When a New York Exempt Resident Trust Meets the Sale of a Business

November 12, 2019

Imagine, if you will, the owner of a closely held business. Although the business has done well, the owner believes they can take it to the proverbial “next level” by dedicating another five years of intense effort and some additional investment, following which they will try to sell the business.

After learning of this “plan” during one of their regular meetings,[i] the owner’s attorney and accountant recommend, among things, that the owner consider the creation of a trust for the benefit of the owner’s family. They explain that the trust could be funded with an interest in the business.

The owner asks . . .

Why A Trust?

Many people are aware that trusts are often used as vehicles through which the owner of a closely held business may pass along to, or for the benefit of, their family – either during the owner’s life[ii] or upon their death[iii] – a beneficial, or economic, interest in the business without actually giving them direct, or legal, ownership in the business.

An owner may have several reasons for employing a trust, rather an outright transfer, to pass along the business, and the value it represents, to their spouse or children. For example, where a child is the issue of the owner from a prior marriage, the owner may want to provide for their current spouse while also ensuring that the child will receive their share of the remainder of the trust upon the death of the second spouse.[iv] Or the owner may be interested in setting aside assets to provide for the well-being of the child while preventing the child’s creditors (present or future)[v] from reaching such assets. Then there are those owners who (at least in their parental roles) are control freaks, and for whom death is not the end insofar as their ability to control their wealth is concerned. Oh well.[vi]

Funding the Trust

Ideally, a trust will be funded with an asset that is reasonably expected to appreciate significantly in value. The owner of a closely held business will typically transfer an equity, often non-voting, interest in the business by either gifting or selling[vii] the interest to the trust.[viii] In general, an owner-grantor will try not to incur a gift tax liability on an inter vivos transfer; rather, they will seek to maximize the use of all or a portion of their remaining exemption amount.[ix]

The trustee will hold the equity interest and, in accordance with the terms of the trust agreement – which reflect the owner-grantor’s directions or preferences – the trustee may distribute the trust’s income, and perhaps its corpus, among the one or more beneficiaries of the trust.[x]

The owner does not retain any interest in or control over the trust. This helps to ensure that the transfer to the trust is “completed” for gift tax purposes,[xi] and prevents the value of the trust from being included in the grantor’s gross estate for purposes of the estate tax. In this way, the business interest that was transferred to the trust,[xii] along with the post-transfer income generated by the interest, as well as its appreciation in value, are excluded from the grantor’s estate.

Income Tax

A lot of planning goes into the transfer of equity in a business to trust. Unfortunately, there is one important trait of the trust is often overlooked: its treatment for purposes of the income tax; specifically, the fact that a trust is itself a taxpayer, unless it is a grantor trust.[xiii]

Non-Grantor Trust

This is no small matter when one considers that non-grantor trusts are generally subject to the same graduated federal income tax rates as individuals, except that the highest rates[xiv] apply at a much lower level of taxable income in the case of a trust than for an individual; the rate brackets are much more compressed, with the result that a trust will generally pay more federal income tax than an individual on the same amount of taxable income.[xv] The same holds true for the federal surtax on net investment income.[xvi]

However, a non-grantor trust may not have to pay federal income tax for a taxable year if it distributes its taxable income for such year (with certain modifications)[xvii] to its beneficiaries on a current basis. The trust is allowed to claim a deduction in respect of the distribution for purposes of determining its taxable income for the year.[xviii] In turn, the distribution “carries out” the trust’s income into the hands of the recipient beneficiaries,[xix] thereby shifting the liability for the distributed income to the beneficiaries.[xx]

In this way, the non-grantor trust’s income is taxed only once: to the trust to the extent it does not distribute its income, or to the trust’s beneficiaries to the extent such income is distributed by the trust.[xxi] Income that has already been taxed to the trust in a prior year is not taxed again when it is distributed to the beneficiary.

Grantor Trust

That being said, there is a special set of rules that causes the taxable income and gains of a trust to be taxed, neither to the trust nor to its beneficiaries, but to the grantor of the trust.

Under the “grantor trust” rules,[xxii] the individual grantor – i.e., the business owner, for our purposes – who contributes property (equity in the business) to the trust will be treated as the owner of the trust property, and of the income and gains from such property, if they retain certain rights with respect to the property.[xxiii] Thus, the grantor must include the trust’s income and gains on their individual income tax return, and pay the tax thereon.[xxiv]

This allows the trust to grow without being reduced by tax payments, and it further reduces the grantor’s gross estate by causing the grantor to use their other assets to satisfy the income tax liability.[xxv]

New York Taxation of Trusts

For the most part, N.Y. follows the federal rules as to the income taxation of trusts. In applying these rules, however, along with some uniquely N.Y. modifications thereto, the State divides trusts into resident and non-resident trusts, and then into grantor[xxvi] and non-grantor trusts.

In general, a non-grantor trust will be treated as a N.Y. resident trust if it consists of property:

  • that was transferred by the will of a decedent who, at the time of such decedent’s death, was domiciled in N.Y.;
  • of a person who was domiciled in N.Y. at the time such property was transferred to the trust, if such trust was then irrevocable; or
  • of a person domiciled in N.Y. at the time such trust became irrevocable, if it was revocable when such property was transferred to the trust, but has subsequently become irrevocable.[xxvii]

Note that the residence of the trustee does not affect the status of a trust as resident or nonresident.

A trust that is not a resident trust, as defined by these rules, is treated as a nonresident trust for purposes of the N.Y. income tax.[xxviii]

The N.Y. taxable income of a resident trust is its federal taxable income for the tax year, subject to certain modifications. The resident trust is subject to tax on its N.Y. taxable income at the rates applicable to individual taxpayers.[xxix]

A nonresident trust is subject to N.Y. income tax only as to its N.Y. source income.[xxx] Thus, income and gain attributable to the trust’s ownership of any interest in real or tangible personal property in N.Y. is taxable.[xxxi] It also includes the trust’s distributive share of partnership income that is sourced in N.Y., as well as the trust’s pro rata share of S corporation income sourced in N.Y., including income or gain attributable a trade or business carried on in the State.[xxxii]

An “Exempt” Resident Trust?

There is, however, an exemption from N.Y. income tax for a resident trust that is not a grantor trust and that meets the following requirements:

  • the trustee is not domiciled in N.Y.;[xxxiii]
  • the trust has no N.Y. assets;
    • intangible assets, like stock of a corporation, are deemed sitused at the domicile of the nonresident trustee, outside N.Y.;[xxxiv]
    • if the trust has any tangible assets located in N.Y. (e.g., real estate), the trust will remain subject to N.Y. tax; and
  • the trust does not have any N.Y.-source income or gain; this includes, for example, flow-through income from a partnership or S corporation; any N.Y. income will cause the trust to be taxable in N.Y.[xxxv]

A N.Y. resident trust that satisfies these conditions will not be subject to N.Y. income tax.[xxxvi]

If the exempt resident trust were to make a current distribution to a N.Y. beneficiary – whether mandatory or discretionary – an amount up to the trust’s taxable income for that tax year would be included in the beneficiary’s federal adjusted gross income for the year and, thereby, in their N.Y. adjusted gross income for that year.[xxxvii] Thus, the income would be subject to N.Y. income tax in the hands of the beneficiary.

However, if the trust does not make current distributions to its N.Y. beneficiaries, the trust’s income for the tax year will not be subject to N.Y. income tax either in the hands of the trust or of its beneficiaries, though the trust will, of course, be subject to federal income tax with respect to such undistributed income.

The “Throwback” – Sort Of

This raises the following question: what happens when an exempt resident trust distributes to its N.Y. beneficiaries income that the trust accumulated in earlier tax years, on which the trust paid federal income tax, but no N.Y. income tax?

Before January 1, 2014, because such a distribution of prior year income would not have been included in a N.Y. beneficiary’s federal adjusted gross income for the year received, it would not have been subject to N.Y. income tax.

Beginning after 2013, however, a N.Y. resident beneficiary of an exempt resident trust must include in their N.Y. adjusted gross income any income that was accumulated by the trust in a tax year beginning on or after January 1, 2014 and that is distributed to a beneficiary of the trust in a year subsequent to the year in which the trust included the income on its federal tax return (an “accumulation distribution”).[xxxviii]

In order to facilitate the enforcement of this rule, N.Y. requires an exempt resident trust to submit Form IT-205-C, “New York State Resident Trust Nontaxable Certification” every year with its Fiduciary Income Tax Return (on Form IT-205).[xxxix]

When an exempt resident trust makes an accumulation distribution for a tax year to a beneficiary who is a New York State resident, the trust must report the distribution on Form IT-205-J, “New York State Accumulation Distribution for Exempt Resident Trusts,” which is filed with its Form IT-205 for that year.

According to the Form IT-205-J instructions, an accumulation distribution is the excess of the amounts properly paid, credited, or required to be distributed during the tax year of the distribution (other than income required to be distributed currently), over the trust’s DNI reduced by income required to be distributed currently. To have an accumulation distribution, the distribution must exceed the accounting income of the trust.

In general, a resident beneficiary receiving an accumulation distribution from an exempt resident trust must include the accumulation distribution in their N.Y. adjusted gross income for the year of the distribution.[xl]

Significantly, when one works through the federal “throwback” provisions, which are incorporated by reference into the N.Y. rule,[xli] it appears that capital gains that are not distributed during the year[xlii] in which they are recognized by the trust for federal tax purposes may not be subject to the N.Y. accumulation regime when distributed in a later year. That’s because capital gain is generally not included in DNI.[xliii] In other words, capital gain attributable to an earlier tax year may escape N.Y. tax when distributed by an exempt resident trust in a later year to the trust’s N.Y. resident beneficiaries.

The Sale

Returning to our owner, let’s assume they and their family are N.Y. residents, and that the business operates in N.Y. The business is organized as a C corporation,[xliv] and doesn’t own any N.Y. real property.[xlv]

The owner creates and funds a non-grantor trust with non-voting shares of the C corporation’s stock, and nothing else.[xlvi] The trust is a N.Y. resident trust.[xlvii] The trustee, is not a N.Y. resident and, so, the shares of stock are not treated as N.Y. property.

The trust agreement authorizes the trustee to distribute among any or all of the beneficiaries so much of the trust income and/or principal, and at such times, as the trustee determines in their sole discretion.

A few years pass, the value of the business increases, the owner begins to solicit and entertain bids for the sale of the business.[xlviii] A few months into the process, the business is sold – miracle of miracles, a sale of stock.[xlix]

The owner and the trust report the gain from the sale on their respective federal tax returns.[l] The owner also reports the gain on their N.Y. tax return and pays the resulting tax.[li]

The trust is an exempt resident trust. Therefore, it is not subject to N.Y. income tax on the gain from the sale of the stock.

The trustee invests the proceeds, earning dividends and interest. The trust does not make any distributions. It pays federal taxes on such income.

Several years later, in accordance with its terms, the trust terminates and distributes all of its principal and undistributed income to the beneficiaries, all of whom still reside in N.Y.

Although the trust’s previously undistributed income will be subject to N.Y. income tax in the hands of the recipient beneficiaries, the capital gain should not be.[lii]


[i] Would that it were so. Many issues could be addressed before developing into more difficult, more expensive issues.

[ii] An inter vivos transfer, or gift, of an interest in the business or in real property associated with the business.

[iii] A testamentary transfer: a devise in the case of real property, and a bequest of an interest in the business.

[iv] Indeed, this is the premise underlying the estate tax marital deduction afforded the so-called “QTIP” trust. IRC Sec. 2056(b)(7).

[v] The child’s future spouse – as yet unidentified – if often seen as the main culprit.

[vi] N.B.: The owner-grantor should not serve as trustee of the trust if one of their goals is to remove the trust from their gross estate for purposes of the estate tax. For that reason, it would behoove the owner to prepare a shareholders’ agreement, to be entered into with the trustees, which would, among other things, give the owner the right to drag-along the other equity owners in the event the owner decides to dispose of the business.

[vii] The sale will typically be to a so-called “grantor trust,” which is a trust the property of which the grantor is treated as still owning. Because a taxpayer cannot “sell” property to themselves (except, perhaps, in a metaphysical sense), the transfer is not treated as a taxable event. See, e.g., Rev. Rul. 85-13. This principle provides the basis for a transaction that you may have heard about: the sale to an “intentionally defective grantor trust” (the word “defective” is so far off the mark).

[viii] You’ll note that the owner is not, thereby, “retaining” the right to vote the gifted shares – these shares have no right to vote. IRC Sec. 2036. In the case of a corporation, all it takes is a simple recapitalization; an “E” reorganization under Reg. Sec. 368(a)(1)(E).

[ix] IRS Sec. 2010 and Sec. 2505. The fact that the property being transferred represents a non-voting, non-readily tradeable, equity interest in a closely held business, will typically enable the grantor to leverage their exemption amount. Of course, any portion of their exemption amount that remains at the owner’s death may be used to cover a testamentary transfer. In most cases, the IRS will, almost as a matter of course, challenge the valuation of the business. Many taxpayers utilize a formula clause, based on the Tax Court’s decision in Wandry, to address the risk that such a challenge may convert an otherwise non-taxable gift into a taxable transfer. T.C. Memo. 2012-88.

[x] There are so many formulations. For example, the trust agreement may authorize the trustee to distribute so much of the income or principal of the trust, at such times and in such amounts, as the trustee, in the exercise of their sole discretion determines; it may direct that all income be distributed at least currently, and authorize the trustee to distribute any part of the principal that the trustee determines necessary for the health, education, maintenance and support of the beneficiary. In each case, the advisor’s responsibility is to see that the grantor act reasonably in light of the property being transferred, its likely future, the unique traits of each known beneficiary, and the advisor’s own experience – this last is where some aspect of the “social sciences” come into play.

[xi] A very important consideration if the goal is to remove the business interest, and its future appreciation in value (yes, that’s redundant), from the grantor’s estate. Reg. Sec. 25.2511-2.

[xii] Hopefully, without triggering any gift tax liability.

[xiii] IRC Sec. 1(e).

[xiv] 37-percent as to ordinary income, and 20-percent as to qualified dividends and capital gain. IRC Sec. 1(a) and Sec. 1(h).

[xv] In 2019, for example, the top federal rate of 37-percent for ordinary income applies to the taxable income of a married couple filing jointly when their taxable income exceeds $612,350, whereas the same rate applies to a trust when its taxable income exceeds $12,750. In the case of capital gains, the top federal rate of 20% will apply to a married couple filing jointly with taxable income exceeding $488,850; for a trust, the threshold is $12,950.

[xvi] IRC Sec. 1411. Married individuals filing jointly are subject to the tax when their “modified adjusted gross income” exceeds $250,000; trusts when it exceeds $12,500. https://www.taxlawforchb.com/2014/07/s-corp-trusts-the-3-8-surtax-on-nii-part-iv/

[xvii] Its distributable net income, or DNI. IRC Sec. 643.

[xviii] A distribution deduction.

[xix] And preserves its character in the hands of the beneficiaries. See, e.g., IRC Sec. 662(c).

[xx] The deduction by the trust is under IRC Sec. 651 and Sec. 661; the inclusion by the beneficiaries is under IRC Sec. 652 and Sec. 662.

In recognition of the fact that a trust may not be able to determine its DNI for a tax year before the end of such year, the trust is allowed to claim a distribution deduction for the year for distributions made to its beneficiaries during the first 65 days of the immediately succeeding year. IRC Sec. 663(b).

[xxi] This is in contrast to a pass-through business entity, such as a partnership/LLC or an S corporation, the “taxable income” of which flows through and is currently taxed to the partners/members and shareholders, without regard to whether it has been distributed to them. IRC Sec. 702 and Sec. 1366. The partnership and the S corporation are not, themselves, taxable entities (at least in most cases). IRC Sec. 701 and Sec. 1363(a), respectively.

[xxii] IRC Sec. 671 through Sec. 679.

[xxiii] These rights need not be of a kind that would cause the trust property to be included in the grantor’s gross estate. For example, the grantor’s right to reacquire the contributed property from the trust in exchange for property of equivalent value will cause the trust to be treated as a grantor trust without exposing the trust property to inclusion in the grantor’s estate. IRC Sec. 675(4). In addition, the right to borrow from the trust without adequate security will result in grantor trust treatment, without inclusion in the estate (provided there is adequate interest charged). IRC Sec. 675(2).

It is this disconnect between the estate and income tax rules that facilitates some very effective estate tax planning strategies. It is also this disconnect that the Obama administration tried to eliminate year after year, without success. Just look at the administration’s Green Books.

[xxiv] IRC Sec. 671.

[xxv] This assumes the grantor has enough liquidity from other sources with which to pay the income tax liability. The grantor may waive or release their rights under the trust agreement, thereby “converting” the trust to a non-grantor trust.

[xxvi] If the individual who is treated as the grantor-owner of the trust is a N.Y. resident, the income and gains of the trust will be taxed to them accordingly. NY Tax Law Sec. 601(a). Likewise in the case of a nonresident grantor-owner. NY Tax Law 601(e).

[xxvii] NY Tax Law Sec. 605(b)(3).

For purposes of these rules, a trust is revocable if it is subject to a power, exercisable immediately or at any future time, to revest title in the person whose property constitutes such trust, and a trust becomes irrevocable when the possibility that such power may be exercised has been terminated.

[xxviii] NY Tax Law Sec. 605(b)(4).

[xxix] NY Tax Law Sec. 618 and Sec. 601(c).

[xxx] NY Tax Law Sec. 631 and Sec. 633.

[xxxi] NY Tax Law Sec. 631. In general, an interest in real property includes an interest in a partnership/LLC, S corporation, or non-publicly traded C corporation with no more than 100 shareholders, that owns real property located in N.Y, provided the fair market value of such real property represents at least 50-percent of the value of all of the entity’s assets, excluding those assets that the entity has owned for less than two years.

[xxxii] NY Tax Law Sec. 631 and Sec. 632.

[xxxiii] This is often accomplished by appointing a Delaware corporate trustee – there is no Delaware income tax on a trust that accumulates income for beneficiaries who are not residents of Delaware.

[xxxiv] NY Tax Law Sec. 605(b)(3)(D)(ii).

[xxxv] NY Tax Law Sec. 631(b)(1). See also TSB-M-18(1)I.

[xxxvi] NY Tax Law Sec. 605(b)(3)(D)(i).

[xxxvii] IRC Sec. 662; NY Tax Law Sc. 612.

[xxxviii] NY Tax Law Sec. 612(b)(40).

[xxxix] In general, the due date is April 15 of the succeeding year. There is a failure to file penalty.

[xl] NY Tax Law Sec. 612(b)(40). There are exceptions: where the accumulation distribution is attributable to a tax year that the trust was subject to N.Y. tax, or a tax year starting before January 1, 2014; where the accumulation distribution is attributable to a tax year prior to when the beneficiary first became a N.Y. resident, or a tax year before the beneficiary was born or reached age 21; or where the income was already included in the beneficiary’s gross income. See also TSB-M-14(6)S.

[xli] IRC Sec. 667(a), the first sentence, which in turn refers to IRC Sec. 666; these sections refer to IRC Sec. 662(a)(2) and Sec. 661(a)(2).

[xlii] As “other amounts properly paid . . .” See IRC Sec. 661(a)(2) and Sec. 662(a)(2) – both of which are limited by DNI.

[xliii] IRC Sec. 643(a)(3).

[xliv] Otherwise, we have to deal with the flow through of N.Y-source income of a partnership or S corporation.

[xlv] In my world, the real property is held by the owner in an LLC that leases the property to the corporation.

[xlvi] Let’s assume the owner did not incur any gift tax liability on the transfer.

[xlvii] In addition, the trustee is “independent” of the owner within the meaning of the grantor trust rules. See IRC Sec. 674.

[xlviii] Although our assumed facts do not raise the issue, the owner has to be careful about a sale that follows on the heels of a gift. First, the sale may fix the fair market value of the gifted shares notwithstanding what the owner’s appraisal concludes. Second, if negotiations for the sale preceded the gift transfer, the owner may be charged with the gain from the sale under assignment of income principles.

[xlix] Buyers will generally prefer to acquire the target’s assets: they receive a basis step-up and they cherry pick the liabilities to be assumed. I just didn’t want to deal with a liquidating distribution following an asset sale.

[l] Forms 1040 and 1041, respectively. Long term capital gain: 20% tax on the gain, and the 3.8% surtax on net investment income. IRC Sec. 1(h) and Sec. 1411, respectively.

[li] 8.82% personal income tax. The owner does not reside in N.Y. City (which imposes a 3.876% tax on its residents).

[lii] Of course, to the extent the distribution carries out current DNI, the beneficiaries will be taxed thereon by both the IRS and N.Y.