Thomas Gaines, Individually and Derivatively on Behalf of Gaines-Gentry Thoroughbreds, LLC v. Hal Price Headley, III, as Administrator of the Estate of Olin Gentry

CourtCourt of Appeals of Kentucky
DecidedDecember 21, 2023
Docket2023 CA 000421
StatusUnknown

This text of Thomas Gaines, Individually and Derivatively on Behalf of Gaines-Gentry Thoroughbreds, LLC v. Hal Price Headley, III, as Administrator of the Estate of Olin Gentry (Thomas Gaines, Individually and Derivatively on Behalf of Gaines-Gentry Thoroughbreds, LLC v. Hal Price Headley, III, as Administrator of the Estate of Olin Gentry) is published on Counsel Stack Legal Research, covering Court of Appeals of Kentucky primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

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Thomas Gaines, Individually and Derivatively on Behalf of Gaines-Gentry Thoroughbreds, LLC v. Hal Price Headley, III, as Administrator of the Estate of Olin Gentry, (Ky. Ct. App. 2023).

Opinion

RENDERED: DECEMBER 22, 2023; 10:00 A.M. NOT TO BE PUBLISHED

Commonwealth of Kentucky Court of Appeals NO. 2023-CA-0421-MR

THOMAS GAINES, INDIVIDUALLY AND DERIVATIVELY ON BEHALF OF GAINES-GENTRY THOROUGHBREDS, LLC APPELLANT

APPEAL FROM FAYETTE CIRCUIT COURT v. HONORABLE THOMAS L. TRAVIS, JUDGE ACTION NO. 18-CI-00091

HAL PRICE HEADLEY, III, AS ADMINISTRATOR OF THE ESTATE OF OLIN GENTRY APPELLEE

OPINION AFFIRMING

** ** ** ** **

BEFORE: CETRULO, COMBS, AND EASTON, JUDGES.

CETRULO, JUDGE: Appellant Thomas Gaines (“Gaines”) appeals three orders

dismissing all of his claims against his former business partner for alleged breaches

of contractual fiduciary duties and statutory obligations of good faith and fair

dealing. Finding no error, we affirm the Fayette Circuit Court (“trial court”). I. BACKGROUND

In 2018, Gaines filed a complaint against his co-manager, Olin Gentry

(“Gentry”), at Gaines-Gentry Thoroughbreds, LLC1 (“GGT”). The claims in the

complaint span 17 years, during which the company went through multiple

comprehensive changes in management. In his complaint, Gaines alleged Gentry2

breached his statutory and contractual duties, committed fraud by omission,

misappropriated GGT assets, and concealed “self-serving” transactions.

In 1994, Gaines’s father first incorporated John R. Gaines

Thoroughbreds, LLC to deal with a wide variety of equine-industry-related

business interests. For purposes of our discussion, after Gaines’s father left the

company, it evolved into GGT with Gaines and Gentry serving as co-managers.

Through the years, the parties signed various contractual agreements: (1) an

employment agreement signed in 1997; (2) a succession agreement signed in 2000;

(3) a settlement agreement signed in 2006; and (4) an operating agreement signed

in 2007. The interpretation of those contracts forms the foundation of this action.

1 Gaines Gentry Thoroughbreds, LLC, has evolved as a company through the years with various leadership, ownership, member composition, and structural formation. The company names have included Gaines-Gentry, LLC; Gaines-T-Breds, LLC; John R. Gaines Thoroughbred, LLC; and Gaines-Gentry Thoroughbreds, LLC, but for clarity we shall use “GGT” throughout, unless distinction is necessary. 2 Shortly after the filing, Gentry passed away and Gaines continued the action against his estate, represented by Hal Price Headley, III, as administrator of Gentry’s estate.

-2- In 1997, Gentry signed an Employment Agreement (“1997

Employment Agreement”) with GGT.3 The 1997 Employment Agreement

imposed upon Gentry fiduciary and reporting obligations. In relevant part, the

contract stated:

During the Term, [Gentry] shall not engage in any activity which is (or has the potential to be) in conflict with the interests of [GGT] or [GGT’s] Affiliates or which is otherwise inconsistent with the highest fiduciary standards and duties (including, but not limited to, the fiduciary duty of loyalty generally imposed upon employees, officers, and directors of business corporations). In this regard, but not by way of limitation of [Gentry’s] general fiduciary duties, [Gentry] shall not engage in any paid or unpaid work activities which are not for the benefit of [GGT]. . . . [Gentry] shall not engage in, invest in, purchase, acquire, trade, exchange, sell, syndicate, breed or otherwise possess, receive, or otherwise deal in or with respect to any equity, creditor, profit, cash flow, distribution, compensatory, or other interests in or with respect to any equine interests, participations, investments, shares, fractional interests, foal sharings, breeding rights, commissions or other rights or benefits, whether direct or indirect through any one or more corporations, partnerships, limited liability companies, trusts, or other entities, individuals (whether or not related), third party arrangements, or otherwise, except [those equine interests approved by the Board and/or currently owned and reported]. . . . Furthermore, [Gentry] shall be obligated to immediately present to [GGT], and permit [GGT] to take, separately or with other, any and all rights, options, or other business or investment opportunities with respect to equine interests and activities of which [Gentry] has knowledge or which are presented to or otherwise come to [Gentry’s] attention at any time during the Term.

3 More specifically, with John R. Gaines Thoroughbreds, LLC.

-3- During the relevant timeframe – although the exact dates are unclear

from the record – Gentry solely owned Geneli Thoroughbreds, Inc. (“Geneli”).

The record reflects that Gaines was aware – he claimed “vaguely aware” – of

Gentry’s ownership of Geneli, and Gaines admitted he had received commission

checks from Geneli.

In 2000, as a condition of becoming President and CEO of GGT,

Gentry signed a Succession Agreement (“2000 Succession Agreement”) which

passed control of GGT to Gaines and Gentry from Gaines’s father. The 2000

Succession Agreement created a management board made up of Gentry, Gaines,

and Gloria (Gaines’s sister), and it repeated (as similarly detailed in the 1997

Employment Agreement), that the three board members must present any business

opportunities which become available to them by reason of their relationship with

the company to the other principals.

All potential equine transactions and equine-industry- related investment or business opportunities which are developed by, or become available to, [Gentry], Gloria or [Gaines], and any other potential investment or business opportunities which become available to [Gentry], Gloria or [Gaines], directly or indirectly by reason of his or her relationship with [GGT] and its activities, shall be presented to [GGT] and the other [members], and [GGT] or all three of [Gentry], Gloria or [Gaines], as the cause may be, shall have the right and privilege to elect to take and pursue such transaction or opportunity, with all economic benefits therefrom inuring to the benefit of [GGT] . . . . None of [Gentry], Gloria or [Gaines], will be

-4- permitted to individually invest or pursue equine transactions or equine-industry-related investment or business opportunities if [GGT] or the other two [members] refuse or fail to take or pursue such transaction or opportunity, unless agreed to by all three of them.

However, Gaines, Gentry, and Gloria were unable to manage GGT as

a cohesive unit, and in 2003 Gaines filed a lawsuit against Gloria seeking to

remove her from GGT. In 2006, Gaines and Gloria reached a settlement (“2006

Settlement Agreement”) that removed Gloria from the company but was silent as

to any management issues.

In 2007, Gaines, Gentry, and Gaines’s mother, Joan Gaines (“Joan”),

signed a Second Amended Operating Agreement that was backdated to January

2006 (“2006 Operating Agreement”). While both Gaines and Gentry were

designated as “Managers,” Gentry handled the active management of GGT as

operating manager. The 2006 Operating Agreement did not contain language

requiring the members to share equine interests with each other or GGT. In fact,

the 2006 Operating Agreement waived many fiduciary duties and superseded prior

contracts.

5.7 Fiduciary Duties of Members. To the fullest extent permitted by Law, each Member (the “Waiving Member”) hereby agrees to (a) waive any fiduciary duties or personal liability that any other Member may have to the Company or such Waiving Member, whether such duties or liability would otherwise arise in such other Member’s capacity as a Member, Manager or officer, and (b) eliminate any

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Thomas Gaines, Individually and Derivatively on Behalf of Gaines-Gentry Thoroughbreds, LLC v. Hal Price Headley, III, as Administrator of the Estate of Olin Gentry, Counsel Stack Legal Research, https://law.counselstack.com/opinion/thomas-gaines-individually-and-derivatively-on-behalf-of-gaines-gentry-kyctapp-2023.