InvestmentNews Features McManus Column for The Tax-Conscious Adviser

Below is an advice column on capital gains tax strategies by John O. McManus that was published by InvestmentNews for its regular feature, “The Tax-Conscious Adviser.”

Investment News



tax concious adviser

Estate plans require a fresh look

Thinking around bequests shifts as capital gains tax and estate tax exemption rise

Nov 29, 2015 @ 12:01 am

By John O. McManus

Significant tax law changes mean it’s time to dust off your estate plan. Long-term capital gains tax rates now range from 25% to 33%, with the combination of the top federal, state and local rates and the Medicare surtax. This hike in capital gains tax rates, coupled with the greater federal estate tax exemption, calls for a fresh look at planning strategies.

With the current $5.43 million federal estate tax exemption ($5.45 million for 2016), many people may no longer be exposed to federal (and possibly state) estate taxes. Thus, maneuvering around capital gains tax becomes the primary concern.

While basis is typically the purchase price less adjustments, basis can change or jump upward significantly upon inheritance, which is called a “step-up in basis.” With a step-up in basis, the value of the asset is determined to be the market value of the asset at the time of the step-up.

Historically, practitioners moved assets out of the individual’s estate while that individual was alive to avoid estate tax. However, when assets are gifted during a lifetime, the step-up in basis is not deployed. When assets are included in an estate, they may be subject to estate tax (in today’s environment, not always), but certainly the assets in the estate enjoy a step-up in basis and significant gains tax can be avoided.


How does one employ a step-up in basis when assets have already been irrevocably transferred during lifetime, theoretically surrendering the opportunity to obtain a step-up in basis? One strategy may be to intentionally undermine a prior gifting plan so that assets can be included in the estate to achieve the step-up in basis upon death, particularly if those assets would not otherwise be subject to estate tax.

Next, transferring an asset “up-stream” to a trust for the benefit of the donor’s parents allows an asset to get a step-up in basis upon the parents’ death and then the asset passes back to the donor or his or her descendants in trust. The asset could then be liquidated free of capital gains tax.

Another potentially avoidable problem is tied to older Americans each owning a half interest in their primary residence. After one spouse passes away, the surviving spouse may wish to sell the real estate, but only half of the property received the step-up obtained from the deceased spouse. Trying to move the entire residence to the infirmed spouse’s name prior to death is clever, but the IRS has significant restrictions. What you can do is employ a community property trust with a home (or situs) in Alaska or Tennessee, a joint-exempt step-up trust (JEST), or estate trust while both spouses are not facing imminent death. These moves can provide the benefit of a step-up in basis on the entire residence upon the passing of the first spouse, so the surviving spouse can sell the appreciated asset without the imposition of any capital gains tax.

The tax code permits owners of homes to exclude up to $250,000 of capital gain if they have owned and lived in their home for at least two years out of the five years before a sale. For a married couple, the amount is $500,000. With this strategy, one may be able to exclude some or all of the gain that is taxed on the sale of one’s principal residence. If a surviving spouse sells the home in the year their spouse passes away, they can still file jointly and use both exemptions.


When working with investment property including residential rentals, a 1031 exchange enables one to postpone the capital gains taxation by rolling over the sale proceeds into a new investment. A separate corporation needs to be set up to receive the sale proceeds and make the new purchase (all within a short period of time of each other), but it is a wonderfully effective strategy.

Finally, when gifts of appreciated long-term assets are made to charity, no capital gains taxes are owed, because they are donated to charity, not sold in the donor’s name. If you’re holding securities with a loss, it’s better to sell them first, then take the capital loss for tax purposes, and thereafter donate the cash. A charitable remainder trust allows you to make the gift, retain an annuity stream back to the donor in a tax-efficient manner and later contribute it to a charitable entity run by the family making donations to favorite charities.

John O. McManus is an estate planning attorney and the founding principal of McManus & Associates.