Dillon L. Roberts
PARTNER
- TRUSTS, ESTATES & TAX
- (772) 758-0196
- [email protected]
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Dillon L. Roberts represents clients in connection with complex estate and trust planning and administration, federal tax reporting, and wealth transfer planning. Dillon regularly advises clients with estates exceeding federal tax exemption thresholds, including filing of estate and gift tax returns and preserving valuable tax exemptions for future generations. He has represented trustees and beneficiaries in the administration, modification, and restructuring of irrevocable trusts, including strategies like decanting, severance, and nonjudicial settlement agreements.
His practice leverages sophisticated estate planning techniques designing and implementing trusts, through the establishment of special-purpose entity structures, and optimizing tax-efficient transfer strategies tailored to unique family dynamics and long-term wealth preservation. He also assists clients with business succession planning and the restructuring of operating businesses and real estate investments, often coordinating with investment advisors, accountants, valuation experts, and family office professionals.
- Elon University (B.S., 1998)
- Florida Atlantic University (MBA, 2002)
- University of Florida, College of Law, (J.D., 2011)
- University of Florida, College of Law, (LL.M., Taxation, 2014)
- Board Certified Specialist in Tax Law
- AV Rated, Martindale-Hubbell
- Super Lawyers, “Rising Star”
- US Army Veteran
- The Florida Bar
- Indian River County Bar Association
- Florida Bar, Real Property, Probate and Trust Law Sections
- Indian River County Estate Planning Council
- Dillon L. Roberts, Presenter “Estate Administration of Closely Held Business Interests” Tax Section of the Florida Bar (Fall Meeting. September 29, 2023).
- Dillon L. Roberts, Presenter “Business Succession Planning” Indian River County Estate Planning Council (October 19, 2023).
- Former US Army Captain
Notable Representations
- Represented multiple fiduciaries filing of IRS Form 706 (estate tax return) for estates in excess of $13.9 million as well as filing to preserve decedent’s unused exemption amounts to shelter future estate taxes.
- Assisted multiple clients in connection with administration irrevocable trusts, including modification (judicially and nonjudicially), nonjudicial settlement agreements, decanting assets to new trust, and severance of trust into one or more subtrust (for GST tax purposes or for interests of trustee and beneficiary).
- Represented fiduciary in connection with Florida trust modification to identify mixed GST Tax inclusion ratio and outline aspects of reporting; assist with severance and subsequent administration of resulting trusts.
Represented fiduciary surviving spouse to identify disclaimer planning to achieve income tax cost basis adjustment under IRC Section 1041 reducing overall tax by $3 million.
Represented fiduciaries in obtaining release of federal tax liens on estate property to allow for sale and diversification of illiquid assets (IRS Form 4422 and IRS Form 14135).
Represented trustees of multi-generational dynasty trust in connection with Florida administration to include management of going concern assets, interpretation of terms, preservation of “grandfathered” GST tax exempt status, and fiduciary succession options.
Represented multiple surviving spouses in connection with statutory entitlements under Florida law together with Florida homestead issues in connection with estate administration.
- Represented multiple clients in connection with reporting lifetime taxable gifts (IRS Form 709) as well as adequate disclosure filings to initiate limitations periods on leveraged or discounted transfers with no gift component.
- Prepared IRS Private Letter Ruling to request relief for terminated election under IRC Section 1362 (for S corporation with unpermitted trust shareholder).
- Represented clients in connection with the filing of a “late” allocation of client GST exemption to non-exempt trust (with inclusion ratio of 1, resulting in zero inclusion ratio) maximizing the use of remaining exemption without additional transfers of assets.
- Advised multiple fiduciaries in connection with gift and estate tax reporting in connection with difficult-to-value assets such as going concern businesses, private equity, promissory notes and other financial instruments.
- Represent family in connection with aspects of structuring multi-generational estate plan to address transfer tax and income tax efficiencies; work with family client’s firm relationship manager to coordinate business governance matters, life insurance structuring for liquidity, reporting items with family CPAs, and overall financial structuring with family investment advisors.
- Represent multiple clients with federal taxable estates in excess of $100 million structure estate plans (using trusts and special purpose entities) to achieve overall transfer goals in a tax efficient manner.
- Assist multiple clients with wealth in excess of available federal estate tax exemptions ($13.9 million) structure plans to maximize preservation of assets and maximize transfer of inter-generational wealth and navigate blended family dynamics.
- Structured estate plan to establish non-qualified terminal interest property trust and specific funding of low basis assets to achieve full basis adjustment at death of first spouse (reduction in overall tax in excess of $1 million).
- Represented multiple estate planning clients in connection with preparation of (i) grantor retained annuity trust (GRATs) (including cash funding portion for illiquid assets and interrelated calculations for annuity payments); (ii) irrevocable life insurance trusts; (iii) GST exempt and GST nonexempt irrevocable trusts for descendants; and (iv)
- Assisted family clients in restructuring (and ultimately divesting portions of) multi-tiered automotive organizational structure while preserving going concern business attributes and avoiding application of transfer tax and income tax recognition.
- Work with multiple clients to structure special purpose entities (consolidating assets and management features) to leverage available valuation discounts, preserve elements of management and control, and achieve family objectives of preservation of wealth.
- Prepared and implemented member divestment strategy to allow client to recognize current capital loss (to apply against current tax year gain) notwithstanding cancellation of debt and recourse loan classification of member loan to underlying partnership.
- Assisted family clients spinoff portions of real estate development going concern, deferring gain under installment structures and providing opportunities to achieve long-term investment strategies on a tax-efficient basis.
- Represented client in connection with funding various related and contiguous parcels of recreational real property to special purpose entities and common fund/ownership entity to allow for subsequent generational use and management, avoiding deed restrictions, and outlining equitable exit strategies for subsequent family lines.
- Assisted multiple clients in preparing organizational documents to establish and administer private foundation, including governing instruments, policies and procedures, and filing IRS Forms 1023 (to confirm exempt status of organization).
- Assisted clients in evaluating transfers to various donor advised funds (characterized as public charities by the Internal Revenue Service) to analyze application of Section 170 available income tax deductions and valuation issues in connection with gift of closely-held equity interests and securities.
- Represented multiple boards of directors in dissolving private foundation corporate structure and distributing assets as required by organizational documents and applicable income tax rules and regulations.
- Represented multiple clients in terminating current retained non-charitable interest in charitable remainder trusts, accelerating overall gift to charity, and calculating additional IRC Section 170 deduction.
