does not excuse the misconduct or litigate the case. A sentence-mitigation plan does just the opposite. It is a strategy to show the judge why the defendant is worthy of mercy. It would not serve a defendant’s interest to minimize liability or to blame anyone. If referring to the criminal conduct at all, the sentence-mitigation plan should focus on some key points, including:

  1. Show an understanding and an appreciation for the victim’s pain, suffering, or loss.
  2. Show influences that led the defendant to become involved in the instant offense.
  3. Show what the defendant has learned from the experience.
  4. Show what steps the defendant has taken to reconcile with society, the victims, and his community to make things right.
  5. Articulate a coherent plan to show why the defendant will never break the law again.

What if I Go to Trial?

As stated in previous lessons, the vast majority of people charged in a criminal case start with a not-guilty plea. Their defense attorneys then assess the evidence and the risks of proceeding through trial, then negotiate the most favorable plea agreement possible. Still, a small percentage of defendants maintain their innocence and proceed through trial.

If a defendant proceeds through trial and is found guilty, that defendant may want to appeal. In that case, the defendant will want to create a sentence-mitigation plan that does not threaten the prospects for an appeal. Accordingly, he should refrain from discussing any aspects of the case. Instead, such a strategy should focus exclusively on helping the judge get to know him as a person.

There is always an opportunity to create a mitigation strategy. It is equivalent to building a sales presentation. And how do we accomplish that goal? We begin by thinking about our audience. A sentence-mitigation plan has an audience of one: the judge.

  • What steps can you take to differentiate yourself from every other defendant that comes before the judge?

First Person Approach:

Let your lawyer argue the law and deal with the evidence against you. When it comes to articulating the story of your life, use your own words, in a first-person voice. From our perspective, this is common sense.

Your lawyer is a professional advocate, skilled in the arts of persuasion. Even if the most notorious criminal retained your attorney, a professional code of ethics would require your attorney to provide the most zealous defense possible. After decades of practicing law, judges know that the defense attorney is going to argue for leniency at sentencing.

While deliberating over the appropriate sentence, the judge isn’t too concerned with arguments on case law. He has read the case law; he has his own opinion. On the other hand, he doesn’t know much about the defendant.

Before sentencing, defendants have an opportunity to influence the outcome. Again, a defendant does well when he starts from the premise that he’s about to make the biggest sale of his life. The only question is how well he has prepared, or how much time, energy, and resources he wants to build a persuasive case.

Three-Tiered Plan:

Our team believes that an effective sentence-mitigation plan should begin at the soonest possible time. No one can change the past, but any of us can start crafting a story that will show who we are as individuals and how we got here. We’re big believers in a three-tiered strategy that includes:

  • A personal sentencing narrative
  • A strategic character-reference letter campaign
  • A sentence-mitigation story of community service
    • Bonus: A sentencing video

Sentencing Narratives:

Based on what we’ve learned from judges, we believe that defendants serve themselves well when they write first-person, sentencing narratives. For defendants that have pled guilty, the sentencing narratives should adhere to the five-point list stated above, but that we’ll repeat here:

  1. Show an understanding and an appreciation for the victim’s pain, suffering, or loss.
  2. Show influences that led the defendant to become involved in the instant offense.
  3. Show what the defendant has learned from the experience.
  4. Show what steps the defendant has taken to reconcile with society, the victims, and his community to make things right.
  5. Articulate a coherent plan to show why the defendant will never break the law again.

If a jury or judge convicted the defendant after a trial, then it’s essential to consider the appellate strategy. Either way, a well-constructed narrative should focus on the judge’s perceptions, using the five-point above as a guideline. We’ve worked with many individuals that prepared effective sentence-mitigation strategies, even though they did not accept responsibility before being convicted after a trial.

Every case is different. There is no cookie-cutter approach. And there is no guarantee that a personal sentencing narrative will influence the judge. A defendant that engineers a well-crafted sentence-mitigation strategy will be in a better position than if he were to remain silent. No one should leave the judge without clarity about a person’s mindset, or the influences that led him into the predicament at hand.

A well-structured letter considers the audience. Judges get inundated with paperwork. When crafting the message, think about length. Our recommendation is to write a document of between 1,500 and 3,000 words. Some papers may go longer. Yet, in our experience, we’ve found this word count to be sufficient to write a coherent narrative. Keep in mind that we’re advocating for a multi-pronged approach that would include far more than the sentencing narrative.

Defendants should strive to write a highly personal story, adhering to the five-point plan above. The art of writing is re-writing. Take time to get it right. Ask others to read through the document. Other readers may offer guidance that can prove beneficial.

When it’s complete, share the letter with your defense attorney and consider his advice on steps to strengthen the document.

Character-Reference Letters:

The second component of an effective sentence-mitigation strategy includes a well-coordinated character-reference letter campaign.

See our Prison Professors YouTube playlist:

We reveal what we’ve learned from judges about character-reference letters. The judges with whom we’ve spoken tell us that rather than receiving character-reference letters from high powered professionals or celebrities, they want to read letters from people that knew the defendant best. They want to read stories that offer details showing something about the defendant’s character.

For example:

  • If the defendant volunteered as an athletic coach, perhaps someone from the team could write about memorable experiences of working with the coach.
  • If the defendant volunteered in the community, perhaps a program director could write about how the defendant helped someone without expectations of receiving anything in return.
  • If the defendant helped a sick neighbor with lawn care, or grocery shopping, that testimonial would show a great deal about the defendant’s character.

Ideally, the person that writes the character-reference letter should reveal that the defendant has been open and honest about criminal behavior. Judges want to know that the defendant has not been deceptive. If the writer feels that the defendant has expressed remorse, then the writer should show what he has seen.

Judges with whom we’ve spoken told us that ideally, a defendant would be selective. Rather than submitting an overwhelming number of letters, the judges with whom we’ve spoken said that it’s far better to send a few, well-crafted letters. Based on what we’ve heard, judges do not want to receive more than a dozen character reference letters—especially if they all present the same message.


Character-reference letters should never make excuses for the defendant. It would not serve the defendant’s interest if the character-reference letter:

  • Wrote that the defendant wasn’t at fault,
  • Stated that the government or jury got it wrong,
  • Opinionated that the defendant should not be going to prison,
  • Followed a template that many others wrote.

Judges want to hear about the defendant’s character. That is all. They do not want to listen to the writer’s opinion about the case, or the fairness of the judicial system. Nor do they want others to tell the judge what sentence would be appropriate. The judge wants to hear from those that know the defendant best. If they know about the defendant’s conviction, and they still express a willingness to support him, that says a great deal.

Sentence-Mitigation Story:

Finally, defendants that have the time and energy may want to build a story of mitigation. This strategy can include participation in a course or the creation of a class. It can consist of biography or some type of vehicle that shows the defendant’s commitment to making things right.

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