I always like to see echoes in enforcement actions, where something from this year is similar to the faces and factors of an earlier one. Some particular facts might be unique, but there are definite patterns.

So, I built an Gemini prompt to compare the latest action against all previous actions since 2012 (when the Enforcement Guidelines started showing up in the enforcement releases), find the best fit in each year’s actions, then rank those.

Yes, I will post the actual method I provided to Gemini – here are the results of this first attempt:

Based on the procedure provided, I have identified the most recent OFAC enforcement action as of December 5, 2025, which is the action against Gracetown, Inc. (issued Dec 4, 2025).

I have compared this “Anchor Case” against the enforcement actions from each year (2012–2025) to find the single best fit for that year. Below is the ranking of these yearly “best fits,” ordered from the strongest overall match to the weakest match.

The Anchor Case (Reference for Comparison)

• Entity: Gracetown, Inc.
• Date: December 4, 2025
• Determination: Egregious, Non-Voluntarily Self-Disclosed (Non-VSD).
• Duration: > 2 Years (April 2018 – May 2020).
• Key Behaviors: Willfulness/Recklessness; Ignoring explicit warnings (received direct OFAC notice regarding designated owner); Dealing in blocked property.

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Ranked Best Fits (2012–2025)

1. 2019: UniCredit Group Banks

• Date: April 15, 2019
• Fine: $611,000,000
• Match Analysis:
  • Matched Factors: Egregious (Factor 1); Non-VSD (Factor 8); Duration > 2 Years (Factor 5).
  • Behavioral Match (Factor 4): Strong. UniCredit operated accounts for blocked parties (IRISL) and ignored sanctions risks similar to Gracetown’s disregard of its owner’s designation. Both involved ignoring the blocked status of a known counterparty.
  • Mismatched Factors: UniCredit involved wire stripping (altering payment messages), which Gracetown did not explicitly do (Gracetown accepted payments via loan arrangements).

2. 2014: BNP Paribas SA

• Date: June 30, 2014
• Fine: $963,619,900
• Match Analysis:
  • Matched Factors: Egregious (Factor 1); Non-VSD (Factor 8); Duration > 2 Years (Factor 5).
  • Behavioral Match (Factor 4): Strong. BNP willfully ignored the status of sanctioned entities (Sudan, Iran, Cuba) and continued processing payments, paralleling Gracetown’s willful receipt of payments from a blocked owner.
  • Mismatched Factors: The scale of BNP’s systemic wire stripping was more complex than Gracetown’s property management violations.

3. 2023: Binance Holdings, Ltd.

• Date: November 21, 2023
• Fine: $968,618,825
• Match Analysis:
  • Matched Factors: Egregious (Factor 1); Non-VSD (Factor 8); Duration > 2 Years (Factor 5).
  • Behavioral Match (Factor 4): Strong. Binance management knew of the violations and willfully allowed them to continue, ignoring internal and external “warnings” about sanctions compliance, similar to Gracetown ignoring the OFAC notice.
  • Mismatched Factors: Binance’s lack of cooperation was noted as more severe (misleading regulators) compared to Gracetown’s standard posture.

4. 2015: Schlumberger Oilfield Holdings, Ltd.

• Date: August 7, 2015
• Fine: $232,706,600
• Match Analysis:
  • Matched Factors: Egregious (Factor 1); Non-VSD (Factor 8); Duration > 2 Years (Factor 5).
  • Behavioral Match (Factor 4): “Facilitation” of transactions for blocked parties. Schlumberger U.S. personnel facilitated business for Iran/Sudan, similar to Gracetown personnel managing property for a blocked oligarch.
  • Mismatched Factors: None significant; a very close procedural match.

5. 2017: ZTE Corporation

• Date: March 7, 2017
• Fine: $100,871,266
• Match Analysis:
  • Matched Factors: Egregious (Factor 1); Non-VSD (Factor 8); Duration > 2 Years (Factor 5).
  • Behavioral Match (Factor 4): ZTE received warnings and created an elaborate system to hide conduct. Gracetown also received a specific notice (the OFAC blocking notice) and continued dealing.
  • Mismatched Factors: ZTE involved a “Lack of Cooperation” (Factor 2) that was extreme (lying to federal investigators), whereas Gracetown’s cooperation was not flagged as deficient to that extent.

6. 2018: Société Générale S.A.

• Date: November 19, 2018
• Fine: $53,966,916
• Match Analysis:
  • Matched Factors: Egregious (Factor 1); Non-VSD (Factor 8); Duration > 2 Years (Factor 5).
  • Behavioral Match (Factor 4): Ignored warnings and processed payments for blocked parties.
  • Mismatched Factors: General banking sector behaviors (omitting data) vs. corporate property management.

7. 2012: ING Bank N.V.

• Date: June 12, 2012
• Fine: $619,000,000
• Match Analysis:
  • Matched Factors: Egregious (Factor 1); Non-VSD (Factor 8); Duration > 2 Years (Factor 5).
  • Behavioral Match (Factor 4): Management knowledge and willfulness.
  • Mismatched Factors: Factor 9 (Mitigating) — ING had substantial remediation credit which slightly alters the weighted comparison.

8. 2013: Weatherford International

• Date: November 26, 2013
• Fine: $91,000,000
• Match Analysis:
  • Matched Factors: Egregious (Factor 1); Non-VSD (Factor 8); Duration > 2 Years (Factor 5).
  • Behavioral Match (Factor 4): Export of goods/services to blocked countries; failure to heed compliance gaps.
  • Mismatched Factors: Less emphasis on “ignoring specific warnings from OFAC” compared to Gracetown.

9. 2016: National Oilwell Varco (NOV)

• Date: November 14, 2016
• Fine: $5,976,028
• Match Analysis:
  • Matched Factors: Egregious (Factor 1); Non-VSD (Factor 8); Duration > 2 Years (Factor 5).
  • Behavioral Match (Factor 4): Senior management approved dealings with Iran.
  • Mismatched Factors: The fine size and context (subsidiaries) are very similar to Gracetown, but the specific “ignoring of a blocking notice” was less central than in Gracetown.

10. 2022: Bittrex, Inc.

• Date: October 11, 2022
• Fine: $24,280,829
• Match Analysis:
  • Matched Factors: Egregious (Factor 1); Non-VSD (Factor 8); Duration > 2 Years (Factor 5).
  • Behavioral Match (Factor 4): Failure to screen/block (reckless disregard).
  • Mismatched Factors: Bittrex cooperated (Factor 2 was neutral/positive), whereas Gracetown was egregious partly due to the specific willfulness of ignoring the notice.

11. 2025: IPI Partners, LLC (Comparison within same year)

• Date: December 2, 2025
• Fine: $11,485,352
• Match Analysis:
  • Matched Factors: Non-VSD (Factor 8); Duration > 2 Years (Factor 5).
  • Mismatched Factors: Egregiousness (Factor 1) — IPI was determined to be Non-Egregious, making it a significantly worse match than the historical egregious cases.
  • Note: Gracetown (Dec 4) and IPI (Dec 2) are days apart, but the Egregiousness determination makes them dissimilar under your procedure.

12. 2021: Mashreqbank PSC

• Date: November 9, 2021
• Fine: $100,000,000 (Settlement)
• Match Analysis:
  • Matched Factors: Non-VSD (Factor 8); Duration > 2 Years (Factor 5).
  • Mismatched Factors: Egregiousness (Factor 1) — OFAC determined this case was Non-Egregious (despite the large fine, it was processed under non-egregious penalty caps due to cooperation). This fails the most important factor.

13. 2020: BitGo, Inc.

• Date: December 30, 2020
• Fine: $98,830
• Match Analysis:
  • Matched Factors: Non-VSD (Factor 8); Duration > 2 Years (Factor 5).
  • Mismatched Factors: Egregiousness (Factor 1) — Determined Non-Egregious. The violations were “reckless” but did not rise to the egregious penalty tier.

14. 2024: State Street Bank and Trust Company

• Date: July 26, 2024
• Fine: $7,452,501
• Match Analysis:
  • Matched Factors: Non-VSD (Factor 8).
  • Mismatched Factors: Egregiousness (Factor 1) — Determined Non-Egregious. Duration (Factor 5/6/7) — These violations were largely distinct processing errors rather than a multi-year sustained scheme like Gracetown. This is the weakest match as it lacks the “willful” behavioral characteristics.

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Summary of Factor Matches (Gracetown vs. Best Fits)

Factor	Description	Best Matches (2014, 2019, 2023)	Weakest Matches (2020, 2021, 2024)
1	Egregious?	MATCH (Yes)	MISMATCH (No – Non-Egregious)
2	Cooperation?	MATCH (Mixed/Satisfactory)	MATCH (Satisfactory)
3	Aggravating (Weighted)	MATCH (High score: Willful, Reckless, Management Knowledge)	MISMATCH (Lower score: System errors, technical failures)
4	Behaviors	MATCH (Ignored warnings, obfuscation)	MISMATCH (Screening tool errors, no active concealment)
5	Duration > 2 Yrs	MATCH	VARIES (Often match, but context differs)
8	Self-Reported?	MATCH (Non-VSD)	MATCH (Non-VSD)

So, how do you think the model did?