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Probate & Trust Law Section Conference Manual ... - Minnesota CLE

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Summary of Option Strategies<br />

Strategy Description Purpose(s) Income Tax Effects Transfer Tax Effects Issues/Comments<br />

1. Early exercise Exercise of options before Conversion of ordinary income<br />

None<br />

expiration<br />

into capital gain<br />

2. Gift to descendants Holder gives options to<br />

descendants; typically limited to<br />

vested options; gifts of unvested<br />

options possible with tax risks<br />

3. Gift to trust for<br />

descendants<br />

4. Gift to family<br />

limited partnership or<br />

LLC<br />

Same as 2, except that donee is<br />

trust for descendants, preferably<br />

administered by independent<br />

trustee<br />

Same as 2, except that donee is a<br />

partnership/LLC composed of<br />

family members and entities<br />

Transfer of wealth to next<br />

generation in a manner that<br />

reduces potential estate tax<br />

burden if option position (or<br />

resulting stock) were held until<br />

death<br />

Same as 2, except resulting<br />

wealth will be held and<br />

administered by independent<br />

trustee<br />

Same as 2, except resulting<br />

wealth will be held and<br />

administered by managing<br />

partner or member of<br />

partnership/LLC<br />

Triggers ordinary tax on option<br />

exercise; future gains taxed as<br />

capital gains<br />

None at gift; donor pays ordinary<br />

tax on option spread when<br />

options exercised by donees;<br />

donees pay capital gains tax on<br />

gains beyond fair market value<br />

(FMV) of stock at exercise<br />

Same as 2, except trust pays<br />

capital gains tax on gains<br />

accruing after exercise; if trust is<br />

“grantor” trust, taxation of gains<br />

(and other income) is shifted to<br />

donor<br />

Same as 2, except<br />

partners/members pay capital<br />

gains tax directly on gains<br />

accruing to partnership/LLC after<br />

exercise<br />

Gift taxes imposed, subject to<br />

applicable exclusions and credits,<br />

on FMV of options at gift;<br />

options removed from estate tax<br />

exposure at value lower than that<br />

projected at death; estate tax also<br />

reduced by ordinary tax paid by<br />

donor at exercise, plus foregone<br />

growth thereon; options’ FMV<br />

includes spread and time (e.g.,<br />

Black-Scholes) value, but<br />

discounts from this value should<br />

be available if confirmed by<br />

appraisal<br />

Same as 2; but if trust is<br />

“grantor” trust, holder’s retention<br />

of income tax obligation<br />

produces additional estate tax<br />

savings (by reducing ultimate<br />

taxable estate)<br />

Same as 2<br />

“Conversion” is really an<br />

illusion; initial tax burden<br />

reduces future increases by<br />

similar amount, but future<br />

increases also subject to capital<br />

gains tax; can work<br />

if taxes and costs are borrowed<br />

and rate of increase is high<br />

enough to overcome extra capital<br />

tax burden; otherwise, holding<br />

options should be superior on<br />

after-tax basis<br />

Option plan must allow gifts;<br />

control over exercise shifts to<br />

donees, but income tax burden<br />

remains with donor – good estate<br />

tax planning, but donor’s<br />

liquidity and lack of control must<br />

be addressed; gifts of unvested<br />

options risky since IRS ruled that<br />

gift tax is deferred until options<br />

vest (at FMV then existing);<br />

valuation of options and<br />

associated discounts subject to<br />

IRS challenge; if stock does not<br />

perform, credits applied to gift<br />

tax could be lost<br />

Same as 2, but control over<br />

option exercise and resulting<br />

stock held by independent trustee<br />

Same as 2, but control over<br />

option exercise and resulting<br />

stock held by managing<br />

partner/member of<br />

partnership/LLC; if donor retains<br />

an interest in partnership/LLC,<br />

possible ordinary tax measured<br />

by value of retained interest at<br />

contribution<br />

CONFIDENTIAL<br />

1

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