Criminal tax preparation · A practical chapter
Business Owners Facing an IRS Criminal Investigation
Organize the company history, your individual responsibilities and the practical preparation needs. Work directly with Joseph De Gregorio alongside defense counsel.
By Joseph De Gregorio · Federal Sentencing Reduction and Early Release Strategist
Founder and President, Sentencing Advocacy Group
Published November 5, 2026
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Separate the company record from the individual record
An owner may be the public face of a business without performing every accounting, payroll or filing task. A preparation file should explain actual responsibilities over time, supported by records. It should also show the person’s own conduct and decisions accurately. A title alone does not establish who knew what, when an issue came to their attention or what they did next.
This chapter is for business owners and families organizing information alongside a criminal tax defense team. For the initial contact and investigation process, start with the IRS Criminal Investigation guide. SAG supports preparation; defense counsel directs legal responses and communications with investigators.
Establish the stage before building the account
The IRS describes investigations as evidence-gathering processes that may involve financial records and witness interviews. A recommendation for prosecution is distinct from a charge or conviction. See how the IRS describes the investigation process.
Record the actual communications received, their dates and any stated deadline. Preserve the documents for counsel. Do not substitute a family member’s interpretation of a letter for the letter itself, and do not assume an ordinary business contact reveals the investigation’s scope. Ask counsel to identify the current stage and the preparation priorities.
Build a responsibility timeline
A useful timeline distinguishes formal authority, day-to-day tasks and changes in personnel. For each period, identify the relevant entity, your position, the people handling the records and the documents showing the arrangement. Separate personal recollection from information confirmed by a contemporaneous source.
- Ownership and management: Record when interests or management duties changed, with agreements or corporate records where available.
- Accounting workflow: Identify who entered transactions, reviewed ledgers and supplied information to tax professionals.
- Filing and payment workflow: Identify who prepared, reviewed, approved or transmitted particular filings and payments. Preserve the evidence for each step.
- Access and notice: Record the systems and accounts used, and when correspondence or concerns reached each relevant person.
- Changes: Identify staff departures, provider changes, business closures and interruptions that affect the record.
This is an organizational map for counsel, not a conclusion about intent or liability. It should include inconvenient facts and unresolved questions as carefully as favorable information.
Keep entities, accounts and tax periods distinct
Many owner-operated businesses use several entities, locations or accounting systems. Organize the source material so a reviewer can see which entity and period each document concerns. Label intercompany or personal transfers for professional review rather than deciding their tax treatment yourself.
Retain original exports, statements and correspondence. A working spreadsheet should identify its preparer, date and source references. Do not overwrite earlier calculations or alter original documents to make them match a preferred account. Record missing material in a gap log and let counsel determine appropriate collection and preservation steps.
The criminal tax records map provides a broader organizational framework. If a loss figure has been identified, use the tax-loss preparation chapter to keep competing calculations traceable.
Describe business continuity as a practical plan
Owners often need to consider payroll administration, customer obligations, access to records and family income while a case is pending. List the operational questions without treating business necessity as permission to take a legally consequential step.
A practical plan identifies the proposed task, the person authorized to perform it, required professional review and evidence of completion. Keep proposed arrangements separate from those already operating. Counsel and the appropriate financial professionals should evaluate transfers, amended returns, disclosures and statements before action.
Document corrective work honestly
A new bookkeeper, written procedure or scheduled review is a starting point. The file should show whether the process was implemented, when it began and what records demonstrate its use. If a control failed or remains incomplete, say so. A policy document should not be presented as proof that every later filing or payment was correct.
Joseph De Gregorio’s July 27, 2026 Bloomberg analysis, “Changes to IRS Disclosure Program Should Spark Compliance Checks”, supplies a related compliance discussion. Review the two Bloomberg Tax publication entries and ask counsel about current rules. Publication does not determine eligibility for a disclosure practice or resolve a specific investigation.
Prepare the personal history without losing the business detail
Employment, health, dependents and treatment history may become important to later preparation. Keep these records organized separately from disputed financial issues. A truthful personal chronology should explain the owner’s work and responsibilities without turning unsupported business recollections into established facts.
If a plea or conviction brings sentencing into focus, move to the tax sentencing handbook and presentence interview preparation. The record can be developed in stages rather than rebuilt under a late deadline.
What a defined SAG engagement can deliver
Depending on the agreed assignment, SAG can organize a personal and business chronology, a source index, a responsibility timeline, a list of factual gaps and a preparation schedule. Joseph works directly with the client and coordinates the agreed handoff with defense counsel. SAG does not conduct a legal investigation, give tax advice or represent a person before the IRS.
Should I contact former staff to reconstruct events?
Ask counsel to set the process and boundaries for any outreach. Preserve existing records and identify potential information holders without directing anyone’s account or asking them to change records.
Can preparation start before charges?
Yes, a defined organizational assignment can begin while counsel handles the investigation. The work must fit the actual stage and counsel’s instructions; it is not a prediction that charges or sentencing will follow.
Discuss your stage and next deadline
SAG serves clients nationwide from Freehold, New Jersey, with travel arranged for cases. Start with your preparation need and counsel’s involvement. Do not send returns, account numbers or investigative documents through the initial inquiry.
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Published November 5, 2026. Educational information, not legal or tax advice. SAG is not a law firm. Outcomes depend on individual circumstances.