Ambiguity Trumps Advocacy: The Connecticut Supreme Court’s Remand Mandate When Separation Agreements Admit of Two Reasonable Meanings

1. Introduction

On 10 June 2025 the Connecticut Supreme Court delivered its opinion in Simpson v. Simpson (SC 20988), reversing in part the Appellate Court and establishing an important procedural-substantive principle for post-dissolution litigation. The Court held that when both parties offer plausible but conflicting “plain language” readings of a separation agreement, the agreement is necessarily ambiguous; therefore, the trial court must admit and weigh extrinsic evidence to ascertain the parties’ intent. The decision also clarifies the limited reach of judicial estoppel in family cases, refusing to penalise a party for changing litigation positions where no bad faith or prejudice is shown.

At the centre of the dispute was a single sentence in the parties’ 2013 separation agreement capping additional child support and alimony at the husband’s “gross earned income in excess of $700,000 per calendar year.” Whether that cap applied to the total of base draw and bonus (husband’s view, adopted by the Appellate Court) or only to the bonus component (wife’s view, adopted by the trial court) produced a difference of more than $300,000 in arrearages. The Supreme Court found the language genuinely susceptible of both constructions and ordered a remand for factual findings after consideration of “all available extrinsic evidence.”

2. Summary of the Judgment

Ambiguity Ruling. Sections 4.2 and 6.4 of the separation agreement, governing supplemental child support and alimony from bonuses/profit sharing, are ambiguous because they can reasonably be read either to exempt or to include income above $700,000.
Reversal and Remand. The Appellate Court erred in declaring the provisions “clear and unambiguous.” The case is remanded to the trial court for a new evidentiary hearing focused on intent and for recalculation of arrears and all interlocking financial orders (“the mosaic”).
Judicial Estoppel Rejected. A party’s shift from a “plain meaning” stance at trial to an “ambiguity” argument on appeal does not trigger judicial estoppel absent bad faith, inconsistent benefit, or prior court adoption of the first position.
Collateral Issues. The Supreme Court left intact the Appellate Court’s disposition of attorney’s fees and an educational-support order, affirming those limited portions.

3. Detailed Analysis

3.1 Precedents Cited and Their Influence

Nation-Bailey v. Bailey, 316 Conn. 182 (2015).
Confirmed the principles of contractual interpretation for separation agreements: ordinary meaning, whole-contract reading, and the ambiguity threshold. The Court leaned heavily on its articulation that ambiguous language creates a question of fact.
Parisi v. Parisi, 315 Conn. 370 (2015).
Provided the blueprint for remand when an agreement is ambiguous despite both parties’ claims of clarity; cited as authority that appellate courts cannot find facts in the first instance.
Dougan v. Dougan, 301 Conn. 361 (2011).
Key case on judicial estoppel. The Court borrowed Dougan’s three-factor test, distinguishing the present facts to refuse estoppel.
Contrasted Appellate Authority: Wells v. Wells, Grogan v. Penza, Halperin v. Halperin.
These cases involved unambiguous definitions of income that did not leave room for two plausible readings; the Court distinguished them to show why Simpson is different.

3.2 Court’s Legal Reasoning

Four-Corners Test Applied Globally, Not Selectively. The majority criticised the Appellate Court for isolating the “no support paid on gross income in excess of $700,000” sentence without reconciling it with neighbouring provisions that:
- Define “bonus/profit sharing” as gross payment less the normal draw;
- Express the parties’ post-sale income-sharing intention (50/50) in § 6.8;
- Prescribe different temporal ranges for base alimony (to 2022) and supplemental alimony (to 2024).
Plausibility on Both Sides Equals Ambiguity. Because both constructions had textual footing—one reading the cap globally, the other reading it as a bonus-only ceiling—the Court deemed the agreement ambiguous as a matter of law.
Question of Fact Requires Extrinsic Evidence. Once ambiguity is identified, intent becomes fact-driven. The trial court erroneously decided the issue without actually taking extrinsic evidence, notwithstanding its own declaration of ambiguity.
No Estoppel Without Bad Faith. Applying the New Hampshire v. Maine framework, the Court found:
- The wife’s positions (plain meaning vs. ambiguity) were not “clearly inconsistent” because her ultimate interpretation remained constant.
- The trial court never adopted her initial position.
- The shift conferred no unfair advantage and caused no prejudice.
Remand Scope Defined. The Supreme Court directed the trial court to:
- Receive testimony, documents, negotiations history, and practice evidence bearing on intent;
- Recalculate arrears and prospective obligations consistently with the factual findings;
- Re-craft the entire financial “mosaic.”

3.3 Impact on Connecticut Family Law

The Simpson decision will resonate beyond its facts in at least four ways:

Evidentiary Posture in Contempt/Modification Hearings. Trial counsel must be prepared to present extrinsic evidence—testimony about negotiations, drafts, industry compensation practices—whenever contractual language is susceptible to competing readings.
Drafting Caution. Family-law practitioners will pay closer attention to mathematical “order of operations” and definitions (e.g., “gross earned income”) to pre-empt future ambiguity litigation.
Clarified Limits of Judicial Estoppel in Family Cases. The Court’s rigorous application of the New Hampshire factors reassures litigants that tactical shifts are permissible absent bad faith or prejudice, encouraging appellate refinement of arguments.
Reaffirmation of the ‘Mosaic’ Doctrine. Because supplemental support provisions can interact with base support and other financial remedies, any error infects the whole mosaic and requires wholesale reconsideration on remand.

4. Complex Concepts Simplified

Ambiguity. A contract is ambiguous when intelligent people can read it in two different yet reasonable ways. Ambiguity is not created merely because parties disagree; the text must genuinely support both views.
Extrinsic Evidence. Any material outside the four corners of the contract—emails, drafts, negotiation notes, party testimony, industry norms—that illuminates what the parties meant.
Separation Agreement vs. Court Order. Once incorporated into the judgment, a separation agreement retains contractual interpretation rules even though it is also a court order.
Judicial Estoppel. A doctrine preventing a litigant from “playing fast and loose” with the courts by asserting contradictory positions in successive proceedings when the first position was accepted by the court and the change would cause unfair advantage.
Financial “Mosaic.” In family law, various financial orders (child support, alimony, division of property, attorney’s fees) form an integrated package. Altering one tile (e.g., the supplemental-support formula) may require reshaping the entire mosaic.

5. Conclusion

Simpson v. Simpson crystallises a pragmatic rule: where separation-agreement provisions admit of two coherent, textually supported readings, courts must treat the language as ambiguous, open the evidentiary gates, and determine intent as a factual matter. The decision guards against judicial over-confidence in textual clarity, reinforces whole-contract interpretation, and limits the punitive use of judicial estoppel. For practitioners, it underscores the importance of precision in drafting, vigilance in presenting extrinsic evidence, and strategic flexibility in argument. For the judiciary, it provides a roadmap for managing post-judgment family disputes in which contractual and equitable considerations intersect.