Clarification of Damages Certainty Requirement and Discretionary Attorney’s Fees in Breach of Contract Cases

Introduction

In Rick Holloway and John Hoskin v. Hidden Creek Outfitters, LLC and Park County Title Company, LLC (2025 WY 59), the Wyoming Supreme Court addressed the plaintiffs’ (Holloway & Hoskin) appeal from the district court’s finding that they failed to prove contract-related damages with sufficient certainty and denied their request for attorney’s fees. The case arises from the sale of a seasonally operated ranch, the condition of a critical access bridge, and an escrow arrangement intended to fund inspections, tests, and any necessary repairs. When escrowed funds were released without the buyers’ consent, Holloway & Hoskin sued both the seller (Hidden Creek Outfitters) for breach of contract and covenant of good faith and the escrow agent (Park County Title) for breach of contract and fiduciary duty. The Supreme Court affirmed the judgment for nominal damages and upheld the district court’s discretionary denial of attorney’s fees.

Summary of the Judgment

The district court found both Hidden Creek and Park County Title breached their contractual or fiduciary duties but that Holloway & Hoskin failed to prove actual damages with reasonable certainty. Only nominal damages ($100) were awarded.
The sales agreement, a bridging addendum, and a consent-to-hold escrow agreement contemplated that inspections and any required repairs would be funded from $200,000 in escrow—but no single report conclusively identified repairs as “necessary or required.”
Engineering inspections recommended load postings (7-ton then 3-ton) and non-urgent maintenance, but none mandated immediate repair under the contract terms.
The Supreme Court held that where contractual obligations as to repairs were contingent on a third-party (Forest Service or engineer) determination, plaintiffs must prove the repairs were indeed “necessary or required” before claiming damages.
Because Holloway & Hoskin could not segregate which repairs their own final contractor performed were contractually required, the court affirmed only nominal damages and declined to award attorney’s fees, exercising equitable discretion.

Analysis

Precedents Cited

Robinson v. Black (2025 WY 25): Holdings that contract damages “must be proven with a reasonable degree of certainty” and cannot be based on speculation.
Summit Construction v. Koontz (2024 WY 68): Reaffirmation that courts may award only nominal damages when “no actual damages are proven.”
WSP, Inc. v. Wyoming Steel Fabricators & Erectors, Inc. (2007 WY 80): Endorsing the rule against conjectural awards; damages require factual support.
Goforth v. Fifield (2015 WY 82): Authorizing nominal damages where the breach is established but actual loss is not.
Ruby Drilling Co. v. Duncan Oil Co. (2002 WY 85): Standard of appellate review for factual findings—“clearly erroneous” test.
Circle C Res. v. Hassler (2023 WY 54) & Stafford v. JHL, Inc. (2008 WY 128): Discretionary control over contractual fee-shifting provisions under the American Rule.

Legal Reasoning

The Court began by reaffirming the foundational principle that contract damages are remedial and designed to place the injured party in the position they would have occupied absent the breach (Crouch v. Cooper, 2024 WY 98). To obtain such relief, plaintiffs must identify with reasonable certainty both the breach and a quantifiable loss flowing directly from that breach (Robinson v. Black).

Here, the Sales Agreement and its Addendum set aside $200,000 in escrow to pay for (1) a “fracture critical inspection,” (2) a load rating test, and (3) “any repairs deemed necessary by Engineering Associates and/or the U.S.D.A. Forest Service.” The Consent to Hold escrow funds added that release of the balance required agreement by both seller and buyer and Forest Service approval of the bridge condition. Although Engineering Associates, Engineering Operations, and Alfred Benesch & Company inspected the bridge, none issued a binding directive that any single repair was mandatory as a condition of permit transfer. Instead, they recommended load postings (7-ton, then 3-ton) and medium-priority maintenance steps.

Holloway & Hoskin later contracted separately (CC&G) to rebuild the bridge to a 16-ton rating at a cost of $194,799.64. The district court held—and the Supreme Court agreed—that this outlay did not mirror what the original escrow contracts required (only “necessary or required” repairs) and thus failed the certainty requirement. Absent a conclusive third-party mandate, any repairs undertaken by the buyers were voluntary upgrades, not contractually compensable losses.

On attorney’s fees, the Court noted Wyoming’s adherence to the American Rule: each party ordinarily bears its own fees unless a contract or statute provides otherwise. Although the Sales Agreement contained a fee-shifting provision for enforcement, the district court—in a reasoned exercise of its equitable discretion—declined to award fees to either side, observing fault and miscommunication on both sides. The Supreme Court found no abuse of discretion in that balancing.

Impact

This decision underscores two key guidelines for future Wyoming contract litigation:

Damages Certainty: When contract performance hinges on a third-party determination of “necessary” work, plaintiffs must introduce the determinative report or directive. Absent a clear mandate, courts will not speculate about what portion of a plaintiff’s remedial outlay corresponds to a contractual obligation.
Equitable Fee-Shifting: Even with a contractual right to attorney’s fees, trial courts retain broad discretion to deny or limit recovery when equitable considerations—shared fault, miscommunication, or complexity—make a full fee award unjust.

Contract drafters in Wyoming should therefore define with precision any third-party triggers for repair obligations and specify the scope of recoverable costs. Litigants should be prepared to offer detailed evidence connecting their expenditures to the contract’s exact requirements.

Complex Concepts Simplified

Nominal Damages: A token sum (often $100) awarded when a breach is proven but actual loss cannot be clearly measured.
Reasonable Certainty: A burden of proof standard requiring evidence that is specific and factual—not speculative or conjectural—to support a damages claim.
Implied Covenant of Good Faith and Fair Dealing: A duty inherent in every contract that parties must not undermine the agreed exchange of performance; not a license to claim damages absent a formal breach of measurable terms.
American Rule on Fees: Each party pays its own attorney’s fees unless a contract or statute clearly shifts fees to the other side; even then, courts can adjust or deny the award on equitable grounds.

Conclusion

The Wyoming Supreme Court’s decision in Holloway & Hoskin v. Hidden Creek Outfitters reaffirms the requirement that contract damages must be tied to a clear, third-party determination of obligations where the contract so provides. It also confirms the trial court’s discretion to grant or withhold attorney’s fees under a contractual fee-shifting clause. Going forward, contracting parties should precisely define the conditions that trigger allocable payments from escrow or deposits, and litigants must marshal firm evidence of both breach and quantifiable loss. The ruling will guide Wyoming courts and practitioners in drafting enforceable provisions and in presenting—or defending against—claims for repair costs and fees in future breach of contract actions.