If you’ve been following along sequentially, you’ve worked through seven lessons of our Straight-A Guide program. These were the same methodical steps that carried me through 26 years in prison. More importantly, these steps helped me to get out of prison with my dignity intact, and with opportunities to thrive.

Every person on our team at Prison Professors has had a great experience after going through a challenge from the criminal system. And we know that any person that served time alongside of us could have had a similar result. 

People can advance prospects for a better outcome if they stay aware of opportunities, and they sow seeds that will make others aware of the reasons why they’re worthy of consideration for leniency—or for higher levels of liberty, at the soonest possible time. 

For that reason, we offer this eighth lesson in our Straight-A Guide: Awareness.

At this stage, participants should have a clear strategy of how to influence stakeholders in the system. An effective mitigation package begins with open-ended questions that will accomplish two objectives: 

1. It will make the defendant more aware of opportunities to make him appear more humane, and less criminogenic.

2. It will make the judge aware of personal investments the defendant has made to reconcile with victims and with society, differentiating him or her from other people that come for sentencing.

At Prison Professors, we’ve published more than 1 million words of instruction, and more than 1,000 videos to help people understand the steps to take. In the end, each defendant must do the work—or bring someone on the team who can do the work. 

Those who’ve gone through each of the lessons in this course will have had opportunities to respond to hundreds of questions. In this module, we’re going to tie those questions together. 

Remember that good sentencing advocacy requires a full exposition of all factors in the defendant’s life. The more a defendant can explain influences leading to the point at which the crime took place, the better. It’s especially helpful to show what the defendant learned from the experience. Build themes in the defendant’s life that are highly personal. To a stakeholders, these themes may make the defendant appear more humane, and less like an undesirable criminal. 

Rather than concluding with 10 questions, through this module on awareness, we’re going to offer 20 questions. Each question will offer brief commentary for participants to consider. If the defendant’s mitigation package does not address each issue, then use this program to adjust. 

1. In what ways does your package discuss your role in the offense?

• Remember that your sentencing judge will be accustomed to people who prevaricate or minimize their involvement. Judges will look at such statements as being unworthy of mercy. Any defendant who fails to accept full responsibility may be better off to refrain from submitting anything. From a judge’s perspective, pleas for mercy require a full acceptance of responsibility.

2. What does your mitigation package reveal about accomplices?

• It’s crucial to remember that you’re going through this exercise with one objective: You’re trying to influence the judge. The judge has certain beliefs about law-abiding, contributing citizens. Someone who aspires to live as a law-abiding, contributing citizen, would always cooperate fully with law enforcement. That means they would reveal everything they know about the crime, and everyone who was involved. With a mitigation package, then, a defendant must draw a line in the sand. The package must offer definitive proof that the defendant is breaking all ties with crime, and forging strong ties with law-abiding, contributing citizens.

3. What role did drugs or alcohol play in the offense?

• This is a tricky factor. On the one hand, defendants sometimes fret that if they reveal an accurate history of substance abuse, federal judges and others will consider them a higher risk of reoffending. On the other hand, a well-framed mitigation package may show that abuse of drugs and alcohol led to the criminal behavior. Resolving substance abuse problems, therefore, would make the defendant less vulnerable to influences that lead to criminal behavior. It’s tricky because we do not want to excuse or justify the criminal conduct. Defendants must be careful to assess every sentence in the package to make sure that there isn’t any shifting of blame.

4. Does the mitigation package suggest that a desire to provide necessities for his family—for himself—motivated or influenced the defendant to engage in crime?

• This approach suggests that the defendant is basing his plea for mercy on hardship. But be careful. Prosecutors will cite other people with needs who did not break the law. Anticipate that the prosecutor will counter any request for mercy by contrasting the defendant’s criminal behavior with countless other people who chose to live in compliance with the law. Rather than committing crimes, those people sought assistance from charities, agencies, churches, and schools. A defendant must anticipate every argument the prosecutor will make, and build a case that will undermine prosecutorial efforts to place the defendant in the worst possible light. Defendants can reframe this argument in a manner that suggests he has poor judgment, or an inability to cope. Perhaps he needs mental health treatment, or intervention. Always take full responsibility.

5. Does the defendant claim that he believed the conduct was legal?

• Consider this the “Scott Tucker” approach. We wrote about Scott Tucker in a previous module. Scott spent millions of dollars on legal opinions to justify the massive payday-loan business he created. Scott exercised his right to go to trial. A jury convicted him within minutes. Following his conviction, he continued to make a case that his conduct was completely legal. The judge excoriated Scott, citing his lack of remorse. Netflix featured Scott on episode 2 of the series “Dirty Money,” which portrayed Scott harshly. Neither judges nor juries are sympathetic to pleas for mercy when a defendant claims ignorance of the law.

6. Does the mitigation package make any claim that the victims provoked the criminal episode?

• Nothing will bring more danger to a mitigation effort than to claim that a victim is responsible for the criminal wrongdoing. Be certain that the mitigation package emphasizes empathy with the victim, and a willingness to reconcile.

7. Does the mitigation package claim that no one got hurt from the crime, or that only consenting adults were involved?

• Such a statement is toxic to the criminal justice system. By using that strategy, claiming that since only consenting adults were involved in my crime, I exposed myself to the wrath of the criminal justice system. My judge slammed with a 45-year term because I failed to accept full responsibility. I also failed to acknowledge the magnitude of my errors. Remember how judges think. As citizens, we have a duty and a responsibility to act in accordance with the law. We cannot break laws, claim that the laws were not relevant., then ask for mercy.

8. Does the mitigation package claim that the degree of property loss isn’t accurate?

• Leave such statements to the defense attorney. Defendants cannot make such claims without appearing unrepentant. If a defendant acted with full intent to violate laws, prosecutors will ask the system to punish that person. Regardless of whether the loss occurred, anticipate that prosecutors will urge the court to sentence the defendant for the harm to which he exposed victims because of his nefarious, or selfish intent. Make sure the sentence-mitigation package leans toward remorse, and avoids excuses or justifications. Remember the case of “Pharma Bro” Martin Shkreli. His claim that he should not be sentenced harshly because investors did not lose money; on the contrary, they made money. But U.S. District Court Judge Kyo Matsumoto rejected those arguments. In a written decision, the judge found Shkreli should be penalized for losses of $10.5 million because he made risky transactions without permission from his investors.

9. Does the defendant claim that the judge should be merciful because of the unlikelihood that the defendant will engage in the same type of criminal behavior?

• This factor may address a low likelihood of recidivism. Yet it doesn’t address society’s need to punish. A sentence mitigation package should not endeavor to tell the judge how to sentence. Rather, defendants should write the package in such a way that shows what the defendant has learned from the episode and all of the events that unfolded. He should show the influences that led to his behavior, without offering excuses. He should humanize his behavior, leading the judge to an organic conclusion that mercy may be appropriate in this case.

10. Does the mitigation package put too much emphasis on the defendant’s good character, habits, education, or social status, suggesting that why he is unlikely to commit another crime?

• Although these factors may appear favorable on the surface, be cautious of coming across as arrogant. A defendant does not do himself any favors if he leaves the judge with the impression that he does not appreciate the severity of the crime, or thinks that he is above the law. Also, anticipate that a higher social standing or education, theoretically, could make a defendant more culpable because of his privilege. Make sure the mitigation package does not diminish a defendant’s appreciation for the severity of the offense, or the victims that suffered because of the crime.

11. Does the mitigation package sufficiently address the defendant’s employment history?

• Never underestimate the value of living as a tax-paying citizen. If a defendant has a long history of reliable employment, build a case that documents such contributions to society. Strive to include letters of recommendation that will show the efforts a person has lived as an honorable member of society. At the same time, add commentary to show humility and express shame for behaviors that led to criminal misconduct.

12. In what ways does the mitigation package reveal the defendant’s general emotional condition and mental health?

• In some cases, a defendant can self-diagnose, showing how hard he has worked to introspect. A good mitigation package will show the impetus for change and self-reflection, along with evidence of the work that the defendant has invested to overcome character flaws. Yet in some cases, it may make sense to hire a professional who can conduct an expert assessment. A defendant must exercise good judgment here, determining the best way to build a record that would show he fully appreciates the magnitude of the crime, and that he is doing everything within his power to make things right.

13. How does the mitigation package address the defendant’s educational background, his home life, or his sobriety?

• If it’s possible, include documentation to show courses completed and credentials earned. Defendants can strengthen their petitions for mercy when they build arguments showing that they have a history of work, of living in compliance with society’s expectations. If the defendant hasn’t earned credentials, then the defendant should address this fact, describing how a lack of education influenced his thinking and his behavior. Build a narrative that will help the judge grasp a better understanding of the person he is about to sentence.

14. What does the package say about the candidate’s likelihood of returning to the community as a contributing citizen?

• The essence of the mitigation package should show that the defendant identifies with the pain that he or she has caused to victims, and that he or she is working to make things right. Yet a package should also show a defendant’s commitment to live as a law-abiding, contributing citizen. That doesn’t mean the defendant should speak about saving the world by working with at-risk kids, or volunteer in rehab centers. Judges want to know that the defendant has taken steps to further the possibilities of being able to overcome the conviction and earn a living as a contributing citizen.

15. In what ways does the mitigation package address why the defendant failed to live in accordance with the law, and what he’s done about it?

• Obviously, the judge is familiar with statements from defendants who say “I should have known better.” When judges are about to sentence people to prison, they expect defendants to say anything. It’s much more important for the mitigation package to address what the defendant has learned from the offense. If the defendant can pinpoint the influences in his life that led him astray, the judge may be more inclined to believe that the crime was an aberration—or if not an aberration, the defendant has changed in ways to lead a values-based, goal-oriented life. We encourage defendants to indicate that they voluntarily enrolled in the Straight-A Guide Program and learned a great deal by advancing through the extensive self-study course.

16. How does the mitigation package show that the defendant has a strong possibility for successful treatment?

• If the defendant worked through the Straight-A Guide program, the defendant will offer the judge tangible evidence of his capacity to work. No two mitigation packages would be the same, because each defendant’s responses would be highly personal and they would be replete with documentation. Judges respect that type of self-study, that type of introspection. Judges know the length of time necessary to reflect and write. A solid mitigation package provides incontrovertible evidence that the judge can hold, see, read, and believe. The package would represent more than words on a page. The package would show a blueprint for life.

17. Can the defendant offer evidence from experts that show solid prospects for rehabilitation or lawful employment?

• If the defendant works through the Straight-A Guide program, and uses the team at Resilient Courses, the team can provide a certificate and a letter attesting to the defendant’s work ethic. Since members of the Resilient Courses team represent exactly what every tax payer wants our prison system to produce, judges cite our co-founders as experts. You can see testimonials from judges on our YouTube page. Our team can even film or record an interview that you can provide to the judge, showing how and why we validate defendants as excellent candidates for ongoing success.

18. What reason does the judge have to consider an alternative sanction, such as probation or community service?

• A solid mitigation package will include research about possible alternative sanctions that include probation and community service. Although some statutes prohibit noncustodial sentences, judges have far more discretion since the U.S. Supreme Court issued its opinion in the Booker case, back in 2005. Even if noncustodial sentence isn’t feasible, the mitigation package should offer suggestions that could motivate the judge toward mercy. Cases are all different because people are all different. Yet when framing the mitigation argument, a defendant must begin from the perspective of the judicial system, meaning there should not be any suggestion that the judge may construe as “minimizing the severity of the offense.” Offer reasons that will lead the judge to construe that a merciful sentence is appropriate, without telling the judge what to do or what is just.

19. If the defendant confessed and cooperated, what does the mitigation package suggest prompted such a move?

• The mitigation package should reveal precisely what triggered the defendant to begin cooperating with the government. In most cases, defendants plead guilty and cooperate for self-serving reasons. Think of the prosecutor’s version of events, and the judge’s interpretation. Those stakeholders may believe that the defendant isn’t truly remorseful. They believe that the defendant pleaded guilty and cooperated because he feared of a lengthier sentence if convicted at trial. Such a position may result in a sentence that is consistent with the plea agreement. Yet defendants who want to persuade the judge to impose or more lenient sentence will invest time, energy, and resources to build a compelling case of remorse. Provide a detailed, elaborate description of events or influences that resulted in change of thinking. In Earning Freedom, for example, I wrote about reading Socrates in my jail cell. Exposure to philosophy gave me an entirely new perspective on life, and the new perspective would guide my every thought through the 45-year prison term that I served. Defendants who incorporate such background into the mitigation package may position themselves for a more lenient sentence. They must help the judge see and appreciate the magnitude of change in thinking patterns.

20. In what ways does the defendant’s behavior after the time of arrest show that he has learned from this offense?

• We cannot underestimate the value of this point. Let’s contrast Jeremy with John, two clients our team worked with in the past. Both men pleaded guilty to financial crimes. Both men had advanced university degrees prior to their criminal convictions, and both men cooperated with authorities after their conviction. Both men passed about 12 months in society from the time they were caught until the time they were sentenced. During those 12 months, Jeremy supported himself by working long hours as an Uber driver. He lived modestly and humbly, doing everything possible to scrape by. At sentencing, the judge commented on Jeremy’s humility and willingness to do whatever was necessary to live in compliance with the law, even though the job was less prestigious than the role he previously held as a physician. John took a different path. Prior to his arrest, John worked as an investment advisor. After his conviction, he lost his license to trade securities. Instead, he launched an online business to teach others how to make money in the stock market. Yet rather than using his real name, John used an alias so that others would not know about his conviction for fraud. The judge cited John’s behavior as evidence that, despite his guilty plea and cooperation, he was failing to live honestly, as a truthful man. Although John wasn’t breaking the law, the judge had an unfavorable view of John’s activities and sentenced him to six months longer than the prosecutor requested. For that reason, we urge defendants to think carefully about how their mitigation package will reflect the defendant’s decisions after arrest.

21. What does the mitigation package reveal about restitution?

• Remember that actions speak louder than words. If financial loss is a factor in the case, consider making an effort prior to sentencing to pay toward that loss. We’ve seen defendants move the court by making modest payments toward restitution. Any effort that will differentiate a defendant in a positive way advances prospects for mercy. We encourage defendants to make deposits with the defense attorney that will go toward restitution, and to document those payments in the mitigation package.