Estate Planning

Category Archives

Are Generational Split Dollar Plans Still Viable?

Generational split dollar plans remain an extremely powerful planning strategy that, even without the benefit of deep discounts, can address non-tax liquidity needs, and act as an estate freeze technique for the first generation.

To learn more, check out this article by Highland Capital Brokerage’s very own Robert Finnegan, J.D., CLU®, AEP®, that was published in the January 2019 edition of Estate Planning magazine.

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De-risking a Concentrated Stock Position


It’s so simple it’s scary.

Clients with a concentrated stock position that is intended to transfer to family and/or charity may be able to potentially increase the per share value of the transfer while de-risking the portfolio by using life insurance.


It’s so simple it’s scary.

The Twelve Ways of Gifting

In the spirit of the holiday season, here’s a run-down of The Twelve Days of Christmas.

Oops, I mean The Twelve Ways of Gifting…

IRS Announces “No Clawback” of Gift Tax Exemption Amount

On November 20, 2018 the IRS issued proposed regulations (expected to be passed) clarifying that the estate/gift tax will not apply to gifts made before 2026, when the amount that can be sheltered from the tax is higher, as provided for by the 2017 Tax Act.

Squeezing Liquidity Out of Commercial Real Estate Assets

Do you have clients who have significant holdings in illiquid commercial real estate but little cash to fund their life insurance needs?

If so, commercial real estate can be used to pay the annual premium.

6 Takeaways from Cahill Tax Court Case: Intergenerational Split Dollar

The recent Estate of Cahill tax court case gives us a glimpse into the court’s view of intergeneration split dollar arrangements (GSD). In particular, the court focused on, among other things, the valuation of the loan repayment for estate tax purposes, as well as the appearance of the transaction as a vehicle for below market transfers to family members. Although the tax court did not issue a summary judgement and the case will now move to trial for a decision, the comments of the tax court are telling.

Estate Planning: The Cost of Waiting

Following the 2017 Tax Act, many advisors have asked how to respond to clients who say that there is no urgency in planning given the tax changes. To address this lack of urgency, consider the following:

  • the non-tax needs of the family–including liquidity to equalize gifts among heirs,
  • the preference heirs may have to buy each other out of unwanted assets, and
  • the desire to ensure long-term care for a special needs family member.

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