Category Archives: Capital Gain Transactions

New IRS Guidance Makes Opportunity Zone Tax Break More Desirable

The Internal Revenue Service has issued updated regulations regarding the Opportunity Zone tax break created by the 2017 tax reform legislation. Investors have proven slow to seek Opportunity Zone investments because of ambiguities and a lack of details in The Tax Cuts & Jobs Act statute and the limited scope of initial guidance issues in October 2018. The new guidance is more sweeping and offers more definite answers to many of the open questions.

Opportunity Zone investments offer two tax benefits:

  • Deferral of capital gain recognition on other assets sold before an Opportunity Zone investment until earlier of (1) sale of the new investment or (2) December 31, 2026.
  • 100 percent elimination of capital gain on the Opportunity Zone investment itself, if held more than 10 years, or reduction of capital gain if held at least five, but not greater than 10 years.

Requirements exist regarding investment timing, legal structure, and investment characteristics. The program generally favors taxpayers with reliable access to emergency liquidity and a longer-term investment horizon.

View the IRS announcement which includes detailed guidance.

E. John Wagner, II

For Want of a Nail? How Long-Term Capital Gain Eligibility Can Turn on a Single Piece of Paper

An old proverb teaches that the absence of a horseshoe nail can cause the downfall of a kingdom. A recent Tax Court cases suggest a real estate owner’s eligibility for long-term capital gain can turn on something just as trivial:  a single piece of paper.

The Sugar Land case involved real estate businesspersons who, though various entities, held some land for investment purposes and other land for development purposes. During 2008, they decided to abandon development plans for raw land they originally intended to develop. In 2008, they executed an owner resolution expressing their change of intent. Their land holding company subsequently sold most of the property to an unrelated homebuilder in three transactions in 2011 and 2012. The company then sold substantially all the remaining property to related entities in four transactions spanning 2012 through 2016. The related entities developed that land for resale.

The IRS asserted that the 2012 sales should have generated ordinary income instead of long-term capital gain. Despite several factors militating against capital gain eligibility—including nearby development activity by related entities–the Tax Court found that the sales qualified as long-term capital gain. The court identified the 2008 owner resolution as the critical factor showing their intent.

The Sugar Land opinion is a bookend to the Fargo case we discussed in 2015. In Fargo, the Tax Court held that a taxpayer who held land without developing it for over a decade recognized ordinary income on its sale. The court reasoned that the long holding period did not overcome the absence of an owner resolution or other documentation evidencing the abandonment of the owner’s original development plan. The taxpayer could not recognize long-term capital gain.

Lesson learned? Silly or not, documenting the non-development intent for holding raw land can make a big difference in the income tax bill when the property is sold. If you want long-term capital gain, take a few minutes to make sure the owners execute a contemporaneous resolution or governing documents expressing the intent to hold the property for investment, not development. Otherwise you might tell a tale of losing your own financial kingdom, for want of just one piece of paper.

Helpful Resources:

E. John Wagner, II

Welcome the New Year With Our Updated Tax Reform Review

On December 22, 2017, President Trump signed into law the most important rewrite of the US tax code in decades. The federal law, which is entitled “An Act to provide for reconciliation pursuant to titles II and V of the concurrent resolution of the budget for the fiscal year 2018” (the Act), has no other name, as its short title, the Tax Cuts and Jobs Act, was stricken from the bill shortly before being signed.

We have prepared a summary of the Act as a non-exhaustive discussion of key changes to the tax code. We will continue to analyze the Act and will post updates and recommend planning strategies on this blog.

For more information regarding the Act, please see our previous related blog posts linked below:

On behalf of everyone at Williams Parker, we hope you and your family have a healthy and happy 2018.

Please note this post was co-authored by Elizabeth Diaz, Colton Castro, and Nicholas Gard. 

Elizabeth P. Diaz

Colton F. Castro
(941) 329-6608

Nicholas A. Gard
(941) 552-2563

UHF Antennas Become Even More Obsolete, But Broadcasters Get a Tax Break

Remember adjusting an oddly shaped TV antenna to improve reception on channels higher than 13?  If you do, the memory is likely distant.

Congress noticed a few years ago and mandated that the Federal Communications Commission (the “FCC”) repurpose Ultra High Frequency (a.k.a. “UHF”) broadcast spectrum that carried some of those channels, to create more room for mobile broadband.  The FCC gave licensees holding rights to the repurposed spectrum the option of selling their existing licenses or accepting inferior rights.

One licensee wanted to sell and reinvest in other rights of their choosing without paying capital gains tax on the sale. The licensee asked the Internal Revenue Service to rule that Internal Revenue Code Section 1033, the same provision that allows tax-free reinvestment when the government takes real estate by condemnation, applies to allow tax-free reinvestment of the UHF license rights.  The IRS agreed, even though the taxpayer technically was not forced to sell. The IRS ruled that the option to accept other rights did not prevent Section 1033 tax deferral because the inferiority of the substitute rights the FCC offered justified ignoring that alternative. The IRS found the transaction amounted to a forced sale and therefore qualified for tax deferral.

If the government gives you a “false” choice between selling your property or accepting an inferior alternative, this ruling explains how to defer tax on the sale if you reinvest the proceeds. But we do not recommend trying this strategy with your old UHF TV antenna. You probably won’t recognize gain to defer anyway.

Here is a link to the IRS ruling:

E. John Wagner, II

Post-Election Flashback: A Tax Break For Federal Executive Office Appointees

With President-elect Donald Trump’s cabinet appointments at the forefront, we revisit our August 2016 post examining a capital gains tax break for federal executive appointees who must sell assets to avoid conflicts of interest.  We noted that appointees with unrealized capital gains in undiversified assets could use the law to diversify without paying capital gains tax, creating a tax break vastly more valuable than anything else they earn from their positions.

Here is a link to our original post:

Here is a link to a November 8 International Business Times article quoting our post and further examining the tax deferral law:

Are any potential Trump appointees likely to benefit?  Decide for yourself after reviewing a roster of potential appointees:

E. John Wagner, II

Want to Diversify an Appreciated Asset Position Without Paying Capital Gains Tax? Take a Federal Government Job With a Conflict of Interest.

If you want to convert a substantially appreciated asset into a diversified asset portfolio without paying capital gains tax, choose your favorite Presidential candidate with extra care.   He or she could save you a lot of tax by giving you a job.

If that candidate becomes President, appoints you to an Executive Branch position, and determines owning the appreciated asset creates a conflict of interest in your new Executive Branch job, Internal Revenue Code Section 1043 allows you to sell the appreciated asset and buy a diversified investment portfolio or Treasury Securities without paying the capital gains tax. Judicial appointees enjoy a similar opportunity.

Sound crazy? In 2006, media speculated that former Goldman Sachs CEO Hank Paulson would use Section 1043 to avoid millions of dollars of capital gains tax from selling appreciated Goldman Sachs stock when President George W. Bush appointed him Treasury Secretary. One might expect the tax benefit far exceeded the value of Mr. Paulson’s salary and other compensation.

But Section 1043  isn’t a complete “win” for the appointee. The gain is only deferred, not permanently eliminated, so the appointee must recognize the gain and pay the capital gains tax if and when he or she sells the newly purchased investments.  Also, diversification isn’t always voluntary.  As a condition to confirming his or her appointment, a Congressional committee can require an appointee to sell an asset the appointee wants to keep.  Another noteworthy consideration: these jobs aren’t necessarily easy.  One can wonder if, given a crystal ball, Mr. Paulson would rather have paid the capital gains tax, than serve as Treasury Secretary in the early days of the the Great Recession and, as a Republican, drop to a knee before the Democratic Congressional leadership to beg support for rescue legislation in the midst of financial crisis.

Nevertheless, don’t hesitate to raise an eyebrow if our future President appoints someone with a lot of gain (to defer) to an Executive Branch position. And if you find a job attractive in part for its tax perks, take heart that you aren’t necessarily the first person to submit your resume under such circumstances.

Here is a link to Internal Revenue Code Section 1043:

Here is a link to a 2006 Forbes article discussing Mr. Paulson’s tax situation and some quirks to Section 1043 in more detail:

Here is a link to 2008 coverage of Mr. Paulson’s kneel:

E. John Wagner, II

IRS Court Victory in Capital Gains Case May Help More Taxpayers Than it Hurts

Most capital asset classification cases involve the IRS denying lower-tax-rate capital gain treatment.  Many of these cases turn on whether a taxpayer’s activities relating to the asset were minor enough to avoid becoming an active “business” rather than a more passive activity.

A recent case turned that pattern on its head, with a taxpayer claiming a real estate asset he intended to redevelop was a business asset, not a capital asset, so he could deduct a loss on its sale against other ordinary income.  The IRS argued the taxpayer didn’t sell real estate frequently enough to make his activity a business.  The IRS further argued the loss should be a capital loss that is not deductible against other ordinary income.

The Tax Court agreed with the IRS.  In its opinion, notwithstanding the taxpayer’s primary occupation as an employee of a real estate development company,  the Tax Court ignored the possibility that the taxpayer could be in the business of developing property himself.  The court instead focused solely upon whether he frequently personally purchased and sold property.

The taxpayer’s infrequent personal real estate dealings helped the IRS disallow a loss in this case; however, the Tax Court’s reasoning could be beneficial to other taxpayers with gains.  For example, it could help persons who occasionally develop property—such as a spec home–as a non-primary activity in claiming lower-tax-rate capital gain treatment.  In the end, more taxpayers may benefit from this decision than are hurt.

Here is a link to the Tax Court’s Memorandum Opinion in Evans

E. John Wagner, II

Some Tax-Motivated Couples Don’t Marry Under the Law, Even If They Are Bound In Their Hearts

The Supreme Court’s decision authorizing nationwide same-sex marriage further extends marital rights. But some extraordinarily-tax-motivated same-sex couples may make the same choice that some opposite-sex couples have made for years, to avoid marriage to take advantage of tax planning opportunities married couples cannot.

Marriage brings with it many tax benefits, especially under the federal income tax for families of all income levels with a single wage earner, and under the federal estate and gift tax, where even wealthy spouses are allowed unlimited tax-free transfers between themselves. But married couples are also treated as “related parties” under the Internal Revenue Code. Related party treatment prevents spouses from engaging in many tax motivated transactions that unmarried persons—even those who for all practical purposes function like a married couple—cannot.

For example, unmarried persons who co-own a corporation can more freely engage in redemption transactions in which their corporate share income tax basis offsets distribution income. Married couples are more restricted in this regard. Unmarried persons can buy and sell property between themselves free of related-party rules that re-characterize lower-tax long-term capital gain as higher-tax-rate ordinary income or prevent the purchaser from re-depreciating purchased assets. Members of unmarried couples can serve as counterparties in tax-deferred 1031 exchanges, whereas married couples are restricted in this regard.

The number of persons who would avoid marriage for tax reasons is limited. In our experience, however, some individuals—particularly those with substantial real estate holdings–take these tax planning opportunities into account when deciding whether to marry under the law, even if they are committed in their hearts. Those taxpayers turn Congressional policy on its head, causing tax laws intended to prevent abusive tax avoidance by closely connected individuals into an unintended deterrent to marriage.

E. John Wagner, II

Real Estate Investor Forced to Recognize Ordinary Business Income Instead of Capital Gain, Despite Holding Property Without Physical Improvement For Over a Decade

Sometimes it’s what you say, not what you do, that matters. A taxpayer learned that the hard way in a recent United States Tax Court decision.

There are numerous court decisions in which a taxpayer acquired property, incurred “soft costs” to entitle the property for future development, and then recognized capital gain (not higher-tax ordinary income) on the sale of the property. In these cases, the taxpayer did not physically improve the property, and the taxpayer by resolution, agreement, prior tax reporting, or other independent means expressed an intent to sell the property before physical improvement occurred. Amongst other factors, the combination of an expressed non-development intent with the actual lack of physical improvement was sufficient to preserve capital gain treatment, and to prevent the taxpayer’s activities from becoming a more active “business” subject to higher ordinary income tax rates. This sometimes has been true even when the taxpayer sells the property to another company with common ownership, which then develops the property.

The recent Tax Court decision emphasizes that the expression of intent is essential to preserving capital gain qualification, even if property is never developed or improved. In the case, the taxpayer originally intended to develop the property. The taxpayer incurred soft costs to prepare the property for development, but then held the property for over a decade without physically improving it. The taxpayer rented and occupied the property as office space, uses usually considered capital gain-qualifying activities. The Tax Court nevertheless held that the absence of evidence the taxpayer abandoned its initial development intent was sufficient to distinguish the case from others in which taxpayers engaged in the same activities, but specifically expressed non-development investment intent to third parties.

While the decision seems harsh, it is a reminder that the characterization of a taxpayer’s activities in partnership or operating agreements, resolutions, business coding on tax returns, and other third-party pronouncements is essential to protecting capital gain qualification, even if a taxpayer never physically develops property.

Here is a link to the United States Tax Court decision in Fargo v. Commissioner:

E. John Wagner, II

Better to Abandon a Bad Investment Than to Sell It? Sometimes, if the Investment is Still Worth Something

Could it be better to abandon a bad investment and receive nothing in return, than to sell it and receive something in return? Sometimes the answer is “yes,” according to a recent federal appellate court decision. The reason is that you can take an ordinary business tax loss from abandonment even though a sale would produce a capital loss. The extra tax benefit from the ordinary business loss may be more valuable to you than the combined consideration and capital loss you receive from a sale.

Assume you bought an investment for $100, and its value has fallen to $2. If you sell the investment for $2 and the investment is a capital asset, you will recognize a $98 capital loss. Unless you have $98 of capital gains from other transactions available at that time, you can’t use the loss to offset other income, and you are left with the $2 of sale proceeds. Even if you have $98 of capital gains from other transactions, an individual might offset capital gains tax at a 23.8% tax rate, producing a $23.32 tax savings, and a total value of $25.32, including the $2 of sale proceeds. If you abandon the investment for no consideration, you may be able to take a business loss offsetting income otherwise taxable at a 43.4% tax rate, producing a $42.53 tax benefit. Bizarrely, the $42.53 tax benefit from the ordinary business deduction is worth substantially more than the $25.32 combined proceeds and capital loss tax benefit from a sale.

Even more bizarrely, thanks to a quirk in the Internal Revenue Code, this arbitrage is not possible when the investment is completely worthless. It is only possible when the investment has some remaining value.

This arbitrage only exists in limited circumstances, and does not work for all investments. It also has litigation risk. The Tax Court has held that it does not work. The Fifth Circuit Court of Appeals decision approving the strategy is only binding law to overturn the contrary Tax Court decision in Texas, Louisiana, and Mississippi. The IRS may still challenge the strategy for taxpayers in other states, and those taxpayers cannot be sure their own federal appellate court will agree with the Fifth Circuit. For those willing to take those risks, however, the strategy is compelling.

Here is a link to the Fifth Circuit Court of Appeals February 25, 2015, decision in Pilgrim’s Pride v. Commissioner, approving the strategy:

E. John Wagner, II