Background
Kyle Whitehead and Gregory Huenergardt were equal 50% members of Cornerstone RX, LLC, a pharmaceutical buying group. Attorney Craig Riffel of the Riffel, Riffel & Benham firm served as personal counsel to both men over the years, represented them jointly in forming Cornerstone, acted as ongoing corporate counsel for the LLC, and was working with both members before Whitehead’s death to establish a new group purchasing entity to succeed Cornerstone’s existing business arrangements.
Kyle Whitehead died in March 2023. His wife Lora, as personal representative of his estate, filed suit in Ellis County District Court against Huenergardt for breach of fiduciary duty and breach of the operating agreement, alleging that Huenergardt used the new entity — allegedly Red Dirt Pharmacy Consultants, LLC — to cut the estate out of Cornerstone’s business and deprive it of the value of Whitehead’s 50% interest. The estate also sought an accounting from Cornerstone.
Despite this history, Riffel entered an appearance on behalf of Cornerstone in the litigation, and another Riffel Firm attorney filed a motion to dismiss on behalf of Huenergardt. The estate moved to disqualify Riffel and the entire firm based on conflict of interest. Riffel withdrew personally, but the firm continued to represent both defendants. After an evidentiary hearing, the trial court disqualified the Riffel Firm on February 14, 2025, finding all three elements of a Rule 1.9 conflict: a prior attorney-client relationship, substantially related subject matter, and materially adverse interests. Huenergardt and Cornerstone appealed.
The Court’s Holding
The Oklahoma Court of Civil Appeals affirmed the disqualification order in full. The court held that the Riffel Firm faced a straightforward conflict of interest under Oklahoma Rule of Professional Conduct 1.9(a) because Riffel had formerly represented Whitehead — and, by extension, the estate standing in Whitehead’s shoes — in the very transactions now at issue: the formation of Cornerstone, the drafting of its operating agreement, and the planning for the new successor entity. Representing Huenergardt and Cornerstone against the estate in claims arising from those same transactions amounted to switching sides in a substantially related matter.
The court rejected defendants’ argument that disqualification required an explicit finding that Riffel possessed confidential information. Distinguishing the conflict here as one grounded in the duty of loyalty under Rule 1.9(a) — not merely improper use of confidential information under Rule 1.9(c) — the court held that a lawyer who was directly involved in a specific transaction may not subsequently represent adverse clients in that same or a substantially related matter, regardless of whether confidential information is separately identified. Because Riffel personally would be disqualified, Rule 1.10(a) imputed that disqualification to the entire firm.
The court also rejected the argument that the estate lacked standing to raise the conflict because Lora was not herself a Cornerstone member. The court reasoned that Riffel had represented Whitehead during his lifetime in the matters at issue; the estate was asserting Whitehead’s interests in those same matters; and allowing the firm to proceed would undermine the purpose of Rules 1.7 and 1.9 to protect former clients from divided loyalties and potential use of their material information against them.
Key Takeaways
- An attorney who represented both members of a two-person LLC in forming the company, drafting its operating agreement, and planning successor transactions is disqualified — along with his entire firm — from representing one member against the other’s estate when those transactions become the subject of litigation.
- Disqualification under Rule 1.9(a) turns on the duty of loyalty and the substantial relationship between prior and current matters; courts need not separately find that the attorney possesses specific confidential information when the conflict is that the lawyer is effectively “changing sides” in the same transaction.
- Imputation under Rule 1.10(a) extends a conflicted lawyer’s disqualification to the whole firm unless the conflict is based solely on the individual lawyer’s personal interest — a narrow exception that did not apply here.
- A deceased client’s estate may invoke Rule 1.9 to disqualify opposing counsel based on that counsel’s prior representation of the decedent, even before the estate’s membership interest in the LLC has been formally resolved in probate.
Why It Matters
This decision serves as a pointed reminder for attorneys who act as general counsel or “family lawyer” for closely held businesses and their principals: representing the entity and both co-owners over time creates a conflict that forecloses later representation of one side against the other when a dispute erupts. The court’s analysis makes clear that this disqualification flows from the duty of loyalty embedded in Rule 1.9(a), not merely from the confidential-information provisions of Rule 1.9(c) — meaning attorneys cannot avoid disqualification simply by arguing they hold no secrets.
The opinion also has practical significance for estate and probate practitioners. By confirming that a decedent’s estate can stand in the former client’s shoes to assert a Rule 1.9 conflict, the court protects the integrity of post-death litigation involving closely held business interests, preventing a surviving co-owner from gaining a strategic litigation advantage by retaining shared corporate counsel after a dispute arises.