By Joseph De Gregorio, founder of Sentencing Advocacy Group and recurring Bloomberg Law contributor
Updated October 4, 2026
Prepare for federal sentencing with Sentencing Advocacy Group alongside you. Your hearing should not be the first time your preparation comes together. SAG helps you organize your history, document meaningful change and develop a clear, supported account of who you are today.
Work directly with Joseph De Gregorio on an individualized combination of sentencing strategies: judicial research, PSR interview preparation, accountability work, personal narrative development, character support and an organized evidence record. The aim is to strengthen the preparation behind your case and give each part of that work a clear purpose.
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How federal sentencing decisions are made
The guideline range is an important starting point, but it is not the entire sentencing inquiry. The Sentencing Commission’s 2025 application instructions describe two steps: calculate the guideline range and sentencing options, then consider the applicable factors under 18 U.S.C. § 3553(a). Counsel must determine which manual and legal requirements apply to your case.
Those statutory factors include the offense and your history, the purposes of punishment and deterrence, public protection, relevant treatment needs, available sentences, the guidelines and policy statements, unwarranted disparities and restitution. A government recommendation, an advisory guideline range and the sentence ultimately imposed are different numbers. Effective preparation keeps them separate.
Read the Sentencing Commission’s application instructions →
Read the official text of 18 U.S.C. § 3553 →
Where SAG strengthens your preparation
Probation gathers information about the offense, personal history and supporting records for the presentence report. That makes accurate, organized preparation valuable before the interview and during counsel’s review of the report. The U.S. Courts explains the presentence investigation here.
SAG helps you move from “I need to explain my situation” to a defined record of facts, actions and supporting sources. Joseph works alongside your defense counsel while taking responsibility for the preparation deliverables in your engagement.
Understand the record: establish deadlines, organize personal history and identify gaps. Receive a preparation roadmap and source checklist.
Document accountability: connect the conduct and harm to practical safeguards and verifiable progress. Receive an action plan, evidence index and chronology.
Develop your account: prepare your personal narrative and firsthand character support while preserving your own voice. Receive organized materials for counsel’s review.
Maintain continuity: connect sentencing preparation to surrender or release planning when that work is included in your scope.
Explore SAG’s connected frameworks and engagement deliverables →
What a client and an attorney say about the work
“Joseph's pre-sentence preparation was surgical precision.”
Daniel C. · Seattle, WA
Client testimonial excerpt · June 13, 2026
“Joe’s tenacity and genuine interest in helping clients get the best result is palpable. I'd gladly team up with Joe again, and wouldn't hesitate to recommend him to other counsel and their clients.”
Justin Danilewitz
Chambers-ranked white-collar defense attorney · Chair, White Collar and Government Enforcement Practice, Saul Ewing LLP
LinkedIn recommendation · October 13, 2025
Read the full recommendation →
Individual experiences illustrate the work; they do not establish a typical result. Explore client experiences and outcome details →
Discuss Your Sentencing Preparation With Joseph →
Five preparation questions drawn from judicial observations
Judges do not approach every case in the same way. Their published observations nevertheless offer useful questions for a preparation team: what is missing from the account, what has actually changed, who was harmed, what can be verified and what happens next? The short quotations below are historical sentencing observations. The practical explanations are SAG’s synthesis; the judges are not endorsing SAG or its frameworks.
1. Who is the person beyond the offense summary?
“I am sentencing the individual.”
Judge Jerome B. Simandle · 2017
A complete account holds two things together: the seriousness of the conduct and the individual circumstances of the person facing sentencing. An employment history, family responsibility or treatment record becomes more useful when dates, responsibilities and supporting sources are clear. Favorable facts should not erase uncomfortable ones.
Prepare: a personal-history chronology, the records supporting important events and a list of matters that require clarification. Ask character-letter writers for firsthand observations rather than a script. A specific example of conduct can help the reader understand a person more clearly than a string of adjectives.
This is the central question behind SAG’s Institutional Understanding Framework: who is this person today, and what evidence supports a different future?
2. What has changed—and can someone check it?
“Give me a plan. Tailor it to this defendant.”
Judge James C. Mahan · 2017
A useful plan responds to the circumstances that actually need attention. It identifies what will be done, who is responsible, what has already started and how progress will be recorded. A course unrelated to the conduct, an unconfirmed appointment or a general promise to make better choices should not be presented as proof that the underlying problem has been resolved.
Prepare: a dated action-and-evidence log. Distinguish enrollment from completion, attendance from a professional assessment and a proposed safeguard from one already operating. Record setbacks honestly. Where treatment is involved, the treating professional’s actual findings should govern the description.
The Compliance Rebuild Framework™ translates that preparation into an assessment, practical safeguards, an evidence index and a progress chronology.
3. How has the person understood and addressed the harm?
“What is best for the victim?”
Judge Lawrence J. O’Neill · 2017
An account of personal hardship is incomplete if it ignores the people affected by the offense. Preparation should distinguish understanding the harm from explaining the circumstances, and a completed restorative action from a future intention. Restitution records should identify amounts and dates accurately; neither charitable activity nor an expression of remorse should be described as erasing the harm.
Prepare: a clear record of completed payments, appropriate documented commitments and the changes intended to prevent further harm. Discuss disputed facts, proposed statements and any victim contact with defense counsel. Accountability does not require adopting an allegation that is inaccurate.
SAG’s ESG accountability framework examines the environment that enabled the conduct, social responsibilities and the oversight now in place.
4. What information does counsel need before the record takes shape?
“Get it to the probation officer early.”
Judge Justin L. Quackenbush · 2016
Preparation is a sequence, not a document delivered at the last moment. Records need to be collected, inconsistencies discussed and sensitive material reviewed. The practical starting point is a conversation with counsel about the schedule, who will supply information and what remains unresolved.
Prepare: a source list, a missing-record checklist and a factual chronology. When a draft report is available, flag concerns for counsel with the relevant paragraph and supporting document. Keep a question about factual accuracy separate from a disagreement about the legal calculation. Counsel determines the appropriate submission and objection process.
Use the PSR interview guide as a starting point, or review the scope of individual PSR preparation support. The attorney partnership page explains how the work is coordinated.
5. Is the plan for returning home workable?
“What are his plans upon release?”
Judge Amy J. St. Eve · 2016
A future plan becomes more credible when the practical arrangements can be explained: where the person proposes to live, which work opportunities are confirmed, how treatment would continue, how transportation would work and who has agreed to help. Label conditional offers and unresolved needs as such.
Prepare: a housing summary, employment status, treatment-continuity information and a support schedule with named responsibilities. Include alternatives if a key arrangement falls through. Family support is most useful when it describes what someone can actually provide.
This quotation concerns sentencing and future plans; it is not a statement about Bureau of Prisons eligibility or release dates. Early Release & Reentry Planning applies practical planning to the post-sentencing stage, where the governing requirements and decision-makers differ.
Turn observations into a preparation record
For each important claim, write down the supporting source, its date, who can verify it and the question still outstanding. Keep the client’s own account distinct from a third party’s observation and from counsel’s legal argument. Judicial research should help focus preparation; it does not predict the sentence or establish a formula that every judge follows.
See the frameworks, steps and deliverables → · Choose your stage for a Private Case Review →
What do federal judges consider in white-collar sentencing?
Federal judges consider the offense, the defendant’s history and characteristics, the advisory guidelines, available sentences, punishment, deterrence, public protection, treatment needs, sentencing disparities, and restitution. No single factor guarantees a particular sentence.
The framework comes from 18 U.S.C. § 3553(a). My practitioner approach focuses on making relevant information specific and verifiable, so counsel can connect it to that framework.
I explored that approach in my December 8, 2025 Bloomberg Law article, How to Get a Judge to Reduce Your Client’s White-Collar Sentence. This guide develops those preparation themes alongside my ABA, Federal Bar Association, and Law360 work.
How is a white-collar sentencing guideline range determined?
A loss figure alone does not establish the final range. Counsel must identify the applicable guideline, calculate the offense level and adjustments, determine criminal history, and account for statutory limits and the applicable manual.
Fraud and tax offenses should not be treated as interchangeable calculations. A proposed loss amount, a restitution figure, and the defendant’s personal gain also should not be assumed to mean the same thing. Ask counsel to identify the factual and legal basis for each number.
For tax-specific context, my March 11, 2026 Bloomberg Tax article, Tax Fraud Sentencing Has a Gap Defense Attorneys Are Missing, examines the distinction between sentencing calculations and restitution exposure. Counsel must assess the applicable law and plea terms; this citation does not establish that proposed language binds the court.
Cryptocurrency matters can also require careful reconstruction of roles and financial records. My May 14, 2026 Law360 analysis, Sentencing Tips For Defending Crypto Conspiracy Cases, addresses that preparation context. Our crypto role-timeline resource and blockchain-record checklist help organize material for counsel and qualified experts.
A useful working document separates the government’s position, probation’s calculation, the defense position, and the court’s eventual findings. The Sentencing Commission explains how offense level and criminal history intersect in its sentencing table and Chapter Five guidance.
What is the difference between a guideline objection and a variance?
A guideline objection challenges the calculation. A variance asks for a sentence outside the advisory range based on the statutory sentencing factors. They are different arguments, and a strong presentation may need to address both.
In A 3-Part Blueprint for Sentencing Variance Arguments, published by Law360 on July 14, 2026, I emphasize an accountability narrative, a reasoned deterrence analysis, and documented post-offense conduct. Reciting the statutory factors is different from showing how the evidence supports the requested sentence.
A request for a variance is not permission to ignore a statutory minimum or other legal restriction. Defense counsel should explain the sentencing options actually available in the case.
Why does the presentence report matter?
The PSR gives the court an organized account of the offense, sentencing calculations, and personal history. Preparing accurate information and reviewing the resulting report with counsel can help identify omissions and errors before sentencing.
My Federal Bar Association article, Judicial Sentencing Discretion After Booker: What the Pre-Sentence Report Actually Determines, examines how structured documentation can make individualized circumstances easier to evaluate.
The interview is not the only opportunity to address the record. Federal Rule of Criminal Procedure 32 provides for disclosure and objections. Confirm the actual deadlines with counsel. Submitting a personal narrative does not guarantee that probation will attach it in full.
Our PSR interview preparation guide includes the 25-question preparation framework from my nine-page Summer 2026 ABA Criminal Justice feature, The Mitigation Revolution: A Practical Guide to Engineering Drastic Federal Sentence Reductions.
What makes rehabilitation evidence useful?
Show what changed, when it changed, and what supports the account. A completion record, treatment history, or documented change in oversight gives the reader something to assess beyond a promise.
My December Bloomberg Law commentary discusses sustained treatment, educational progress, compliance work, and documented restitution. The practical task is to connect each activity to the person’s actual circumstances.
Education: distinguish enrollment from completed coursework.
Treatment: use appropriate records and the treating professional’s actual findings.
Compliance: explain the failure being addressed and the specific oversight now in place.
Community work: describe the work, dates, responsibilities, and people who can verify it.
There is no universal requirement to earn a degree, complete a particular course, or follow a fixed number of months of preparation. Build an accurate record within the circumstances and time available.
How should mental health information be presented?
Relevant clinical information should explain the individual’s history, functioning, treatment needs, and documented progress. A diagnosis alone does not establish a particular sentencing result.
In Keys to Effective Mental Health Mitigation in Sentencing, co-authored with Richard Levitt and published by Law360 on January 29, 2026, we discuss connecting qualified clinical evidence to individualized sentencing arguments.
Discuss relevance, authorizations, and sensitive records with counsel. Do not exaggerate symptoms or treat a generalized recidivism claim as an assessment of a particular person.
What role do restitution and victim harm play?
Restitution is an express sentencing consideration, but payment does not erase the offense or guarantee leniency. Accurate records should distinguish amounts paid, disputed losses, and realistic future payment proposals.
My April 20, 2026 Bloomberg Law article, Prepping for Fraud Payback Hearings Helps Clients Save Millions, addresses preparation for restitution proceedings, including financial evidence and loss methodology.
Work with counsel on the applicable restitution rules and any disputed amounts. A payment plan is different from a payment already made. Service or charitable work should not be presented as a substitute for a monetary obligation without a legal basis. Decisions involving family funds, retirement accounts, or asset sales need individual legal and financial advice.
How should character letters and accountability be handled?
Specific firsthand observations are more useful than a generic endorsement. Ask writers to explain how they know the person and what they have actually observed. Do not assign a numerical value to a famous person’s letter or dismiss evidence merely because it comes from family.
Accountability should be truthful and consistent with counsel’s advice. Do not adopt a suggested motive, concede an inaccurate allegation, or give up a legitimate objection to appear remorseful. The ABA framework emphasizes reflection supported by action; it is not a script requiring particular emotions.
What can a successful sentencing example tell you?
In a case I have described, the plea agreement listed a range of 168–210 months and the client received one year and one day. That sentence was more than 94% below the high end of the range stated in the plea agreement.
The comparison identifies its starting point. It does not establish that the court adopted that range, that mitigation alone caused the outcome, or that another client can expect the same result. Case examples are most useful when the underlying facts, recommendations, legal issues, and court findings are understood.
My December Bloomberg Law article and Federal Bar Association article discuss cases from my practice. They are authored practitioner commentary, not a promise of an outcome in your case.
What should you prepare before a sentencing consultation?
The charging document, plea agreement if applicable, and sentencing schedule.
The draft PSR and counsel’s list of disputed facts or calculations, if available.
A chronology of employment, family responsibilities, treatment, and other relevant circumstances.
Records supporting completed rehabilitation, payments, and proposed oversight.
A clear distinction between completed work and future plans.
Keep records organized and coordinate substantive submissions with defense counsel. Sentencing mitigation supports the legal representation; it does not replace it.
Further Bloomberg reading on compliance and enforcement
For related issues earlier in a matter, read my Bloomberg Tax article, Changes to IRS Disclosure Program Should Spark Compliance Checks, and my Bloomberg Law commentary, DOJ Enforcement Vacuum Opens a Strategy Window for Defendants. These address related topics rather than a formula for predicting a sentence.
Put the preparation work into practice
For preparation alongside defense counsel, review our services. If the presentence interview is approaching, see the defined scope of our federal PSR preparation service.
About Joseph De Gregorio
Joseph De Gregorio is the founder of Sentencing Advocacy Group, a recurring Bloomberg Law contributor, and has been retained in more than 500 federal cases. His authored work appears in Bloomberg Law, Bloomberg Tax, ABA Criminal Justice, Law360, and the Federal Bar Association blog.
Explore his publications and media appearances or learn more about Joseph. For planning after sentencing, see our First Step Act guide and Federal Prison Survival Guide.
Your next decision is how you prepare.
You do not need a completed packet before speaking with Joseph. Start with your current case stage, next deadline and the work already underway. The first conversation identifies where SAG can help; the written engagement defines your scope, deliverables and timing.
Before the PSR interview: organize your history and supporting information.
After the PSR interview: identify missing records and factual questions for counsel.
Approaching sentencing: prioritize the preparation still practical before your deadline.
Already sentenced: discuss surrender preparation and post-sentencing planning.
Request Your Private Case Review →
Prefer a brief first conversation? Request a 15-minute introductory consultation →
Call Joseph: 646-588-8182
Explore federal sentencing strategy and preparation → · Explore post-sentencing support →
General educational information. SAG is not a law firm and does not provide legal representation. Defense counsel advises on legal strategy, objections and submissions. Outcomes depend on individual circumstances and official decisions.
