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1 Boston Brussels Chicago Düsseldorf Frankfurt Houston London Los Angeles Miami Milan Munich New York Orange County Paris Rome Seoul Silicon Valley Washington, D.C. Strategic alliance with MWE China Law Offices (Shanghai) © McDermott Will & Emery. The following legal entities are collectively referred to as "McDermott Will & Emery," "McDermott" or "the Firm": McDermott Will & Emery LLP, McDermott Will & Emery AARPI, McDermott Will & Emery Belgium LLP, McDermott Will & Emery Rechtsanwälte Steuerberater LLP, McDermott Will & Emery Studio Legale Associato and McDermott Will & Emery UK LLP. These entities coordinate their activities through service agreements. This communication may be considered attorney advertising. Previous results are not a guarantee of future outcome. What Fiduciaries and Their Advisors Need to Know About Navigating the 3.8% Net Investment Income Tax under Code Section 1411 Presented to the Chicago Estate Planning Council on December 10, 2014 By Richard L. Dees McDermott Will & Emery LLP Chicago Illinois

2 What is in the Final and Reproposed Regulations?  General Rules  Specific Rules Applicable to Individuals  Specific Rules Applicable to Estates and Trusts  Definition of Net Investment Income  Trades or Businesses Subject to Tax: Passive Activities, Financial Instruments/Commodities Trading  Income on Working Capital  Dispositions of Partnerships and S corporations (Reproposed)  Exception for Qualified Plan Distributions  Exception for Self-Employment Income  CFC and PFIC rules  Effective Date and Transition Rules 2www.mwe.com

3 Net Investment Income Tax: General Rules  For an individual, 3.8% tax on the lesser of (a) an individual’s net investment income (“NII”) or (b) the excess of the individual’s modified adjusted gross income (“MAGI”)* over certain thresholds (not indexed for inflation): – $250,000 in the case of a joint return or surviving spouse, – $125,000 in the case of a married individual filing a separate return, or – $200,000 in any other case *Only modification to AGI relates to foreign earned income for an individual living abroad. 3www.mwe.com

4  Net Investment Income is the excess (if any) of – the sum of (i) Gross Income from (a) interest, (b) dividends, (c) annuities, (d) royalties, and (e) rents (collectively “Specified Income”), other than Specified Income derived in the ordinary course of a trade or business that is not a “Covered trade or business”, (ii) Other gross income derived from a “Covered trade or business”, and (iii) Net gain attributable to the disposition of property other than property held in a trade or business that is not a “Covered trade or business” (“Includable Net Gain”), over – the deductions allowed by Code Sections 1 through 1563 (subtitle A) that are properly allocable to this gross income or net gain. Net Investment Income Tax: General Rules 4www.mwe.com

5  Note that there is no look-through rule for dividends from a subsidiary engaged in the same trade or business.  Compare Code Section 1362(d)(3)(c)(iv) (referenced by Code Section 1375(b)(3)): – If an S corporation holds stock in a C corporation meeting the requirements of section 1504(a)(2), the term “passive investment income” shall not include dividends from such C corporation to the extent such dividends are attributable to the earnings and profits of such C corporation derived from the active conduct of a trade or business. Net Investment Income Tax: General Rules 5www.mwe.com

6  A trade or business is a “Covered trade or business” if such trade or business is: – (i)a passive activity (within the meaning of Code Section 469) with respect to the taxpayer, or – (ii)a trade or business of trading in financial instruments or commodities (as defined in Code Section 475(e)(2)).  Proposed Regulations under Code Section 1411 provide that a passive activity is: – (i) an activity that is a trade or business (within the meaning of Code Section 162); and – (ii)such trade or business is a passive activity within the meaning of Code Section 469 and the regulations thereunder.  Below we discuss how to ACTIVATE business and rental income Net Investment Income Tax: General Rules 6www.mwe.com

7 Prop. Treas. Reg. § (a): Except as otherwise provided, all Internal Revenue Code provisions that apply for chapter 1 purposes in determining taxable income (as defined in section 63(a)) of a taxpayer also apply in determining the tax imposed by section Net Investment Income Tax: General Rules 7www.mwe.com

8  Timing: Unless provided otherwise, gain not recognized in a particular year under chapter 1 is not recognized for that year for purposes of Code Section 1411 – Code Section 453 (installment sales) – Code Section 1031 (like-kind exchanges) – Code Section 1033 (involuntary conversions) – Code Section 121 (sale of principal residence)  Deferral and disallowance provisions used in determining taxable income apply in determining NII – Code Section 163(d) (limitation on investment interest) – Code Section 265 (expenses and interest relating to tax-exempt income) – Code Section 465 (at risk limitations) – Code Section 469 (passive activity loss limitations) – Code Section 704(d) (partner loss limitation) – Code Section 1366 (S corporation shareholder loss limitations) – Code Section 1212 (capital loss carryover limitations) Net Investment Income Tax: General Rules 8www.mwe.com

9 Net Investment Income Tax: General Rules  Carryovers – Allowed for determining NII in the same year as allowed for taxable income – Carryovers can be utilized even if carried from a year that precedes the effective date of Code Section1411  No reduction to NII for net operating loss carry forwards 9www.mwe.com

10 Fiduciaries: Which trusts and estates are subject to the NII Tax?  Section 1411(a)(2) imposes a tax of 3.8% on the net investment income of trusts and estates above an income threshold – Treas. Reg. § provides special rules for applying section 1411 to estates and trusts, including an estate or trust with a short taxable year due to the formation or termination of the estate or trust (do not prorate the income threshold) or a change in accounting period (do prorate) – The preamble to the Final Regulations thoughtfully reexamines which trusts taxed under the income tax also should be subject to the NII Tax, including – Pooled Income Funds (yes) Cemetery Perpetual Care Funds (No) and Qualified Funeral Trusts (practically No) Alaska Native Settlement Trusts (No) 10www.mwe.com

11 Fiduciaries: What are the specifically excluded trusts? – In addition, Treas. Reg. § (b) specifically excludes the following fiduciary arrangements from the NII Tax: Estates or Trusts set up for wholly charitable purposes as defined in section 170(c)(2)(B) Trusts exempt from tax under section 501(a) A charitable remainder trust ("CRT") under section 664, but distributions to beneficiaries may be taxable Any other trust, fund, or account that is exempt from taxes under sections 641 – 646 (i.e., health savings accounts, 529 plans, Archer medical savings accounts, Coverdell education savings accounts) Foreign Estates and Trusts with no U.S. beneficiaries – The preamble indicates that section 1411 does not apply to business trusts at the entity level, common trust funds and designated settlement funds 11www.mwe.com

12 Fiduciaries: Are Grantor Trusts treated as individuals or trusts?  A trust (or any portion of a trust) deemed owned by its grantor (creator) or other person (usually a holder of an unrestricted power of withdrawal) for fiduciary income tax purposes is disregarded for purposes of the NII Tax  Therefore, each item of income or deduction attributable to the grantor trust (or portion thereof) is treated as if it had been received by, or paid directly to, the grantor or other deemed owner for purposes of calculating such person's net investment income  The cause for grantor trust status is irrelevant and can result from: – "Defective" grantor trust – Power of withdrawal – QSST as to K-1 income 12www.mwe.com

13 Fiduciaries: What about Charitable Remainder Trusts?  CRTs are not subject to the NII Tax  However, annuity and unitrust payments to non-charitable beneficiaries are deemed to consist of NII equal to the lesser of: – The total amount of the distribution or – The sum of the current and accumulated NII  Accumulated NII is – The total amount of post 12/31/12 NII Less – The amount of NII distributed in all taxable years post 12/31/12  The final regulations provide a more complicated scheme for taxing distributions from a CRT demanded by taxpayers’ advisors (NII Tax included in income tax rate for “worst out first” rules) 13www.mwe.com

14 Fiduciaries: How is AGI determined for the NII Tax? AGI for a trust or estate is same as an individual, except that IRC §67(e) adds three deductions that apply only to trusts and estates:  Administration expenses unique to the fiduciary arrangement – Other administration expenses are miscellaneous itemized deductions  Distributions to the beneficiaries limited to distributable net income ("DNI")  The fiduciary's "personal exemption" – $600 exemption for an estate – $300 for a simple trust (a trust distributing all its fiduciary accounting income) – $100 for a complex trust; except the $300 exemption applies if the trust is a simple trust taxed as a complex trust due to distributions in excess of fiduciary accounting income 14www.mwe.com

15 Fiduciaries: How is undistributed net income computed? For an estate or trust, the 3.8% NII Tax is imposed on the lesser of: – Undistributed Net Investment Income ("UNII") or – The excess of AGI over the threshold amount The threshold amount for 2014 is $12,150 (income level at which 39.6% rate applies) is adjusted for inflation The Regulations compute UNII using existing fiduciary income tax concepts in Subchapter J UNII is determined by reducing the total NII by – Distributed NII and – Charitable deductions taken into account under IRC § 642(c) Distributed NII is the lesser of: – The distribution deduction under IRC § 651 or IRC § 661 or – The NII of the estate or trust 15www.mwe.com

16 Fiduciaries: How is the charitable “deduction“ computed?  IRC § 642(c) reduces fiduciary gross income paid to a charity (or permanently set aside by an estate for charity)  Items of income are allocated to charity, rather than deducted  IRC § 642(c) reduces undistributed NII, but not AGI  All items of gross income must be included in the distribution pro rata unless allocation has economic significance  Compare with individual charitable deduction that reduces neither AGI nor NII 16www.mwe.com

17 Fiduciaries: How does DNI affect the NII Tax computation? DNI is taxable income (as defined in IRC § 63) of the estate or trust reduced by items in Treas. Reg. § 1.643(a)-2 through 1.643(a)-7: – Personal exemption – Capital gains and losses allocable to fiduciary accounting principal – Extraordinary dividends and taxable stock dividends allocable to principal – Tax-exempt income – Income of a foreign trust – Exclusion for dividends (repealed in 1986) Treas. Reg. § fixes a flaw in the proposed regulations in the computation of DNI The definition of DNI encourages distributions when beneficiaries are middle or lower income, pressuring trustees 17www.mwe.com

18 Tax Rates for Trusts and Single Individuals Assuming Investment Income AGIORD INCOMECAP GAINSORD INCOMECAP GAINS SINGLE INDIVIDUAL TAXPAYERCOMPLEX TRUST TAXPAYER $ -0.00% $100 exempt 15.00%-33.00% 20.00% $ 10, %0.00% 33.00%20.00% $ 12, %0.00% 43.40%23.80% $ 18, %0.00% 43.40%23.80% $ 46, %15.00% 43.40%23.80% $ 97, %15.00% 43.40%23.80% $ 193, %15.00% 43.40%23.80% $ 200, %18.80% 43.40%23.80% $ 372, %18.80% 43.40%23.80% $ 408, %18.80% 43.40%23.80% $ 410, %23.80% 43.40%23.80% 18www.mwe.com

19 Fiduciaries: Can (should) capital gains be included in DNI? Adding capital gains to accounting income with a mandatory income trust will usually be contrary to grantor's intent Treas. Reg. § 1.643(a)-3 provides three situations for allocating capital gains to DNI: – Allocated to income by trust or state law due to a unitrust payout or power to adjust – If consistently treated as part of distributions to beneficiaries from inception (The final regulations deny trustees a fresh start election) – Actually distributed or considered by the fiduciary in determining distributions Partnership distributions of accounting income including capital gains, if instrument or state law provides (Crisp v. US); consider effect of ownership of entire entity by trust 19www.mwe.com

20 Redline between proposed and final regulations for capital gain inclusion: consistency required? (b)Capital gains included in distributable net income. Gains from the sale or exchange of capital assets are included in distributable net income to the extent they are, pursuant to the terms of the governing instrument and applicable local law, or pursuant to a reasonable and consistentimpartial exercise of discretion by the fiduciary (in accordance with a power granted to the fiduciary by applicable local law or by the governing instrument, if not inconsistent withprohibited by applicable local law)- (1) Allocated to income (but if income under the state statute is defined as, or consists of, a unitrust amount, a discretionary power to allocate gains to income must also be exercised consistently and the amount so allocated may not be greater than the excess of the unitrust amount over the amount of distributable net income determined without regard to this subparagraph §1.643(a)-3(b)); (2) Allocated to corpus but treated consistently by the fiduciary on the trust's books, records, and tax returns as part of a distribution to a beneficiary; or (3) Allocated to corpus but actually distributed to the beneficiary or utilized by the fiduciary in determining the amount whichthat is distributed or required to be distributed to a beneficiary. 20www.mwe.com

21 Fiduciaries: Pro rata or "Topping Off“ included capital gains? Exception 1 of the regulations "top off" DNI with capital gains only to the extent necessary to fill in the gap between accounting income and the total distribution of "income“ in unitrust case with consistent exercise of trustee discretion (other situations less clear) Shows that different categories of income can be treated differently, despite cash being fungible and power of traditional accounting income concepts Exception 2 of the regulations appears to include capital gains proportionately with other accounting income items in DNI This can increase total taxes paid by swapping ordinary income items subject to the highest tax rate in the trust for capital gains subject to lower tax rates [however consider dividends taxed at 23.8% while short term capital gains are taxed at 43.4%] Use of entity would result in pro rata inclusion too Unclear which approach applies under Exception 3, but trustee is likely to consider available accounting income before distributing capital gains, when the capital gains distribution is discretionary [no consistency required] 21www.mwe.com

22 Fiduciaries: Are “Gross” or “Net” Capital Gains included in DNI?  Treas. Reg. sec (d): – (d) Capital losses. Losses from the sale or exchange of capital assets shall first be netted at the trust level against any gains from the sale or exchange of capital assets, except for a capital gain that is utilized under paragraph (b)(3) of this section in determining the amount that is distributed or required to be distributed to a particular beneficiary.  Does (d) say that capital losses are trapped in the trust if capital gains are allocated to DNI? In most cases, no!  Because this regulation was unchanged between the proposed and final versions, it literally does not apply in the clearest case under (b)(3) when the trustee distributes specific gains to a beneficiary.  Is there an implication that (b)(3) only applies when gross capital gains are utilized to compute the amount distributed (as opposed to net capital gains during the year being considered)? No, otherwise only a cross-reference to the subsection would be needed. 22www.mwe.com

23 Fiduciaries: Effect of swapping capital gains for ordinary income in DNI Tax Rate Reduction from a Distribution Beneficiary AGI Difference in Ord. Inc. Rates Difference in Cap. Gains RatesCost to swap CG for Ord. Inc. $ %-23.80%19.60% $ 10, %-23.80%9.60% $ 18, %-23.80%4.60% $ 46, %-8.80%9.60% $ 97, %-8.80%6.60% $ 193, %-8.80%1.60% $ 200, %-5.00%0.57% $ 372, %-5.00%1.60% $ 408, %-5.00%-1.40% $ 410, % 23www.mwe.com

24 Cumulative Trust Example  Trust with income of $140,000 in capital gains, $40,000 in rental income and $40,000 in dividends. Total income of $220,000. Trust has two orphan children as beneficiaries. Assume a $60,000 distribution per child and the child has no other income. Assume 2013 Rates and Exemptions.  Scenario I – No distribution  Scenario II – DNI does not include capital gains  Scenario III – DNI includes capital gains pro rata  Scenario IV – DNI is "topped off" with capital gains  Scenario V – All taxable income is deemed distributed 24www.mwe.com

25 Cumulative Trust Example (cont.) Tax ItemI. No Distribution II. DNI w/o CG III. DNI w/ CG pro rata IV. DNI w/ CG "top off" IV. Total Deemed Distribution Trust income tax $50,079$20,588$21,803$14,588$0 Trust NII tax$7,906$4,866$3,346 $0 Trust total tax$57,985$25,453$25,149$17,933$0 Children income tax $0$2,108$4,307$6,233$21,233 Total tax – trust and children $57,985$27,561$29,455$24,166$21,233 Effective rate26.36%12.53%13.39%10.98%9.65% 25www.mwe.com

26 How Do You Activate Business and Rental Income to Avoid NII Tax?  Active business income is determined under Code Section 469 as income from a trade or business in which the taxpayer does not materially participate  Section 1411(c)(7) also excludes from the NII Tax certain capital gain from the sale of an interest in an S Corp or Partnership owning an activity in which the seller is active  Extensive regulations under Code Section 469 address individuals and closely-held and personal service corporations, but largely ignore trusts and estates  The Code Section 1411 Regulations generally incorporate the Code Section 469 rules 26www.mwe.com

27 How does an individual materially participate under Code Section 469?  Code Section 469(h)(1): A taxpayer shall be treated as materially participating in an activity only if the taxpayer is involved in the operations of the activity on a basis which is—(A) regular, (B) continuous, and (C) substantial.  Temp. Treas. Reg. § : An individual shall be treated as materially participating in an activity for the taxable year if and only if: – (1) The individual participates in the activity for more than 500 hours during such year; – (2) The individual's participation in the activity for the taxable year constitutes substantially all of the participation in such activity of all individuals (including individuals who are not owners of interests in the activity) for such year; 27www.mwe.com

28 How does an individual materially participate (cont.)?  Seven tests (continued): – (3) The individual participates in the activity for more than 100 hours during the taxable year, and such individual's participation in the activity for the taxable year is not less than the participation in the activity of any other individual (including individuals who are not owners of interests in the activity) for such year; – (4) The activity is a significant participation activity (within the meaning of Temp. Treas. Reg. § T(c)) for the taxable year, and the individual's aggregate participation in all significant participation activities during such year exceeds 500 hours; – (5) The individual materially participated in the activity (determined without regard to this test (5)) for any five taxable years (whether or not consecutive) during the ten taxable years that immediately precede the taxable year; 28www.mwe.com

29 How does an individual materially participate (cont.)?  Seven tests (continued): – (6) The activity is a personal service activity (within the meaning of Temp. Treas. Reg. § T(d)), and the individual materially participated in the activity for any three taxable years (whether or not consecutive) preceding the taxable year; or – (7) Based on all of the facts and circumstances (taking into account the rules in Temp. Treas. Reg. § T(b)), the individual participates in the activity on a regular, continuous, and substantial basis during such year; provided the individual participates in the activity for more than 100 hours during the taxable year.  Holder of only limited partnership interest can only establish material participation under tests (1), (5) and (6) 29www.mwe.com

30 How do Code Sections 469 and 1411 play together? The Anti-PIG’s  The regulations under Code Section 469 contained much criticized rules that limited the ability of taxpayers to generate passive income to offset against passive losses. These anti-passive income generator (“PIG”) rules were criticized as “Heads IRS wins; Tails taxpayer loses” because the income from these investments would not be passive income but the losses would be passive. When passive income is recharacterized as non-passive under the anti-PIG rules, the Code Section 1411 regulations keep the non-passive character as long as the income is not further recharacterized under section 469 as “portfolio income”. See Treas. Reg. § (b)(2)(iii).  Treas. Reg sec (b)(2)(i) provides: – “To the extent that any income or gain from a trade or business is recharacterized as ‘not from a passive activity’ by reason of Regs T(f)(2) [significant participation passive activities], (f)(5) [net income from property rented incidental to developmental activity] or (f)(6) [property rented to a nonpassive activity], such trade or business does not constitute a passive activity within the meaning of [section 1411] solely with respect to such recharacterized income or gain.” 30www.mwe.com

31 How do Code Sections 469 and 1411 play together? The Anti-PIG’s (cont.)  Treas. Reg. § T(f)(2)(i) recharacterizes certain income from a significant participation passive activity (“SPPA”) as non-passive to the extent that “the taxpayer’s passive activity gross income from all significant participation passive activities for the taxable year [prior to any recharacterization] exceeds the taxpayer’s passive activity deductions from all such activities for such year.”  Treas. Reg. § T(f)(2)(ii) defines an SPPA as (i) a trade or business in which an individual participates for at least 100 hours during the taxable year and (ii) which the taxpayer does not materially participate in for the taxable year (i.e., less than 500 hours, hasn’t materially participated for 5 of the last 10 years, and participation in all SPPAs doesn’t exceed 500 hours).  With respect to each SPPA, Treas. Reg. § T(f)(2)(i) recharacterizes as nonpassive a ratable portion of the taxpayer’s net passive income from a SPPA for the taxable year determined by multiplying (i) the net passive income from the SPPA by (ii) (a) the total net passive income from all SPPAs, divided by (b) the total net passive income from SPPAs which generated net income. – NOTE: This results in netting passive income or loss from separate SPPAs first. If a loss, the loss would be passive and offset passive income from other sources for NII Tax purposes. If the netting results in income, the income would not be subject to the NII Tax. 31www.mwe.com

32 T reas. Reg. § T(g) has been reserved for regulations applying the material participation requirements to trusts and estates; therefore, the "regular, continuous and substantial" standard under IRC § 469(h)(1) applies to determine whether a trust or estate satisfies the material participation requirement The Senate Report to IRC § 469 treats a trust as materially participating "if an executor or fiduciary, in his capacity as such, is so participating....” They agree on what it says, but not necessarily on what it means: that is, what actions of the fiduciary count towards material participation by the trust or estate? How does the fiduciary materially participate? Treasury and Taxpayers Agree 32

33 IRS's Passive Activity Loss Audit Technique Guide provides: "If a business activity is owned by a trust, the examiner will need to determine if the material participation standard is met in order for losses to be fully deductible…. The IRC § 469(h) requires regular, continuous and substantial participation in the operations of the business to meet material participation and for losses to be fully deductible. There is no guidance in the regulations at this time for material participation of trusts and estates. As an administrative proxy, we look to the seven tests in Reg. § T(a) for material participation, and generally will not raise an issue if the trustee meets one of the tests. However, as a technical matter the tests apply to individuals, not to a trust or trustee. Thus, as a legal matter, the trustee must prove he works on a regular basis in operations, on a continuous basis, and on a substantial basis in operations, i.e. rise to the requirements of IRC § 469(h)." Treas. Reg. § A-3 provides material participation regulations for determining whether a decedent's estate qualifies for special use valuation (see below) IRC § 469 material participation was modeled on IRC §§ 2032A and 1402 How does the fiduciary materially participate? Taxpayers and Treasury Agree (but Treasury forgets) 33

34 Frank Aragona Trust, was decided by the Tax Court on March 27,  Decedent died owning substantial rental real estate properties that passed in trust. The children, who are the trustees, are concerned about liability risk to the other trust assets, so they contribute the real estate to a single member LLC. Three of the trustee children are active in the rental activities as employees of the LLC. The trust has other real estate businesses that are non- rental.  The IRS argued that the single member LLC should not be disregarded for this purpose, but the court does not address this issue. How does the fiduciary materially participate? Frank Aragona Trust 34

35 The IRS challenged the deductibility of the losses by the trust on two grounds: (1) the trust is not a real estate professional under IRC § 469(c)(7) excepted from PAL rules, and (2) the trustees' activities as employees could not count toward material participation by the trust The IRS argued that only individuals can perform "personal services," a requirement of the IRC § 469(c)(7) status, and that the legislative history left out trusts. The IRS argued that the trustees' actions as employees could not count toward material participation by the trust, but the taxpayer countered that the continuing fiduciary obligations of the trustees under local law even when acting as employees of the LLC The only response that the IRS could muster to the state law argument was that the managers elected to be treated as employees of the LLC for self-employment tax purposes and, therefore, were precluded from claiming to act as trustees. How does the fiduciary materially participate? Frank Aragona Trust (cont.) 35

36 Taxpayer won a total victory! Court held that a trust could be a real estate professional meaning that the trust could then show that it materially participated in its rental real estate businesses. A real estate professional must satisfy a two part test: she must participate for at least 750 hours in real estate businesses and must expend more time in real estate businesses than in all other trades or businesses. The court stated that it did not have to determine how to apply these hours tests to the trusts as the IRS failed to argue that the trust failed the hours tests. Rather, the IRS argued only that a trust cannot be a real estate professional. Commentators, therefore, sometimes can’t end that the court’s decision has less precedential significance, although as we will see below, the court actually did provide guidance on counting hours. How does the fiduciary materially participate? Frank Aragona Trust (cont.) 36

37 The court held that the trustees could count their time spent working as employees because of their fiduciary duties to the beneficiaries: “Even if the activities of the trust’s non-trustee employees should be disregarded, the activities of the trustees--including their activities as employees of Holiday Enterprises, LLC--should be considered in determining whether the trust materially participated in its real-estate operations. The trustees were required by Michigan statutory law to administer the trust solely in the interests of the trust beneficiaries, because trustees have a duty to act as a prudent person would in dealing with the property of another, i.e., a beneficiary….Trustees are not relieved of their duties of loyalty to beneficiaries by conducting activities through a corporation wholly owned by the trust.... (“Trustees who also happen to be directors of the corporation which is owned or controlled by the trust cannot insulate themselves from probate scrutiny [i.e., duties imposed on trustees by Michigan courts] under the guise of calling themselves corporate directors who are exercising their business judgment concerning matters of corporate policy.”). Therefore their activities as employees of Holiday Enterprises, LLC, should be considered in determining whether the trust materially participated in its real-estate operations. [Citations and footnotes omitted]” Despite the court’s statement that counting hours is unnecessary, the court provides a method to count hours for all purposes (including real estate professional exception and SPPA’s by considering those actions undertaken while subject to fiduciary duties owed to beneficiaries The “Money” Quote from the Aragona Trust Court 37

38 State law is clear, however, that the trustee does not elect between her role as a fiduciary or as an employee in a trust-owned business: fiduciary duties still apply See, In re Schulman, 165 A.D.2d 499, 502 (N.Y. App. Div. 3d Dep't 1991) (citing Matter of Hubbell, 302 NY 246, ; Matter of Horowitz, 297 NY 252, ; Matter of Shehan, 285 App Div 785, ), for example: "A decision on behalf of the trust to have a trustee assume a role in the corporation or other enterprise … necessarily carries with it an acceptance on behalf of the trust that the trustee's duties to it will be subordinated to any legal duties to which the trustee is subject when acting in the role of director, officer, manager, or the like. A trustee's election to a role of this type is a matter of which beneficiaries should ordinarily be informed…[t]hat duties of prudence, loyalty, impartiality (including re: income productivity), and other fiduciary duties apply to the trustee's decisions and conduct in, e.g., incorporating business or investment activities of the trust See Restatement of Trusts, 3d § 78; § 86 at comment e; Bogert, Trust and Trustees, Westlaw December 2012 Edition, § 543 (No complete elimination of fiduciary duties is possible or it ceases to be a trust) Can a Trustee Take Off Her Trustee "Hat" While She Acts As Employee, Director, Manager of a Trust-Owned Business? 38

39 What are the drafting implications of Aragona Trust? Aragona Trust Structure Frank Aragona Trust Trustees: 5 children and a lawyer – one son Anthony was disabled, Salvatore was a full-time dentist, Paul and Frank were full-time in the real estate businesses and Annette was a full-time employee of Holiday Enterprises, LLC, although not full- time in real estate apparently Beneficiaries: All of the children with income paid annually in equal shares, discretionary principal could be paid by lawyer’s direction as independent trustee Holiday Enterprises, LLC, that employed the three trustees was a disregarded entity, but that does not figure in the court’s decision. IRS argued that it should NOT be disregarded for purposes of determining material participation. How might a member-managed LLC have changed the IRS analysis? 39www.mwe.com

40 Anthony Trust Salvatore Trust Annette Trust Paul Trust Frank Trust What are the drafting implications of Aragona Trust? Separate trusts but same trustees Trustees: 5 children and a lawyer – one son Anthony was disabled, Salvatore was a full-time dentist, Paul and Frank were full-time in the real estate businesses and Annette was a full-time employee of Holiday Enterprises, LLC, although not full-time in real estate apparently Beneficiaries: Each child is a beneficiary of his or her own separate trust Each trust should materially participate under current law. Should the hours of the three active trustees have to be divided by 5 for each separate trust? No support for division. Trusts are not like individuals as they start with zero hours as opposed to individuals who start with hours. No purpose is served by requiring one trust to have different materially participating trustees from other trusts. 40www.mwe.com

41 Anthony Trust Trustees of each trust: named child and lawyer Beneficiaries: Each child is a beneficiary of his or her own separate trust Holiday Enterprises, LLC, that employed the three trustees would not be disregarded. Assume each trustee elects himself or herself to the Board of Managers of LLC Current law would cause only those trusts with materially participating trustees to materially participate What if the three active siblings became the investment advisers or protectors for each separate trust with control over the real estate business? Salvatore Trust Annette Trust Paul Trust Frank Trust What are the drafting implications of Aragona Trust? Separate Trusts with Different Trustees 41www.mwe.com

42 The "fiduciary" who must materially participate for a trust need not be the named trustee. See TAM Although the TAM held against the taxpayer, it cites the relevant authority: IRC § 7701(a)(6) defines a fiduciary as "a guardian, trustee, executor, administrator, receiver, conservator, or any person acting in any fiduciary capacity for any person." The authorities emphasize the facts, rather than titles Rev Rul Rev Rul (as modified by Rev Rul 92-51) ruled that a bank merely holding money for an estate and paying interest is not a fiduciary City Nat'l Bank & Trust Co, 109 F 2d 191 (7th Cir 1940) Although holding against the taxpayer, TAM held the "special trustee" was the fiduciary for tax purposes Who Is the "Fiduciary" for Purposes of Determining the Material Participation of a Trust? 42

43 Anthony Trust Trustees of each trust is a Private Trust Company Independent board member for each trust is the lawyer Each trust has the same real estate investment committee consisting of three children active in the real estate businesses. Would Notice apply a “look-through rule” to treat these members as the “fiduciaries”? Beneficiaries: Each child is a beneficiary of his or her own separate trust Despite Mattie Carter Trust, the IRS would have to treat the corporation’s agents and employees actions as those of the trustee and, therefore, of the trust, resulting in each trust materially participating. Salvatore Trust Annette Trust Paul Trust Frank Trust What are the implications of Aragona Trust? Separate Trusts with Private Trust Company 43www.mwe.com

44 Trust companies will rely on the activities of the agents, employees, officers, directors and managers in the trust-owned business; despite the IRS opposition to Mattie Carter Trust, which dealt only with the trust's employees and agents The closely-held corporation material participation rules under IRC § 469 supports this conclusion, but should not apply to trust companies When a private trust company acts as trustee, the actual decision-makers are considered as if they were trustees for certain tax purposes [ CB 261 (7/11/2008)] `The same result could be reached by applying the definition of "fiduciary" discussed above These individuals in the trust company also owe fiduciary duties directly to the beneficiaries of the trust under state law However, the reason for looking through the PTC to actual decision-makers is due to the need to make “tax sensitive decisions;” a purpose not applicable here Congress spoke in IRC § 42(h)(5)(B): "…a qualified low-income housing project is described in this subparagraph if a qualified nonprofit organization is to own an interest in the project (directly or through a partnership) and materially participates (within the meaning of IRC § 469(h)) in the development and operation of the project throughout the compliance period.“ Non-profit = Corporation or Trust How does a trust with a Trust Company trustee materially participate? 44

45 In Carter, the trust owned a ranch that the trustee operated through employees and agents and the opinion holds: "IRS' contention that Carter Trust's participation in the ranch operations should be measured by reference to Fortson [the trustee] finds no support within the plain meaning of the statute. Such a contention is arbitrary, subverts common sense, and attempts to create ambiguity where there is none" "It is undisputed that Carter Trust, not [the trustee], is the taxpayer. Common sense dictates that the participation of Carter Trust in the ranch operations should be scrutinized by reference to the trust itself, which necessarily entails an assessment of the activities of those who labor on the ranch, or otherwise in furtherance of the ranch business, on behalf of Carter Trust" Rethinking Mattie Carter Trust? 45

46 Is a trust a "Legal Entity" so that it acts through its agents and employees? IRS position of no agents ties back to IRC § 1402 (and §2032A), which is used to distinguish between crop share lease income that is subject to SE Tax (or not) Most trusts do not operate a business directly, but rather through an entity Mattie Carter Trust, however, does look at the entire relationship between trust and business to determine material participation, a subjective test Because trusts do not have employees and agents – trustees do – Mattie Carter should be interpreted as attributing the actions of those employees and agents to the trustees The court in Aragona Trust did not need to consider Mattie Carter, but the court appeared to consider the case favorably Rethinking Mattie Carter Trust? (cont.) 46

47 – Remove and replace current trustee (or add a co-trustee) with someone who is active in the trust-owned business – How are multiple fiduciaries treated? Without further guidance, one cannot count on aggregation of trustees’ actions. – Add another fiduciary Special trustee Adviser for special investments Director under directed trust/bank trustee – If terms of trust agreement are restrictive Court order to reform trust terms Decant if state law or instrument permits – Generation skipping tax issues What Steps Might the Trustee Take to Protect the Active Business Exception for a Family Business Held in Trust? 47

48  TAM addresses material participation under IRC § 56(b)(2)(D) (applying IRC § 469 rules). Two complex trusts and individual A owned 100% of the interests in an S corporation, which in turn owned a qualified subchapter S subsidiary ("QSub"). Individual A was special trustee of the trusts and the President of the QSub. – The issue was whether the trusts materially participated (within the meaning of IRC § 469(h)) in the activity so that R&D expenses did not need to be capitalized and amortized over 10 years by the trusts (as opposed to expensed currently) for AMT purposes under IRC § 56(b)(2)(D) – The IRS stated that the sole means for the trusts to establish material participation in the relevant activities of the S corporation and QSub was through the activities of the trust fiduciaries, in their capacity as fiduciaries – The IRS ruled that the trust did not materially participate because the day-to-day work performed by A was as an employee of the business and not in A's role as a fiduciary of the trusts, and A's time spent as special trustee did not rise to the level of being "regular, continuous and substantial" within the meaning of IRC § 469(h)(1) How did the IRS change fiduciary material participation after 25 Years? Stopped by Aragona Trust 48www.mwe.com

49 Because the trustee could only vote or sell the stock, TAM asserts that no trustee could materially participate: a unique twist on the fiduciary capacity argument IRC § 469 treats only one type of equity as significant: a limited partnership interest, because state law restricts the participation of a limited partner (LP). Thus, the Tax Court holds that an LLC member is not an LP. See Garnett v Comm., 132 TC 368 (2009), Thompson v US, 87 Fed Cl 728 (2009), and Gregg v US, 186 F Supp. 2d 1123 (D Or 2000) (same). The IRS apparently will no longer litigate the issue ( IRB) IRC § 469 places no limits on proving material participation if the taxpayer owns non- voting S corporation stock or preferred equity interests in an LLC Because IRC § 469 has only one purpose -- ensuring a taxpayer is not investing to obtain tax losses -- the nature of the equity interest is irrelevant, except an LP interest was usually the preferred form of a tax shelter If this extreme view succeeds, almost no trust could materially participate. Without apparent irony, the TAM says: "[a]n interpretation that renders part of a statute inoperative or superfluous should be avoided," despite doing exactly that with its fiduciary capacity argument The narrow view was rejected by the Frank Aragona Trust court (IRS did not appeal) How did the IRS twist the meaning of “fiduciary capacity”? 49

50 – States could amend their business statutes to allow fiduciaries to act in a business entity as director, officer or manager in that capacity Could undermine state fiduciary law – Dramatic business governance changes may be needed to provide management by owners: Member managed LLC Close corporation managed by its shareholders – The trustee, in its capacity as such, may be able to enter into a contract with the trust-owned business to provide services Services need not include management by analogy to individual rules Particularly suited if trustee is a private trust company Verify that the trusts are being compensated, rather than individual What Steps Might the Trustee Take to Protect the Active Business Exception for a Family Business Held in Trust if IRS Extreme View Prevails? 50

51 Trust Material Participation Summary  Grantor Trusts – Activities of deemed owner – Revocable trusts – Qualified subchapter S trusts – S portion only  Non-Grantor Trusts (including ESBTs) - Activities of fiduciaries Individual Trustees Special Trustee – degree of discretionary power to act for trust – TAM Corporate Trustee (Bank Trustee or Private Trust Company) – whether and how? Employees and agents – Mattie K. Carter Trust v. United States  Nature of activities undertaken – investor v. day-to-day management  Activities undertaken in "capacity as such" – PLR vs. TAM (broad vs. narrow interpretation)  The authorities all support considering all of the trustees actions in whatever capacity rendered in the business, only recent IRS guidance and argument are to the contrary.

52 The Preamble provides: The Treasury Department and the IRS believe that the commentators have raised valid concerns about fiduciary material participation. The Treasury Department and the IRS considered whether the scope of these regulations should be broadened to include guidance on material participation of estates and trusts. The Treasury Department and the IRS, however, believe that this guidance would be addressed more appropriately in the section 469 regulations. Further, because the issues inherent in drafting administrable rules under section 469 regarding the material participation of estates and trusts are very complex, the Treasury Department and the IRS believe that addressing material participation of trusts and estates at this time would significantly delay the finalization of these regulations. However, the issue of material participation of estates and trusts is currently under study by the Treasury Department and the IRS and may be addressed in a separate guidance project issued under section 469 at a later date. The Treasury Department and the IRS welcome any comments concerning this issue, including recommendations on the scope of any such guidance and on specific approaches to the issue. How might the Final Code Section 469 regulations approach fiduciary material participation? 52

53 Whose actions are relevant to determining a trust’s material participation? The IRS says the fiduciary’s and Mattie Carter says all of the trust’s fiduciary’s, employees and agents Decedent’s activities relevant to estate or revocable trust qualification Who is a fiduciary? Not just the trustee but whomever the actual decision-maker over the business acting in a fiduciary capacity What actions of the fiduciary are relevant towards determining the trust’s material participation? State law and tax authorities say all and the IRS most recently has disagreed What measure of the fiduciary’s actions are sufficient for the trust to materially participate? Objective (Aragona Trust counts hours) vs. Subjective test (Mattie Carter considers all factors and allows attribution) Do the individual tests apply? Parity? Aggregation of actions by multiple fiduciaries? What are a few questions the new regulations may answer? 53

54 Grantor Trust (discussed above) Qualified subchapter S trust ("QSST") – Treated as a grantor trust of beneficiary as to S corporation stock it owns – Special treatment of sales of S corporation stock (reproposed regulations provide simpler rules) – Proposed regulations create problems for sales if trustee does not materially participate Electing small business trust ("ESBT") (discussed below) Certain transitional trusts created at, or becoming irrevocable due to, an individual's death, whose eligibility is temporally limited – Subject to the ordinary fiduciary income tax rules With the exception of transitional trusts, S Corp Trusts do not carry out DNI by distributions so the character of distributed income need not be reevaluated Which trusts own eligible S corporation stock? 54

55 How are electing small business trusts ("ESBTs") taxed?  Section 641(c)(1) provides that the portion of the ESBT that holds S corporation stock ("the S portion") shall be considered a separate trust from the remainder of assets held in the ESBT ("the non-S portion")  For section 1411 purposes, the UNII from the S and non-S portions of the trust are calculated separately and then combined  An ESBT will then be considered a single trust when determining if the trust has AGI above the threshold amount  The trust's AGI for threshold purposes is calculated by combining the AGI of the non-S portion of the trust with a single item of ordinary income from the S portion (after taking into account all deductions, carryovers, and loss limitations)  The trust's NII tax will then be paid on the lesser of the total UNII or the trust's total AGI above the threshold amount  See Example in Treas. Reg. § (c)(3) 55www.mwe.com

56 How does a fiduciary determine the character of distributed income?  Business income from Tax Partnerships is characterized by distributions so does the fiduciary’s material participation or the beneficiary’s material participation determine whether the distributed income is active?  Without much comment, Treas. Reg. sec (e)(3)(ii) provides that the character of active or passive at the trust level will carry out to the beneficiary of the trust if distributed: – “If one or more items of net investment income comprise all or part of a distribution for which a deduction is allowed …, such items retain their character as net investment income … for purposes of computing net investment income of the recipient of the distribution….” [cross-references omitted]  This regulation prevents trustees from avoiding the uncertainty of the application of Code Section 469 to trusts by distributing the business income of the trust to beneficiaries who materially participate in the business under the individual rules or distributing rental income to beneficiaries who are real estate professionals. 56www.mwe.com

57 Did the Government Follow Its Own Policy with the 1411 Character Rule?  The income distributed to the beneficiaries retains its “character” under Subchapter J. For example, tax-exempt interest is included in DNI. When distributed to the beneficiaries, it remains tax-exempt interest. Business income earned by the trust included in DNI and allocated to a beneficiary should remain business income. Some argue that this character rule requires active or passive income of the trust to remain so when distributed to beneficiaries, but that treatment is not certain. Treasury Regulations section 1.652(b)-1, provides: – The tax treatment of amounts determined under §1.652(a)-1 depends upon the beneficiary’s status with respect to them not upon the status of the trust. Thus, if a beneficiary is deemed to have received foreign income of a foreign trust, the includability of such income in his gross income depends upon his taxable status with respect to that income.  Treas. Reg. sec contains no comparable statement, but the character rule applies to complex trusts too. See Rev. Rul , C.B www.mwe.com

58 Does Code Section 469 provide any guidance?  A beneficiary has an equitable ownership in trust assets under state law. However, the existing Code Section 469 regulations ignore this ownership interest. Treas. Reg. sec regulation on grouping activities provides as follows: – (a) Scope and purpose. This section sets forth the rules for grouping a taxpayer’s trade or business activities and rental activities for purposes of applying the passive activity loss and credit limitation rules of section 469. A taxpayer’s activities include those conducted through C corporations that are subject to section 469, S corporations, and partnerships.  Treasury Regulations section (f) complicates using the beneficiary’s material participation to characterize distributed income: – [A]ny work done by an individual (without regard to the capacity in which the individual does the work) in connection with an activity in which the individual owns an interest at the time the work is done shall be treated for purposes of this section as participation of the individual in the activity. 58www.mwe.com

59 What other factors may effect the classification of distributed income?  Recharacterization rule for an active beneficiary (passive trust income becomes active)?  Transitional rule that may come from new regulations related to the death of a decedent or change between grantor and non-grantor trust status?  Depreciation and depletion ordinarily apportioned outside of DNI, but apportionment may be restricted by Code Section 469 to allow directly to a beneficiary only if the trustee is active in the trust owned business? 59www.mwe.com

60 Tax StatusS CorpState Law LPOther Tax Partnership Trust Self- Employment Income Salary Payments only, but not K- 1 income Guaranteed payments for services and GP K-1 income Disputed, but likely all K-1 income Trustee Fees (at most) Active under IRC § 469 Type of stock does not matter; material participation under any of 7 tests LP may materially participate only under 3 of 7 tests Disputed, but most likely able to qualify under any of 7 tests Before Aragona Trust unclear due to IRS "fiduciary capacity" argument; may change with new regs Subject to NII Tax Passive or trading K-1 income Passive or Trading K-1 income How are different entities treated for NII Tax and SE Tax purposes? 60


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