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ESTATES, TRUSTS & GIFTS




         the agreement. The court indicated that   not a trustee of this trust. In Cahill and   family members). In Levine, the court
         the IRS’s position failed to consider Lar-  Morrissette, the decedent held the power   suggested that if the fiduciary’s duties
         son’s fiduciary obligations owed to the   in conjunction with others, triggering   were “nonconflicting” (i.e., where the du-
         beneficiaries of the insurance trust.  the application of Secs. 2036(a)(2) and   ties held in one fiduciary capacity would
           Distinguishing the Levine facts from   2038. In Morrissette, the estate ultimately  not require the fiduciary to act against
         those in other cases in which the Tax   prevailed because the Tax Court deter-  his or her duties as a fiduciary in another
         Court took issue with fiduciary duties in   mined that the bona fide sale exception   capacity), they are not “illusory” and
         the context of a family limited partner-  to Secs. 2036 and 2038 applied. Cahill   should be respected. Although Levine
         ship (FLP) as being “illusory,” the court   involved a motion for summary judg-  did not involve an FLP, the opinion’s
         noted that Larson owed nonconflicting   ment on the estate’s arguments that   discussion of fiduciary duties from a Sec.
         fiduciary duties both to the beneficiaries   Secs. 2036, 2038, and 2703 did not apply  2036(a)(2) perspective may be a positive
         of the insurance trust and to Levine as   to the split-dollar arrangement, which   development for the evaluation of FLPs.
         an attorney-in-fact. In both Strangi7 and   the Tax Court denied (therefore, further
         Powell,8 the fiduciary’s role as attorney-  proceedings will determine whether   Gift tax
         in-fact could have required him to act   the estate ultimately prevails). Levine   Transfer via spouse held an
         against his duties as trustee, the court   provides an example of how to structure   indirect gift to trust
         explained. Finding it more likely than   split-dollar arrangements to avoid Secs.   In Smaldino,10 the Tax Court held
         not that Larson’s fiduciary duties limited   2036 and 2038 altogether — and not   that a gift to the taxpayer’s spouse was,
         his ability to cancel the life insurance   have to rely on the bona fide sale excep-  in substance, an indirect gift to a trust
         policies, the court concluded that the   tion to avoid estate tax inclusion of the   for the benefit of the taxpayer’s heirs.
         cash-surrender values of the life insur-  cash-surrender values.      At the time of the trial, Louis P.
         ance policies should not be included in   The IRS had also raised the Sec.   Smaldino owned an $80 million real
         Levine’s estate under Sec. 2036(a)(2).  2703 issue in Morrissette and Cahill. In   estate portfolio. He married Agustina
           Sec. 2703: Finally, the Tax Court   Morrissette II, the Tax Court determined   Smaldino in 2006. Mrs. Smaldino had
         rejected the IRS’s assertion that the   that the exception to the application of   worked for her husband’s business since
         special valuation rules under Sec. 2703   Sec. 2703 was met under the facts of the   1995. In 2012, Mr. Smaldino turned 69
         applied to the split-dollar arrangement   case and, therefore, Sec. 2703 did not   and, after a health scare, decided to get
         at issue. When Levine entered into   apply. In Cahill, the Tax Court denied   his estate affairs in order. At the time,
         the split-dollar arrangement, the IRS   the estate’s motion for summary judg-  Mr. Smaldino had six children from a
         contended, she effectively restricted her   ment on the issue. In Levine, the Tax   prior marriage and 10 grandchildren.
         right to control the $6.5 million and   Court determined that it was not an   Mr. Smaldino owned and operated
         the insurance policies, but this restric-  issue because she did not own the life   his real estate portfolio through limited
         tion on her right to access the $6.5   insurance policies at her death (because   liability companies (LLCs) held in a
         million should be disregarded under   she had not retained an interest in the   revocable trust. One of these entities,
         Sec. 2703(a)(2). Levine’s estate argued   policies via Sec. 2036 or 2038).  Smaldino Investments LLC, held 10
         that Sec. 2703 applied only to property   The Tax Court has questioned the   rental properties. In 2013, he transferred
         Levine owned when she died, and the   strength of fiduciary duties in the con-  roughly 8% of the LLC’s class B mem-
         court agreed.                     text of family arrangements — distin-  ber interests to a trust he had created a
           The key to the estate’s successful   guishing these arrangements from those   few months earlier for the benefit of his
         defense of not including the cash-  at issue in the Supreme Court’s holding   children and grandchildren. The value
         surrender values of the life insurance   in Byrum,9 (respecting fiduciary duties   of these interests equaled his remaining
         policies at Levine’s death was that   that a majority owner of stock owes to   gift tax exemption (approximately $1
         she did not have the power under the   its minority owners). This is especially   million). Mr. Smaldino also transferred
         split-dollar arrangement, solely or in   true in the context of FLPs and the   roughly 41% of the LLC’s class B mem-
         conjunction with others, to terminate   fiduciary duties that a general partner   ber interests to Mrs. Smaldino, the value
         the arrangement. Only the insurance   (usually held by senior family members)   of which roughly equaled her remain-
         trust had that power, and Levine was   has to its limited partners (usually junior   ing gift tax exemption (approximately


          7.  Estate of Strangi, T.C. Memo. 2003-145.        9.  Byrum, 408 U.S. 125 (1972).
          8.  Estate of Powell, 148 T.C. 392 (2017).        10.  Smaldino, T.C. Memo. 2021-127.



         36  December 2022                                                                    The Tax Adviser
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