Criminal tax preparation · A practical guide
Large Tax Loss at Federal Sentencing
A large dollar total should be traceable to its underlying records. Organize the calculation questions and the person’s circumstances as separate, connected preparation assignments.
By Joseph De Gregorio · Federal Sentencing Reduction and Early Release Strategist
Founder and President, Sentencing Advocacy Group
Published November 5, 2026
Request a Private Case Review · (646) 588-8182
Make the total understandable
In a multi-year or multi-entity matter, a headline tax-loss figure can conceal several different assumptions. Identify the periods, taxpayers, source documents, method and preparer associated with each component. Keep competing calculations visible rather than replacing one without explanation.
Counsel determines the applicable guideline, relevant conduct and legal arguments. A preparation index should show where a number came from and which questions remain unresolved. It should not present a client-created spreadsheet as an expert conclusion.
Separate tax loss, unpaid balances and restitution
Sentencing tax loss is not simply the current account balance. Restitution, civil tax assessments, interest, penalties and payments can involve different rules and periods. Use a separate schedule for each purpose, with cross-references where the same transaction appears.
The Sentencing Commission publishes the governing guideline materials. Counsel must determine the edition and provisions applicable to the case. SAG does not calculate a guaranteed sentencing range from a dollar amount or assume that a payment automatically changes guideline loss.
Control versions and supporting evidence
For each calculation, keep the original file, date, author and stated assumptions. Record whether a revision corrects a transcription problem, adds a document or changes a method. A reviewer should be able to understand the change without comparing unexplained totals.
Large files benefit from a source index: bank statements, returns, payroll records, business ledgers, expert reports and payment confirmations. Use reliable identifiers and identify missing periods. Do not fill gaps with invented figures or unlabeled estimates.
Document payments and practical capacity accurately
A payment ledger can identify the date, amount, source, recipient, intended allocation and confirmation received. Separate completed payments from proposed sales, borrowing or future earnings. Counsel and financial advisers should evaluate the legal and practical implications of any plan.
A credible personal financial record also identifies obligations, ownership interests, available documentation and restrictions. Asset value is not the same as available cash. SAG helps organize the supporting record without giving asset-transfer advice or suggesting ways to conceal property.
Prepare the person as carefully as the numbers
Substantial financial allegations do not make personal history irrelevant. Develop a documented account of actual responsibilities, employment, family obligations, health-related needs through appropriate channels and completed changes. Avoid treating professional success or charitable claims as substitutes for accountability.
Joseph can coordinate an indexed personal record, chronology and preparation schedule with counsel. The goal is a file that can be evaluated and corrected. No publication, payment or preparation package guarantees a variance or a particular sentence.
Sources and related preparation
United States Sentencing Commission: 2026 Guidelines Manual. Source checked November 5, 2026. Counsel must evaluate the rules and facts applicable to your case.
Does a multi-million-dollar figure determine the sentence by itself?
No. Counsel must evaluate the applicable law, guideline calculation and case-specific factors. SAG does not predict a sentence from the amount alone.
A defined engagement with Joseph De Gregorio
Retain qualified federal defense counsel first for an investigation or criminal charge. Agree on the scope, records, authorized recipients and review dates before SAG’s work begins. Counsel retains legal advice, strategy and submissions. SAG can deliver an indexed personal record, a chronology, a factual gap list and an agreed preparation schedule. An engagement does not automatically make every communication privileged; counsel determines the appropriate arrangements.
SAG serves clients nationwide from Freehold, New Jersey, with travel arranged for cases. Tell Joseph your current stage and next deadline. Do not send case documents or sensitive allegations through the initial website form.
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SAG is not a law firm and does not provide legal or tax advice. Courts and agencies determine outcomes. No sentence, charging decision or release date is guaranteed.