Transferee and Fiduciary Liability for Estate Tax Applied to Second Level Transferee and Fiduciary. United States v. Estate of Kelley, et al., No. 3:17-CV-965-BRM-DEA (D.N.J. Oct. 22, 2020)

By: Ryan Tompkins, Sullivan & Worcester


Lorraine M. Kelley (“Kelley”) died on December 30, 2003.  Kelley’s brother, Richard Saloom (“Saloom”) and Richard J. Lecky were appointed as co-executors of Kelley’s estate.  The executors filed a federal estate tax return for Kelley’s estate reporting a gross estate of approximately $1.7 million, which was adjusted to roughly $2.6 million upon examination by the IRS resulting in an additional tax liability.  Saloom consented to the assessment in June of 2006.  In late 2007, Saloom began making payments toward the tax liability.

Saloom was the sole beneficiary of Kelley’s estate.  By January of 2008, Saloom had distributed the entire estate to himself, although more than $450,000 remained outstanding in federal estate tax due.  Saloom died on March 21, 2008.  The gross value of Saloom’s estate totaled approximately $1.1 million.

Saloom’s daughter, Rose Saloom (“Rose”), was the sole beneficiary and executor of Saloom’s estate.  After Saloom’s death, Rose filed a New Jersey inheritance tax return for Saloom’s estate listing a $456,406 debt for “federal tax” and she made several payments toward the outstanding estate tax liability for Kelley’s estate.  Rose did not, however, retire the entire balance.  Rose instead distributed the remaining assets of Saloom’s estate to herself leaving the estate insolvent.  As of September 2, 2019, the unpaid balance of Kelley’s estate tax liability with accrued penalties and interest was $688,644.


Attorneys from the Tax Division of the United States Department of Justice filed a complaint in federal district court asserting transferee liability and fiduciary liability for the estate tax against Rose, as executor of Saloom’s estate and individually, among other claims and requests for relief.

Section 6324(a)(2) of the Internal Revenue Code imposes personal liability on certain transferees of the decedent’s gross taxable estate when the estate itself fails to pay any estate tax.  The transferee’s liability is limited to the value of property received from the estate.

The federal insolvency statute, 31 U.S.C. § 3713, places personal liability on the executor of an estate who pays the debts of the estate or distributes assets of the estate, before paying a claim of the United States.  This rule is intended to preserve the priority of debts due to the United States.  Personal liability can attach, to the extent of the distribution, if the government establishes that (1) the fiduciary distributed the assets of the estate; (2) the distribution rendered the estate insolvent; and (3) the distribution took place after the fiduciary had actual or constructive knowledge of the liability for unpaid taxes.  See United States v. Tyler, No. 10-1239, 2012 U.S. Dist. LEXIS 34093, at *10 (E.D. Pa. Mar. 13, 2012), aff’d 528 F. App’x 193 (3d Cir. 2013).  Fiduciaries can be deemed to have had constructive knowledge if they had “notice of facts that would lead a reasonably prudent person to inquire as to the existence of the debt owed before making the challenged distribution or payment.”  528 F. App’x at 201 (quoting United States v. Coppola, 85 F.3d 1015, 1020 (2d Cir. 1996)).

Liability of Saloom’s Estate

The court concluded that there was no material dispute of fact as to whether Saloom had knowledge of the tax liability for Kelley’s estate when he intentionally distributed assets from the estate to himself rendering the estate insolvent.  Saloom was therefore personally liable for the estate tax liability of Kelley’s estate.  Thus, the Kelley estate tax liability was a debt due to the United States from Saloom’s estate

Liability of Rose Individually

The court then found that Rose was personally liable as the fiduciary of Saloom’s estate based upon her failure to pay the Kelley estate tax liability out of the assets of Saloom’s estate prior to distributing the estate assets to herself.  In arriving at this conclusion, the court noted that Rose clearly had actual knowledge of the federal estate tax owed by her father, which she listed as “indebtedness” for “federal tax” on the New Jersey inheritance tax return she filed for Saloom’s estate.  Rose also made several payments toward the debt after Saloom’s death.


While the result of this case is not entirely surprising on the facts, it serves as a reminder to practitioners that transferee and fiduciary liability can operate in tandem to extend the reach of the federal insolvency statute beyond the fiduciaries and first order transferees of the estate that generates the tax.  After all, Rose was neither a fiduciary nor a direct transferee of Kelley’s estate and yet the court found her to be personally liable for the entire estate tax due.

Upcoming Trust & Estates Events at the BBA – February 2021

By: Jennifer D. Taddeo, Conn Kavanaugh and Rebecca Tunney, Goulston & Storrs, Communications Committee, Trusts and Estates Section

Upcoming Trust & Estates Section Programs at the BBA this month: 

Charitable Giving Basics for Estate Planners Wednesday, February 3, 2021  This program will provide an introduction to charitable planning. We will discuss the reasons for charitable giving, the types of property that can be used to make a charitable gift, and the techniques that can be used to achieve clients’ charitable goals.

Special Drafting Considerations for Elderly Clients Thursday, February 11, 2021  Attorneys Patricia Keane Martin and Kristin Dzialo will discuss special drafting considerations for practitioners to be mindful of when advising elderly clients.  Specifically, they will discuss language concerning end of life decision-making and care, and the importance of counseling clients on the implications of including or excluding certain powers from their documents with an eye towards protecting the client and achieving his or her planning goals. The discussion will be beneficial both for practitioners new to estate planning and for seasoned estate planners.

Speed Networking with Trusts & Estates Attorneys Tuesday, February 16, 2021   This event gives law students and new lawyers a unique opportunity to meet with several Boston-area trusts & estates attorneys in just one evening. Those who attend this event will have the chance to meet all of our guest attorneys in small groups to learn about lawyering in a pandemic, career paths, and legal opportunities available in Boston.

Remote Execution of Estate Plan Documents: Practicalities, Pitfalls and Best Practices  Monday, February 22, 2021 This program will cover the Remote Notarization Act, which was signed into law by MA Governor Charlie Baker on April 27, 2020.  The speaker will review the requirements of remote notarization in MA for estate planning documents and will also host a “mock remote signing” during the program.

Upcoming Events at the BBA – January 2021

By: Jennifer D. Taddeo, Conn Kavanaugh and Rebecca Tunney, Goulston & Storrs, Communications Committee, Trusts and Estates Section

Upcoming Trust & Estates Section Programs at the BBA this month: 

Modifying Irrevocable Trusts: Decanting, Non-Judicial Settlement Agreements and other Trust Amendment Alternatives   Wednesday, January 6, 2021  This program will provide an introduction to various methods for modifying an irrevocable trust, including how and when to consider: (1) Modifications under the Massachusetts Uniform Trust Code, (2) reformations, (3) non-judicial settlement agreements, and (4) decanting.

Breach of Fiduciary Duty Litigation: Superior Court versus Probate & Family Court   Wednesday, January 13, 2021  A panel of probate litigators will share insights for bringing fiduciary duty claims and defending those claims, whether brought in Superior Court or the Probate & Family Court. The panelists will also explore litigation tactics applicable to each court as well as alternate dispute resolution and settlement opportunities.

Trusts & Estates Mid-Year Review    Tuesday, January 19, 2021   An annual event not to be missed, the Trusts & Estates Mid-Year Review covers recent federal and state case law, legislation and tax law matters. This year’s program will touch on:

  • New Developments Committee:  The committee will review recent estate planning and administration cases.
  • Public Policy Committee:  The presentation will include an overview of recent and pending legislation.
  • Tax Law Updates Committee:  The committee will report on important updates regarding the Internal Revenue Code, federal tax law, recent cases, private letter rulings, charitable planning updates, retirement cases and other interesting developments.

2020-2021 Income Tax Charitable Deduction Changes

By: Keirsa K. JohnsonHemenway & Barnes LLP

Until a few days ago, Massachusetts taxpayers were scheduled to be able to take state income tax deductions for charitable contributions, for the first time since 2001, starting in January 2021.  As a result of the recent budgeting process, however, allowance of those deductions has been postponed until 2022.


In 2000, voters approved a ballot initiative to reduce the state’s income tax rate from 5.95% to 5.00% by 2003.  One year after implementation, citing budget shortfalls that forced cuts to essential services, the legislature repealed that change and instead enacted legislation that reduced the income tax rate by .05% each year in which certain economic triggers were met, until the income tax rate hit 5.00%.  As part of that legislation, charitable deductions from income were also suspended until the 5.00% tax rate was reached.  (Notably, that legislation also decoupled the Massachusetts estate tax from the federal estate tax regime.  See TIR 02-18, Tax Changes Contained in “An Act Enhancing State Revenues” and Related Acts.)

Taxpayers with excess charitable contribution amounts in 2001 were permitted to carry those amounts forward five years but, since a 5.00% tax rate was not reached and the charitable deduction was not reinstated by 2006, those deductions were lost.

In December of 2019, the Baker/Polito administration announced that the final rate reduction requirements had been met, that the income tax rate for 2020 would be 5.00%, and that starting in 2021 taxpayers would be able to claim a deduction for charitable contributions.  The deduction was expected to cost the Commonwealth an estimated $64 million in Fiscal Year 2021, and up to $300 million in full fiscal years after that. 

Given the significant budget deficit caused by the COVID-19 response, however, some proposed delaying the reintroduction of the charitable deduction until 2022.  On December 11, 2020, Governor Baker signed budget legislation doing just that.

Looking Forward

When the charitable deduction becomes available (assuming no change to current law), it will be available only to individuals—including “non-itemizers” who take the standard deduction on their federal income tax returns—and will be taken against Part B adjusted gross income.  No deduction will be allowed for the contribution of household goods or used clothing.  G.L. c. 62, § 3.B(a)(13).

Federal Context

The charitable deduction for federal income taxes was also changed for 2020 under the Coronavirus, Aid, Relief, and Economic Security Act (“CARES Act”).  Under the Tax Cuts and Jobs Act (“TCJA”) of 2017, individuals were allowed to deduct up to 60% of their adjusted gross income for charitable donations of money to public charities.  However, the TCJA also doubled the standard deduction for federal income taxes, all but eliminating the incentive to itemize deductions and capitalize on the charitable deduction for many taxpayers.  The CARES Act, passed in the spring of 2020, includes a $300 above the line deduction for charitable contributions, and also increases the charitable deduction limit for donations of money to public charities (not including donor advised funds) to 100% of a taxpayer’s adjusted gross income for those who itemize.  These changes are only temporary and are scheduled to expire at the end of 2020.  It is yet to be seen whether a similar charitable deduction will be included in any future federal coronavirus relief packages.  If not, the postponement of the state income tax deduction for charitable contributions until 2022 means that Massachusetts taxpayers who postpone 2020 contributions until 2021 may lose a federal benefit with no offsetting state benefit. 

Upcoming Events at the BBA

By: Jennifer D. Taddeo, Conn Kavanaugh and Rebecca Tunney, Goulston & Storrs, Communications Committee, Trusts and Estates

Upcoming Programs at the BBA: 

Modifying Irrevocable Trusts: Decanting, Non-Judicial Settlement Agreements and other Trust Amendment Alternatives   Wednesday, January 6, 2021  This program will provide an introduction to various methods for modifying an irrevocable trust, including how and when to consider: (1) Modifications under the Massachusetts Uniform Trust Code, (2) reformations, (3) non-judicial settlement agreements, and (4) decanting.

Upcoming Events at the BBA – November 2020

By: Jennifer D. Taddeo, Conn Kavanaugh and Rebecca Tunney, Goulston & Storrs, Communications Committee, Trusts and Estates

Upcoming Programs at the BBA: 

Introduction to Revocable Trusts   11/4/2020 – 12:30PM to 1:30PM   This program will provide an introduction to revocable trusts in estate planning and review the key components of revocable trusts, including funding formulas, marital provisions, possible trust structures for children and other beneficiaries, and trustee provisions.  The program will also provide drafting suggestions and advice on avoiding certain pitfalls when advising clients about establishing revocable trusts.

Trust Situs: Planning and Administration Considerations   11/5/2020 – 2:00PM – 4:00PM  Trust situs can refer to taxation of a trust, jurisdictional matters, location of assets, and/or principal place of administration. What do trustees and estate planners need to know about this broad, sometimes confusing, topic? Please join us as our panel of experts discusses estate planning, trust administration, and fiduciary income tax considerations relating to trust situs.

Gifts and Sales to Intentionally Defective Grantor Trusts & Use of High Exemption Levels in 2020 – 2021  11/16/2020  – 12:30PM – 1:30PM   This seminar will provide an overview of the structure, tax treatment and proper administration of gifts and sales to intentionally defective grantor trusts (“IDGTs”). Some of the structuring topics we will discuss include:

  • proper trust drafting to ensure estate tax exclusion and grantor trust status for income tax purposes,
  • how to choose the right assets to transfer to an IDGT,
  • “entitizing” assets,
  • the proper documentation needed for a “gift” and/or “sale” of assets, including the use of “defined value” (Wandry) and “price adjustment” (King) language,
    timing issues,
  • debt v. equity issues,
  • ensuring sufficient cash flows,
  • the proper administration of the IDGT after the transfers, and
  • the presenters’ recent audit experience and the IRS’ hostility to the strategy.

We will also focus on the tax benefits including: (i) leveraging assets through use of value-freezing techniques and discounts, (ii) maximizing use of GST exemption, and (iii) optimal benefits of grantor trust status as a means to further deplete the grantor’s estate without consuming exemption and avoid income taxes upon the sale of assets and payments under any promissory note.

This seminar will further discuss why it may be critical to advise clients about using the enhanced wealth transfer tax exemptions now in light of possible post-election reforms. 

Estate Planning with Seniors during COVID-19: Undue Influence, Incapacity & best Practices  11/17/2020 – 12:30PM-1:30PM  In this second part of a two-part series focusing on the unique vulnerabilities of seniors during COVID-19, Attorneys Laura Goodman and Christina Vidoli will discuss best practices with respect to estate planning for seniors during the pandemic and, specifically, how to navigate new challenges such as virtual and socially distanced meetings without putting yourself at risk for later questions of undue influence or incapacity.

Evidence of Transferor’s Intent is Key in Distinguishing Loans and Gifts for Purposes of Calculating Estate Tax. Estate of Mary P. Bolles v. Commissioner, Tax Court Memo. 2020-71

By: Katelyn Allen, Nutter.


Throughout her life, the decedent made numerous transfers among her five children and kept a personal record of advancements and repayments to each child.  On the advice of tax counsel the decedent treated the advancements as loans and accounted for loan “forgiveness” each year for each child on the basis of the annual gift tax exemption.

From the year 1985 through 2007, the decedent transferred $1,063,333 to or for the benefit of her son Peter. Peter did not make any repayments to the decedent after 1988.  In 1989, the decedent executed a revocable trust, where she specifically excluded Peter from any distribution of her estate upon her death.

In 1996, the decedent executed an amendment to her revocable trust that included provisions for Peter and explicitly instructed the trustees to account for “loans” made to Peter during the decedent’s lifetime when calculating the share of assets Peter would receive upon the decedent’s death.  The decedent executed a contemporaneous document entitled “Acknowledgement and Agreement Regarding Loans”, in which Peter acknowledged that he received loans from the decedent and that the amount of the loans, including any accrued interest, would be taken into account for purposes of calculating his share of trust assets.

The decedent’s estate filed an estate tax return reporting the value of a Promissory Note and receivable due from Peter Bolles as zero and reporting no prior taxable gifts.


Upon audit of the decedent’s estate tax return, the Commissioner determined that the fair market value of the Promissory Note and receivable due from Peter was $1,063,333, and this amount was includable in the decedent’s estate under IRC Section 2033.  Alternatively, the Commissioner determined that if the fair market value of the Promissory Note and receivable was zero, as it had been reported on the estate tax return, the decedent had made $1,063,333 of taxable gifts to Peter during her lifetime, and that figure should be used in computing the estate tax liability under IRC Section 2001(b).

The Tax Court examined the traditional factors set forth in Miller v. Commissioner (Tax Court Memo. 1996-3, aff’d, 113 F.3d 1241 (9th Cir. 1997)) in determining whether the transfers from the decedent during her lifetime were loans or gifts.  The factors to be considered in making this determination are as follows:

  1. The existence of a promissory note or other evidence of indebtedness.
  2. If interest was charged.
  3. The existence of security or collateral.
  4. A fixed maturity date.
  5. Whether or not actual repayment or a demand for repayment was made.
  6. The transferee’s ability to repay.
  7. Records maintained by the transferor and/or transferee.
  8. The manner in which the transaction was reported for federal tax purposes.

The Court noted that the decedent recorded the advances to Peter as loans and accounted for interest, but there were no loan agreements, security on the loans, or attempts to demand repayment on the loans. The Court noted that the shift in 1989, when the decedent executed a trust agreement that blocked Peter’s receipt of assets at the time of her death, characterized a shift from “loans” to gifts.


The Court concluded the transfers to Peter from 1985 through 1989 were loans, but the transfers made from 1990 through 2007 were gifts.  The decedent shifted from extending and accounting for the transfers as loans to accounting for the transfers as advances against Peter’s share of the estate, as evidenced by her excluding Peter from his share of the inheritance in her 1989 trust.  As a result, the transfers from 1990 through 2007 were accounted as prior taxable gifts for purposes of calculating the estate tax due.

Advice for Planners:

When advising clients who wish to make transfers to family members, it is important to have the client clearly articulate his or her intentions – whether he or she wishes to make the transfer as a gift or whether he or she intends the transfer to be a loan with an expectation for repayment.  Once the client has articulated his or her intentions, it is important for the planner to craft proper evidence of the transfer as a loan or a gift and ensure that the client’s estate plan does not contradict his or her intentions. The planner should review the factors of Miller v. Commissioner to ensure the evidence of a loan or gift would be accepted or supported by the Commissioner and the Tax Court.

Tax Deadlines Extended Due to COVID-19

By: Justin M. Hannan and Gene Schlack, Day Pitney LLP.

To provide relief to taxpayers impacted by the COVID-19 pandemic, the IRS and the Massachusetts Department of Revenue have issued guidance in recent weeks extending the deadlines for filing and paying certain taxes.

Pursuant to IRS Notice 2020-18, Notice 2020-20, and Notice 2020-23, the filing deadlines for all federal income tax returns, gift tax returns and estate tax returns that would have been due between April 1 and July 15 have been automatically extended to July 15.  Additionally, any income tax payments and gift, estate and GST tax payments, including estimated quarterly payments, that were due between April 1 and July 15 are now due on July 15, and such payments made by the July 15 deadline will not incur interest or penalties.  There is no limit on the amount of tax payments that may be deferred. 

It is important to note that while these extensions apply to all taxpayers, including trusts and estates, they do not apply to tax returns and tax payments originally due prior to April 1.  For example, a trust that failed to file Form 1041 by March 15 is not saved by this guidance, and any taxes due with said Form 1041 would remain subject to penalties and interest.

Notably, IRS Notice 2020-23 clarifies that the extension to file tax returns also extends the deadline to file certain information returns, such as Form 3520, that are filed as attachments to such tax returns. This key point was previously unclear, creating substantial uncertainty among tax professionals.

In addition to the federal extensions, the Massachusetts Department of Revenue also extended various Massachusetts filing and payment deadlines. Per Technical Information Release (TIR) 20-4, state filings and payments for personal income tax, estate and trust income tax, and income tax due with a partnership composite return with an April 15, 2020 due date have been automatically extended to July 15.  Similarly, installments for estimated income tax payments that would otherwise be due on April 15 and June 15 are now due on July 15.  The filing and payment deadlines for Massachusetts estate tax returns have not been extended.

Though TIR 20-4 does not extend corporate excise tax filings and payments, it does waive late-file and late-pay penalties (but not interest) for corporate excise returns and payments with original due dates of April 15 that are filed and paid by July 15. 

Massachusetts (Temporarily!) Allows Remote Notarization

Massachusetts (Temporarily!) Allows Remote Notarization

The BBA endorsed temporary legislation authorizing notarization and witnessing of documents to be conducted remotely, by videoconference.  The Legislature passed, and the Governor enacted, such a law, which addresses an urgent need that was brought to our attention by practitioners from a number of our sections, including Trusts & Estates and Real Estate.  Read an exclusive Boston Bar Journal article on the requirements and restrictions for this new law.  Thank you to the authors Sara Goldman Curley, Kerry Spindler, and Rebecca Tunney.

New Standing Orders Extend Court Closures and Toll Probate Court Deadlines During COVID-19

By: Ann Hetherwick Cahill of Burns & Levinson LLP and Darian M. Butcher of Day Pitney LLP, Co-Chairs of the BBA Trusts & Estates Probate Litigation Committee

The Supreme Judicial Court and the Probate and Family Court each issued new Standing Orders that went into effect May 4, which supersede the prior Standing Orders.  It is important to read both new Standing Orders together: the SJC Standing Order is available here and the Probate and Family Court Standing Order is available here

Pursuant to the SJC Standing Order, until at least June 1, the courthouses will remain closed to the general public, except to address emergency matters that cannot be resolved through remote methods, such as telephone, video conference, e-mail, and comparable means.  The Probate and Family Court Standing Order enumerates 10 categories of emergency matters, which include, among other things, petitions and motions concerning medical treatments, petitions for appointment of a temporary guardian or conservator, and petitions and motions for appointment of special personal representatives. 

Regarding non-emergency matters, the SJC Standing Order directs the Trial Court departments to identify the categories of non-emergency matters that each will attempt to address virtually.  In its Standing Order, the Probate and Family Court has identified a goal of hearing as many case types and events as possible.  Accordingly, beginning on May 11, 2020, the Probate and Family Court will attempt to hear virtually all case types and events, except for trials and evidentiary hearings, where it is practicable to do so.  Determinations concerning the volume of cases to be heard and the case types will be made by the Register and First Justice and will differ across divisions of the Probate and Family Court. 

The Standing Orders also affect deadlines in the Probate and Family Court that fall between March 16 and June 1 in the following ways:

1. Most Deadlines are Tolled until a Date after June 1:  The deadline extensions of Paragraph 12 of the SJC Order control with the exception of five enumerated types of deadlines listed below.  Thus, in most instances, Paragraph 12 of the SJC Standing Order extends all deadlines (based on “statutes, court rules, standing orders, tracking orders, or guidelines”) that expire between March 16 and June 1. 

The new deadline is calculated by determining the number of days remaining after March 16 until the original deadline, and add that number of days after June 1.  For example, if the original deadline was March 20, then 4 days remained as of March 16, so the new deadline would be June 5 (June 1 plus 4 days). 

The new deadline calculations also apply to deadlines that would have originated during the pandemic. For example, if you served discovery while working from home during this pandemic, Paragraph 12 of the SJC Order directs that your new deadline only begins to run as of June 1.       

2. The Five Exceptions – These Deadlines Are Not Tolled:  Under Paragraph H of the Probate and Family Court Standing Order, the above tolling does not apply to the following five types of deadlines:

i. Findings required by G. L. c. 208, § 1A;
ii. Objection period in G. L. c. 208, § 21, so that judgments absolute may enter in divorce cases; 
iii. Time period to file an answer or any other responsive pleading to a contempt summons; 
iv. Time period to file an appearance or affidavit of objections pursuant to G. L. c. 190B, § 1-401; and 
v. Time period to request a motion for a new trial or to amend findings and/or judgments in Rule 59. 

Thus, for cases involving these five types of deadlines with expiration dates falling between March 16 and June 1, the deadlines are not extended.  This is a trap for the unwary as failure to take heed of these exceptions could result in a defendant being defaulted if they failed to file an answer or responsive pleading to a contempt summons, or a respondent could lose the opportunity to appear and file an affidavit of objections. 

The new Standing Orders also address the operations of the Clerks’, Registers’, and Recorder’s Offices, all of which continue to conduct court business for emergency matters and non-emergency matters as designated by their respective court department.  Specifically, the Probate and Family Courts are accepting new matters for filing by mail, e-mail, or e-filing were available, unless filings in emergency matters cannot be accomplished electronically.

For other details about trials and extensions of Probate and Family Court orders, including for treatment plans and temporary orders of appointment in guardianship and conservatorship cases, please review the SJC Standing Order (here) and the Probate and Family Court Standing Order (here).