Criminal tax preparation · A practical chapter

Tax Loss at Federal Sentencing: Building a Reviewable Record

Make the financial record traceable before sentencing. Organize tax periods, source documents and unresolved questions with Joseph De Gregorio, in coordination with defense counsel.

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

The useful question is how the number was built

A tax-loss figure should be traceable to periods, transactions, assumptions and source records. A single total does not explain which years it covers, how business and personal accounts were treated, or what remains disputed. This chapter helps individuals and their families organize a reviewable record for defense counsel and any tax professional counsel engages.

If your immediate concern is an agent contact or an active investigation, begin with the IRS criminal investigation guide. If sentencing is approaching, use this chapter alongside the federal tax sentencing overview and counsel’s case-specific instructions.

Tax loss is a guideline question, not a bank-balance question

Under §2T1.1, the base offense level ordinarily refers to the tax-loss table. The guideline defines loss for covered conduct and provides estimation rules. A later payment does not reduce tax loss under §2T1.1(c)(5). Unclaimed deductions or credits require timely, reliable support and satisfaction of the guideline’s conditions. Interest and penalties are generally excluded, with exceptions specified in the commentary. Counsel must determine the applicable guideline, manual and treatment of the facts.

Read the primary authority: United States Sentencing Commission, §2T1.1 and commentary. Do not infer a complete guideline range or likely sentence from a tax-loss figure alone.

Build a year-by-year source map

Start with an index, not a rewritten history. Keep original records intact. Give each source a stable label and record where it came from, when it was obtained and which issue it addresses. Use a separate working copy for annotations. Ask counsel how materials should be collected, stored and shared.

  • Tax period and taxpayer: Identify the year or quarter, individual or entity, and relevant return. Separate amended versions from original filings.
  • Amount and category: Identify what each figure represents, such as receipts, an expense, a transfer, a proposed adjustment or a payment. Do not label every deposit as income or every payment as a deduction.
  • Source: Cite the statement, return, ledger, invoice, transcript or correspondence supporting the entry, with a page or transaction reference.
  • Status: Mark whether an entry is documented, disputed, incomplete or awaiting professional review. A blank field should not silently mean zero.
  • Question for counsel: State the unresolved issue without presenting a legal conclusion as an established fact.

For the broader organization of business history, communications and personal records, see the criminal tax records map for counsel.

Separate the competing calculations

Maintain each version of a calculation with its date and author. A government worksheet, an accountant’s reconstruction and a client’s preliminary schedule may use different assumptions. Overwriting them into one spreadsheet can conceal the very disagreement counsel needs to understand.

A useful comparison identifies the line at issue, the amount in each version, the underlying documents and the reason given for the difference. For example, two schedules might treat the same transfer differently. The preparation task is to locate the originating and receiving records and flag the treatment for review. It is not to decide, without professional analysis, that the transfer must be excluded.

Where records are missing, keep a gap log. Record the missing period, the person or institution believed to hold the record, the request status and the limitations of any available substitute. Do not create a replacement invoice, backdate a record or present a reconstruction as a contemporaneous document.

Keep payments and restitution in their own record

Actual payments, promised payments and proposed future payments need different labels. Record the date, payer, recipient, tax period, confirmation and any evidence of crediting. A payment receipt and a statement showing how that payment was applied answer different questions.

For a detailed payment ledger and the distinction between guideline loss, restitution and a civil balance, continue to tax fraud restitution and financial-record preparation. Keeping these records separate allows counsel to evaluate each issue without confusing a sentencing calculation with a payment history.

Prepare for the presentence record

Financial information does not stand alone. A presentence record may also need an accurate employment chronology, dependents, health history, treatment records, current obligations and a practical plan. These materials should remain consistent with the financial source map and the account counsel has approved for use.

Begin early enough to identify contradictions while documents can still be located. If a business closed, distinguish the date operations ended from the date an entity was formally dissolved. If income changed, identify the period and supporting evidence. If a family member provides support, distinguish support already received from support merely offered.

See national PSR and presentence interview preparation for the broader preparation process. Counsel controls legal positions, objections and submissions.

Published analysis connected to the preparation task

Joseph De Gregorio’s Bloomberg Tax article, “Tax Fraud Sentencing Has a Gap Defense Attorneys Are Missing” (March 11, 2026), provides a related starting point for examining the personal record alongside financial issues. View the SAG Bloomberg Tax publication record.

His Bloomberg article “Prepping for Fraud Payback Hearings Helps Clients Save Millions” (April 20, 2026) addresses a separate preparation question: the restitution record. The publication title is not a prediction of savings in any case. See the SAG Bloomberg Law publication record.

What SAG prepares with you

Engagement begins with the case stage, counsel’s priorities and a defined written scope. Agreed work may include a source index, personal and business chronology, payment-history organization, a list of unresolved factual questions, and preparation for the presentence interview. Deliverables are organized for counsel’s review.

SAG does not calculate a binding tax liability, issue an accounting opinion, determine guideline objections or replace a criminal tax lawyer. Joseph De Gregorio is SAG’s Founder and President and a federal sentencing reduction and early release strategist. SAG is based in Freehold, New Jersey and serves clients nationwide, including travel when an engagement calls for it.

Common preparation questions

Should I build my own final tax-loss calculation?

Organize the records and identify questions. Counsel and the relevant tax professional should evaluate the methodology and legal treatment. Label any personal worksheet preliminary and identify its assumptions.

What if the documents disagree?

Preserve both versions. Create an exception entry showing the specific difference and its sources. Do not silently choose the version you prefer.

Can my family help?

Family members can often help locate authorized records and organize practical information. Counsel should set boundaries for access, communications and sharing. Do not assume coordination with SAG automatically makes every communication privileged.

Bring the record into focus

Start with the stage of the case, your next known deadline and whether defense counsel is involved. Use the initial inquiry to arrange a private conversation; do not send tax returns, account numbers or detailed allegations through the general form.

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Educational preparation guidance. Sources checked November 5, 2026. SAG is not a law firm and does not provide legal or tax advice. No sentence, payment outcome or release date is guaranteed.