Date: Sep 18, 2026

Engellant v. Crowley Fleck (Mont. 2026): Validity of a Later Will as a “Negative Defense” Defeating Causation/Damages in Estate-Planning Malpractice

1. Introduction

Case: Engellant v. Crowley Fleck, PLLP, 2026 MT 218 (Mont. Sept. 15, 2026).
Parties: Daren Engellant (as Personal Representative of Gregory Engellant’s Estate) sued Crowley Fleck, PLLP and attorney Daniel N. McLean for legal malpractice in estate planning; Crowley Fleck brought third-party claims for contribution against family members (including Shana Diekhans and Kenneth Engellant).
Core dispute: Whether alleged malpractice in facilitating a lifetime stock gift caused the Estate damages when a later (2012) will allegedly would have sent the same stock to the same beneficiary at death anyway.

Gregory Engellant, under guardianship/conservatorship after a traumatic brain injury, met with McLean in 2012 to update his estate plan and expressed intent that his niece, Shana Diekhans, receive his ranch corporation stock. McLean prepared a will reflecting that intent and represented Greg in a September 2012 transfer of approximately $1.7 million in shares to Shana. After Greg’s death, Daren probated a 1978 holographic will, while litigation later erupted over whether a purported 2015 revocation was valid and whether the 2012 will should control.

Key issues on appeal included (i) whether evidence on the validity of the 2012 will was relevant to causation/damages in the malpractice case; (ii) whether a jury in a malpractice trial could decide whether the 2012 will was Greg’s last valid will despite the 1978 will’s probate posture; (iii) alleged instructional errors; (iv) exclusion of settlement evidence under M. R. Evid. 403; and (v) denial of post-judgment intervention as untimely.

2. Summary of the Opinion

The Montana Supreme Court affirmed the defense judgment for Crowley Fleck. The Court held that evidence bearing on whether Greg’s 2012 will was valid was relevant because it directly negated the Estate’s ability to prove causation and damages: if the 2012 will validly devised the stock to Shana, then the Estate would not have owned the stock even absent the lifetime gift. The Court further held that Crowley Fleck’s “2012 will” theory was a negative defense (contesting elements of plaintiff’s prima facie case), not an unpleaded affirmative defense.

The Court rejected arguments that the malpractice action improperly functioned as a collateral will contest or was barred by any preclusive effect of the probate proceedings, emphasizing that malpractice plaintiffs often must try a “suit within a suit.” The Court also found no reversible instructional error (including harmlessness where the jury never reached gift-capacity questions), upheld exclusion of confidential settlement evidence under M. R. Evid. 403, and affirmed denial of Kevin Engellant’s post-judgment motion to intervene as untimely.

Concurrence: Justice Bidegaray agreed with affirmance but emphasized an important conceptual distinction: testamentary capacity (supporting will validity) does not necessarily resolve the transaction-specific capacity and independent donative intent required for an inter vivos gift. The concurrence nonetheless found no basis to reverse due to waiver/acquiescence in the special verdict structure and failure to preserve a distinct damages theory.

3. Analysis

A. Precedents Cited (and How They Shaped the Decision)

Labair v. Carey, 2016 MT 272 (Labair II) & Labair v. Carey, 2012 MT 312 (Labair I)
These cases supplied the governing malpractice framework: duty, breach, causation (“but for”), and damages that must be fact-based and non-speculative. The Court used Labair II to justify the “suit within a suit” structure—i.e., litigating underlying issues (here, will validity) to test causation and damages in malpractice.
M. R. Evid. 401 and State v. Hudon, 2019 MT 31
M. R. Evid. 401’s broad definition of relevance supported admitting will-validity evidence; Hudon reinforced the district court’s broad discretion on relevance/admissibility.
Deschamps v. Treasure State Trailer Court, Ltd., 2011 MT 115; Weaver v. State, 2013 MT 247; Nitzel v. Wickman, 283 Mont. 304 (1997)
These authorities defined “affirmative defense” versus “negative defense” and the pleading consequences under M. R. Civ. P. 8(c). The Court relied on them to hold that contesting causation/damages is a negative defense governed by M. R. Civ. P. 8(b), not an unpleaded affirmative defense.
Baltrusch v. Baltrusch, 2006 MT 51; Ballas v. Missoula City Bd. of Adjustment, 2007 MT 299
Baltrusch supplied the collateral estoppel (issue preclusion) test. Ballas allowed the Court to treat Daren’s “issue jurisdiction” framing as substantively an estoppel argument. The Court held estoppel inapplicable because the probate court had not decided the identical issue on the merits, no final judgment existed on that issue, Crowley Fleck was not a party/privity, and it lacked a full and fair opportunity to litigate.
Probate jurisdiction: § 72-1-202, MCA and In re Estate of Cooney, 2019 MT 293
These confirmed that probate jurisdiction is limited and exclusive as to administering estates, but did not prevent a separate civil action from litigating will-validity facts for malpractice causation/damages purposes.
Waiver/Preservation: State v. Norman, 2010 MT 253; State v. Hicks, 2006 MT 71; Turk v. Turk, 2008 MT 45; Greytak v. RegO Co., 257 Mont. 147 (1993); Horn v. Bull River Country Store Props., 2012 MT 245
These cases enforced preservation requirements (raise issues below; specifically object to instructions/verdict forms). The Court leaned on Turk and related authority to hold Daren waived objections by affirmatively stating no objection to the special verdict form that stopped deliberations upon a “2012 will valid” finding.
Instruction review and harmless error: Estate of Mabee v. Wheatland Cnty., 2025 MT 252; Spotted Horse v. BNSF Ry. Co., 2015 MT 148; Camen v. Glacier Eye Clinic, P.C., 2023 MT 174; Tipp v. Skjelset, 1998 MT 263
These cases provided the standards for assessing jury instructions (full/fair statement of law; prejudice required) and harmless error. The Court deemed any alleged error in the “protected person gift capacity” instruction harmless because the jury never reached that issue under the verdict form.
Settlement evidence: Kruzich v. Old Republic Ins. Co., 2008 MT 205; Tripp v. Jeld-Wen, Inc., 2005 MT 121; M. R. Evid. 408; M. R. Evid. 403; State v. Peterson, 2024 MT 5
These authorities framed settlement policy and admissibility. Although M. R. Evid. 408 can allow settlement evidence to show bias, the Court upheld exclusion under M. R. Evid. 403 after an in camera/ex parte review of terms, finding limited incremental probative value and substantial concerns of prejudice/cumulativeness/confusion, consistent with Peterson’s deference to trial courts.
Intervention timeliness: M. R. Civ. P. 24; In re C.C.L.B., 2001 MT 66; Estate of Schwenke v. Becktold, 252 Mont. 127 (1992); Clark Fork Coal. v. Mont. Dep't of Envtl. Quality, 2007 MT 176
These cases supported denying intervention after final judgment where the proposed intervenor knew of the litigation well beforehand, confirming timeliness is a threshold and discretionary call.
Concurrence on gifts: § 72-5-421(5), MCA and Patterson v. Halterman, 161 Mont. 278 (1973)
The concurrence used these to highlight that being a protected person does not eliminate capacity per se, and that a valid inter vivos gift requires sufficient mental capacity and rational, independent donative intent—distinct from testamentary capacity.
Special verdict omission/waiver: M. R. Civ. P. 49(a)(3); Kleinsasser v. Superior Derrick Servs., Inc., 218 Mont. 371 (1985)
The concurrence invoked these waiver principles to explain why the unsubmitted factual issue (gift validity) could not support reversal.

B. Legal Reasoning (Step-by-Step)

Relevance as a causation/damages gatekeeper.
The Court treated will validity as a factual predicate to whether the Estate could show it would have owned the stock “but for” Crowley Fleck’s conduct. If the 2012 will validly devised all stock to Shana, the Estate’s claimed injury (loss of stock value) collapses: the Estate never would have received the stock in the first place.
“Negative defense,” not affirmative defense.
Crowley Fleck’s theory did not concede malpractice and then introduce new avoidance matter; it simply denied essential elements (causation/damages). Under the Court’s application of M. R. Civ. P. 8(b) and the cited cases, this is a negative defense not subject to waiver for failure to plead as an affirmative defense under Rule 8(c).
Separation from probate; acceptance of “suit within a suit.”
The Court emphasized that malpractice litigation routinely requires proving the outcome of an underlying dispute as part of causation/damages. The jury’s finding on will validity was limited to malpractice elements, not an adjudication binding the probate court’s administration of the estate under § 72-1-202, MCA.
No collateral estoppel from the probate proceeding.
Even if framed as “issue jurisdiction,” the estoppel elements were missing: no identical issue decided on the merits; no final resolution on the 2012-vs-1978 dispute; different parties/no privity; no full and fair opportunity for Crowley Fleck to litigate in probate.
Waiver through acquiescence in verdict form.
The Court gave independent weight to Daren’s express non-objection to a special verdict form that made “2012 will valid” dispositive and ended deliberations. Having accepted that structure, Daren could not later claim error that the jury was asked to decide will validity or that other issues were not reached.
Instruction challenges failed on prejudice/harmlessness.
A stipulated/probated-will fact was effectively before the jury through trial evidence, so omission caused no prejudice. Any asserted error in the “gift capacity” instruction was harmless because the jury never reached those questions after finding the 2012 will valid.
Settlement evidence properly excluded under Rule 403.
Even if bias is a permissible purpose under Rule 408, the district court did an ex parte review, found low marginal probative value given obvious existing bias (financial stake), and excluded for cumulativeness/prejudice/confusion while also respecting settlement policy.
Post-judgment intervention properly denied.
Timeliness is threshold. Because Kevin knew of the litigation years earlier and moved only after final judgment, denial was within discretion.

C. Impact (What This Opinion Changes or Clarifies)

Estate-planning malpractice defendants gain a clarified pathway to defeat causation/damages via testamentary documents. When the alleged malpractice concerns an inter vivos transfer, defendants may rely on evidence that a valid will would have produced the same economic endpoint, negating “but for” causation and the existence of damages to the estate.
Clarification of pleading doctrine in malpractice litigation. The Opinion reinforces that defenses aimed at negating elements like causation and damages are negative defenses under M. R. Civ. P. 8(b), reducing plaintiffs’ ability to strike such theories as “unpleaded affirmative defenses.”
Reinforced legitimacy of “suit within a suit” beyond classic underlying tort/contract scenarios. The Court approves using a malpractice jury to decide will-validity questions for the limited purpose of malpractice causation/damages, even while probate proceedings are ongoing, without converting the civil case into a probate adjudication.
Trial-structure and preservation lessons. The case underscores that verdict-form design can effectively determine what issues the jury will (and will not) decide, and that explicit acquiescence forecloses appellate relief.
Settlement confidentiality/bias evidence. The Opinion signals strong deference to district courts applying M. R. Evid. 403 to exclude settlement evidence even when offered for bias, particularly where bias is otherwise obvious and the settlement adds little.
Concurrence flags an unresolved doctrinal tension. While not the holding, the concurrence highlights that testamentary capacity does not automatically establish capacity/independent intent for an inter vivos gift—an issue likely to recur in cases involving protected persons, guardianships, and high-value lifetime transfers.

4. Complex Concepts Simplified

“Suit within a suit”: In legal malpractice, the plaintiff must often prove that, if the attorney had acted competently, the client (or estate) would have achieved a better result. That forces the malpractice case to recreate the “underlying” dispute (here, whether the 2012 will was valid) to show causation and damages.
Negative defense vs. affirmative defense: A negative defense argues the plaintiff failed to prove an essential element (like causation or damages). An affirmative defense accepts the plaintiff’s basic allegations but adds new facts that defeat liability (like statute of limitations, release, etc.). Only affirmative defenses must be “affirmatively stated” under M. R. Civ. P. 8(c).
Collateral estoppel (issue preclusion): If a court has already finally decided a specific issue between the same parties (or their privies), the issue generally can’t be relitigated. Here, the probate proceeding had not finally decided the identical 2012-versus-1978 will issue on the merits, and Crowley Fleck was not a party to probate—so no preclusion.
Probate jurisdiction vs. civil jurisdiction: Probate courts have exclusive authority to administer an estate (who gets what, how assets are distributed). But a civil malpractice jury can decide will-related facts for the limited purpose of determining whether malpractice caused damages—without binding probate administration.
Harmless error: Even if a jury instruction is imperfect, an appellate court won’t reverse unless the error likely affected the outcome. If the jury never reached the disputed issue (because the verdict form ended deliberations earlier), instruction error on that issue is typically harmless.
Testamentary capacity vs. capacity/intent to make an inter vivos gift: Testamentary capacity concerns whether a person can make a will. An inter vivos gift requires a transaction-specific ability and an independent, rational intent to give. A person might meet the will standard yet still lack the capacity or independent donative intent for a complex lifetime transfer (as the concurrence cautioned).

5. Conclusion

Engellant v. Crowley Fleck cements a practical and consequential rule for Montana malpractice litigation arising from estate planning: evidence that a later will validly would have transferred the disputed asset to the same beneficiary is relevant and may be dispositive on causation and damages, functioning as a negative defense rather than an affirmative defense. The Court also reaffirmed the “suit within a suit” model, rejected probate-based preclusion arguments on this record, and emphasized the decisive importance of preserving objections to special verdict forms and instructions. The concurrence, while agreeing with the result, usefully warns that will validity does not necessarily answer the separate question of whether a protected person had the capacity and independent intent to make a lifetime gift—an issue future litigants must preserve and present with a viable damages theory.