Contract analysis

I. PURPOSE AND SCOPE OF MEMORANDUM The purpose of this memorandum is to document the results of the conflict of interest check conducted in connection with the proposed engagement of Jonathan R. Caldwell for comprehensive generational estate planning services. This memorandum sets forth the parties searched, the methodology employed, the results of the conflict search, and the conclusions and recommendations of the u

II. MATTER DESCRIPTION Calderwood & Harkness LLP has been asked to design and implement a comprehensive generational estate plan for Jonathan R. Caldwell, a sixty-seven-year-old resident of New York, New York, with an estimated gross estate of approximately three hundred million dollars ($300,000,000). Mr. Caldwell's estate is principally comprised of liquid investment securities, limited partnership interests and ca

1. Three Grantor Retained Annuity Trusts (GRATs): (a) Caldwell 2023 Securities GRAT ("GRAT A") — to be funded with publicly traded securities and other liquid investment assets; (b) Caldwell 2023 Realty GRAT ("GRAT B") — to be funded with membership interests in Stonecrest Realty Holdings LLC; (c) Caldwell 2023 Carried Interest GRAT ("GRAT C") — to be funded with carried-interest positions in Caldwell Ridgeline Fund

2. Caldwell Family Dynasty Trust — an irrevocable, multi-generational trust with Delaware situs, designed to hold remainder assets passing from the GRATs and additional transferred assets for the benefit of Mr. Caldwell's descendants in perpetuity under Delaware's rule against perpetuities.

3. The Caldwell Family Foundation — a private foundation to be organized as a New York not-for-profit corporation and to apply for tax-exempt status under Internal Revenue Code § 501(c)(3). Eleanor V. Caldwell will serve as co-founder, and the foundation's initial board of directors will include family members and an independent director.

4. Caldwell Family Insurance Trust (ILIT) — an irrevocable life insurance trust with Delaware situs, to be the owner and beneficiary of a $15,000,000 second-to-die universal life insurance policy issued by Beacon Life Assurance Company on the joint lives of Jonathan and Eleanor Caldwell.

5. Amendment and Restatement of the Caldwell Revocable Trust — originally established on October 3, 2010. The existing trust instrument will be amended and restated in its entirety to reflect updated dispositive provisions, updated fiduciary appointments, and coordination with the new estate planning structures.

6. New Pour-Over Will — a new last will and testament for Jonathan R. Caldwell, providing for the disposition of probate assets to the Caldwell Revocable Trust (as amended and restated).

7. Powers of Attorney — new durable general power of attorney and statutory gifts rider under New York General Obligations Law.

8. Health Care Directives — new health care proxy and living will under New York Public Health Law. The engagement team assigned to this matter is as follows:

III. PARTIES SEARCHED The following parties were identified as relevant to the proposed engagement and were searched through the firm's central conflicts database. Each party is listed with all identifying information available as of the date of this memorandum. A. Client and Immediate Family

1. Jonathan R. Caldwell — Client / Grantor Date of Birth: March 14, 1956 Residence: 418 East 72nd Street, Apt. 14A, New York, NY 10021 SSN (last four digits): 4781 Occupation: Founder and former Managing Partner, Caldwell Ridgeline Capital LLC Role in Matter: Client; grantor of all proposed trust structures; co-founder of proposed private foundation; testator of proposed pour-over will; principal of proposed powers o

2. Eleanor V. Caldwell (née Whitmore) — Spouse Date of Birth: September 22, 1958 Residence: 418 East 72nd Street, Apt. 14A, New York, NY 10021 SSN (last four digits): 6203 Occupation: Former partner, Whitmore-Langdon Gallery (retired) Role in Matter: Co-grantor of the proposed private foundation; named beneficiary of certain trust structures; co-insured under the proposed second-to-die life insurance policy. Eleanor

3. Thomas R. Caldwell — Son Date of Birth: June 7, 1985 (Age 38) Residence: 55 Perry Street, Unit 3, New York, NY 10014 Occupation: Vice President of Acquisitions, Meridian Crest Partners LLC Role in Matter: Named beneficiary of various trust structures; designated successor trustee of certain trusts; designated director of the proposed Caldwell Family Foundation.

4. Katherine C. Hartfield (née Caldwell) — Daughter Date of Birth: November 19, 1987 (Age 35) Residence: 210 Briarcliff Lane, Greenwich, CT 06830 Occupation: Freelance interior designer Role in Matter: Named beneficiary of various trust structures; designated director of the proposed Caldwell Family Foundation. Maiden Name Searched: Caldwell

5. Olivia G. Caldwell — Daughter Date of Birth: April 2, 1993 (Age 30) Residence: 1240 North Dearborn Street, Apt. 807, Chicago, IL 60610 Occupation: Associate, Linden & Fairchild LLP (Chicago, Illinois); practicing environmental law Role in Matter: Named beneficiary of various trust structures; designated director of the proposed Caldwell Family Foundation.

6. Dr. Sarah P. Caldwell (née Brennan) — Daughter-in-law (spouse of Thomas R. Caldwell) Occupation: Physician Role in Matter: Spouse of beneficiary; potential contingent beneficiary. Searched as related party. Maiden Name Searched: Brennan

7. Dr. Andrew W. Hartfield — Son-in-law (spouse of Katherine C. Hartfield) Occupation: Orthopedic surgeon, Preswick Medical Center Role in Matter: Spouse of beneficiary; potential contingent beneficiary. Searched as related party.

8. Minor Grandchildren (searched by family name) (a) James W. Hartfield — Age 8 (child of Katherine and Andrew Hartfield) (b) Charlotte M. Hartfield — Age 5 (child of Katherine and Andrew Hartfield) (c) Lucas T. Caldwell — Age 3 (child of Thomas and Sarah Caldwell) (d) Nora E. Caldwell — Age 1 (child of Thomas and Sarah Caldwell) Role in Matter: Named beneficiaries of dynasty trust and other trust structures; conting

9. Caldwell Ridgeline Capital LLC Entity Type: Delaware limited liability company Address: 280 Park Avenue, 35th Floor, New York, NY 10017 Description: Mr. Caldwell's former asset management firm, managing approximately $2.1 billion in assets under management. Mr. Caldwell retired from active management but retains economic interests in the firm's legacy funds. Key Contact: Gregory S. Fenton, Chief Financial Officer

10. Caldwell Ridgeline Fund IV LP Entity Type: Delaware limited partnership Vintage: 2015 Description: Mr. Caldwell holds a limited partner interest valued at approximately $12,000,000. Role in Matter: LP interest is an estate asset to be addressed in the plan.

11. Caldwell Ridgeline Fund V LP Entity Type: Delaware limited partnership Vintage: 2018 Description: Mr. Caldwell holds a limited partner interest valued at approximately $14,000,000. Role in Matter: LP interest is an estate asset to be addressed in the plan.

12. Caldwell Ridgeline Fund VI LP Entity Type: Delaware limited partnership Vintage: 2021 Description: Mr. Caldwell holds a carried-interest position valued at approximately $12,000,000. Role in Matter: Carried-interest position is proposed to be transferred to GRAT C.

13. Stonecrest Realty Holdings LLC Entity Type: New York limited liability company Address: 330 Madison Avenue, Suite 2401, New York, NY 10017 Description: Mr. Caldwell's real estate holding company, which owns eleven commercial and residential properties located in New York, New Jersey, and Connecticut, with a total estimated fair market value of approximately $134,000,000. Key Contact: Robert M. Sinclair, Chief Ope

14. Meridian Crest Partners LLC Entity Type: Delaware limited liability company (New York-based) Description: Mid-market real estate private equity firm. Employer of Thomas R. Caldwell. Role in Matter: Searched as a related entity due to the employment relationship of Thomas R. Caldwell. Calderwood & Harkness does not represent Meridian Crest Partners LLC in any capacity. C. Proposed Trusts and Foundation (New Entiti

15. Caldwell 2023 Securities GRAT (GRAT A) — Proposed irrevocable trust to be governed by New York law.

16. Caldwell 2023 Realty GRAT (GRAT B) — Proposed irrevocable trust to be governed by New York law.

17. Caldwell 2023 Carried Interest GRAT (GRAT C) — Proposed irrevocable trust to be governed by New York law.

18. Caldwell Family Dynasty Trust — Proposed irrevocable trust with Delaware situs, to be governed by Delaware law.

19. Caldwell Family Insurance Trust (ILIT) — Proposed irrevocable trust with Delaware situs, to be governed by Delaware law.

20. The Caldwell Family Foundation — Proposed New York not-for-profit corporation; to apply for recognition of tax-exempt status under Internal Revenue Code § 501(c)(3).

21. Caldwell Revocable Trust — Existing revocable trust originally established on October 3, 2010, by Jonathan R. Caldwell as grantor. The trust instrument is to be amended and restated in its entirety as part of this engagement. D. Institutional Trustee

22. Northgate Trust Company of Delaware Entity Type: Delaware trust company Address: 1201 North Market Street, Suite 1600, Wilmington, DE 19801 Description: Proposed institutional co-trustee of the Caldwell Family Dynasty Trust and proposed administrative trustee of the Caldwell Family Insurance Trust (ILIT). Key Contact: Philip A. Rossiter, Senior Vice President, Trust Administration Role in Matter: Institutional fi

23. Pemberton, Locke & Strauss LLP Entity Type: New York limited liability partnership (law firm) Address: 405 Lexington Avenue, 26th Floor, New York, NY 10174 Description: Retained as independent counsel to Eleanor V. Caldwell in connection with the estate plan. Key Contact: Rachel F. Dunlap, Esq., Partner, Private Client Role in Matter: Independent counsel to the client's spouse; engaged at Calderwood & Harkness's

24. Ridgewell & Thorn LLP Entity Type: Delaware limited liability partnership (law firm) Address: 1000 North King Street, Suite 300, Wilmington, DE 19801 Description: Delaware counsel to Northgate Trust Company of Delaware. Key Contact: Margaret A. Colvin, Esq., Partner, Fiduciary Practice Role in Matter: Local Delaware counsel to the institutional trustee; aligned party.

25. Linden & Fairchild LLP Entity Type: Illinois limited liability partnership (law firm) Address: Chicago, Illinois Description: National law firm with offices in Chicago and elsewhere. Employer of Olivia G. Caldwell, who practices in the firm's environmental law department. Role in Matter: Not engaged in this matter in any capacity. Searched as a related entity solely due to the employment relationship of Olivia G.

26. Strathmore Corporation & Greaves LLP Entity Type: New York limited liability partnership (accounting and tax advisory firm) Address: 600 Third Avenue, 28th Floor, New York, NY 10016 Description: Mr. Caldwell's personal accountants and tax advisors, responsible for the preparation of his individual and entity-level tax returns and providing ongoing tax planning advice. Key Contact: Martin J. Prescott, CPA, Senior

27. Havensbrook Wealth Advisors LLC Entity Type: Delaware limited liability company (New York-based) Address: 900 Third Avenue, 18th Floor, New York, NY 10022 Description: Mr. Caldwell's financial advisor and investment manager, providing investment management, financial planning, and family office services. Key Contact: Diana R. Linden, CFP®, Managing Director, Family Office Services Role in Matter: Financial adviso

28. Ashford Valuation Group LLC Entity Type: New York limited liability company Address: 1120 Avenue of the Americas, Suite 3500, New York, NY 10036 Description: Independent qualified appraisal firm retained to provide fair market value appraisals of illiquid and hard-to-value assets, including Caldwell Ridgeline LP and carried-interest positions, Stonecrest Realty Holdings LLC membership interests, and art and colle

29. Glenmore Insurance Brokerage LLC Entity Type: New York limited liability company Address: 44 Wall Street, Suite 1200, New York, NY 10005 Description: Insurance brokerage firm engaged to procure the life insurance policy to be held by the ILIT. Key Contact: Nathan C. Freed, Senior Vice President, Private Client Division Role in Matter: Insurance broker; procuring the $15,000,000 second-to-die universal life insura

30. Beacon Life Assurance Company Entity Type: Connecticut domiciled life insurance company Address: 100 Constitution Plaza, Hartford, CT 06103 Description: Proposed issuer of the $15,000,000 second-to-die universal life insurance policy. Role in Matter: Insurance carrier; product provider.

I. Foundation Independent Director

31. Dr. Margaret P. Elsworth Title: Professor Emerita, Columbia University; philanthropic advisor Role in Matter: Proposed independent director of The Caldwell Family Foundation. Dr. Elsworth is a personal acquaintance of the Caldwell family who has served in advisory capacities to several private foundations in the New York philanthropic community.

IV. CONFLICT SEARCH METHODOLOGY The conflict of interest search was conducted using Calderwood & Harkness LLP's central conflicts database (the "Conflicts System"), which is maintained by the firm's Conflicts Department and serves as the firm's comprehensive repository of all current and former client information, adverse party information, related party information, and engagement data across all practice groups and

V. RESULTS OF CONFLICT SEARCH A. No Direct Conflicts Identified Based on the searches described in Section IV above, no current or former client representations were identified that would create a direct conflict of interest under New York Rules of Professional Conduct Rule 1.7 (Conflict of Interest: Current Clients) or Rule 1.9 (Duties to Former Clients) with respect to any of the parties listed in Section III of th

VI. ENGAGEMENT TEAM CONFLICT REVIEW In addition to the party-level conflict search described in Sections IV and V above, each member of the Calderwood & Harkness LLP engagement team was individually reviewed for potential conflicts of interest, including personal or financial interests in any party or entity listed in Section III, familial relationships with any searched party, and any other circumstance that could g

VII. CONCLUSION AND CLEARANCE Based on the comprehensive conflict of interest check described in this memorandum, including the search of the firm's central conflicts database, the review of prior engagements involving searched parties, the analysis of potential multiple-representation issues, the analysis of the proposed trust protector designation, and the individual conflict review of each engagement team member,

1. Sole Client Identification. The engagement letter, to be dated February 15, 2023, must clearly and unambiguously identify Jonathan R. Caldwell as the sole client of Calderwood & Harkness LLP in this matter. The engagement letter must include an express disclaimer of any attorney-client relationship between the firm and any other member of the Caldwell family, including Eleanor V. Caldwell, Thomas R. Caldwell, Kath

2. Independent Counsel for Eleanor V. Caldwell. Eleanor V. Caldwell must retain and be represented by independent counsel for her interests in the estate plan. Mrs. Caldwell has engaged Pemberton, Locke & Strauss LLP (Rachel F. Dunlap, Partner) for that purpose. The engagement letter should confirm this arrangement and note that Calderwood & Harkness LLP does not represent Mrs. Caldwell.

3. Informed Consent re: Trust Protector Designation. Informed consent must be obtained from Jonathan R. Caldwell, confirmed in writing, regarding Victoria Chambers's proposed dual role as the Responsible Partner on the engagement and the designated trust protector of the Caldwell Family Dynasty Trust. The engagement letter must describe the scope and non-fiduciary character of the trust protector role and the firm's

4. Written Disclosure to Beneficiary Family Members. A written disclosure must be provided to Thomas R. Caldwell, Katherine C. Hartfield, and Olivia G. Caldwell clarifying that Calderwood & Harkness LLP represents Jonathan R. Caldwell and does not represent them individually, and that they are free to consult independent counsel regarding any aspect of the estate plan that affects their interests. It is recommended t

VIII. APPROVAL I have reviewed this Conflict Check Memorandum and the results of the conflict of interest search conducted in connection with Matter No. 1034-00004 (Generational Estate Plan for Jonathan R. Caldwell). Based on my review, I approve the firm's acceptance of the proposed engagement, subject to the conditions set forth in Section VII above. The approved memorandum shall be placed in the matter file (1034-