David B. Shiner

David B. Shiner
Practice Areas

Corporate Transactions & Business Law
Estate & Trust Administration & Litigation
Estate Planning & Asset Protection
Not for Profit & Mission-Based Organizations
Tax & Employee Benefits


IIT Chicago-Kent College of Law, LL.M. Taxation (2001)

The John Marshall Law School, J.D. (1996)

Illinois CPA (1995)

Boston University, B.S.B.A. (1992)

Bar & Court Admissions

Illinois (1996)

U.S. District Court, Northern District of Illinois (1996)

U.S. Tax Court (2004)

U.S. Court of Federal Claims (2007)



David Shiner regularly deals with the IRS on tax controversy matters and doesn’t back down from taking cases to trial when necessary. "We're going to fight to get the best result for our client."

David Shiner, a Principal with Chuhak & Tecson, is a business and tax attorney focusing his practice in estate planning, taxation and corporate law. He leads the firm's tax and employee benefits practice group.

A certified public accountant with a master of laws in taxation, David is uniquely qualified to counsel his clients on structuring transactions, such as domestic and foreign asset protection trusts, to reduce the risk of exposure to potential creditors, as well as minimizing exposure to federal and state estate taxes, such as by using grantor trusts, grantor retained annuity trusts (GRAT), qualified personal residence trusts (QPRT), irrevocable life insurance trusts (ILIT), charitable lead annuity trusts (CLT) and charitable remainder trusts (CRT).

David also battles the IRS both in administrative proceedings and in U.S. Tax Court in gift, estate and income tax matters where hundreds of thousands to a million dollars of taxes are assessed.

Some of his notable cases include the following:

  • SAS Investment Partners v. Commissioner, T.C. Memo 2012-159, whether reasonable cause existed to abate penalties in "Son of Boss" tax shelter.
  • Estate of Dorman v. Commissioner, Docket No. 11884-11 (settled June 2013), valuation of closely held business for purposes of estate tax.
  • Todd v. Commissioner, T.C. Memo 2011-123, whether loan from welfare benefit fund was a part of a tax shelter and constituted income.
  • Tomkinson v. Commissioner, Docket No. 14136-09, whether taxpayer was entitled to charitable deduction for donation of façade easement on residence. (Settled March 2010).
  • Mulcahy, Pauritsch, Salvador & Co, Ltd v. Commissioner, T.C. Memo 2011-74, whether payments to employee-shareholders constituted reasonable compensation. 
  • 3K Investment Partners v. Commissioner, 133 T.C No. 6 (2009), whether taxpayer could compel discovery of a list of all tax opinion letters collected by the IRS regarding “Son of Boss” tax shelters to establish the existence of reasonable cause. (Settled December 2009 after partial abatement of penalties).
  • Paschen v. Commissioner, Docket No. 17865-06, whether restitution of embezzled funds created net operating losses and whether wife was entitled to innocent spouse relief. (Settled December 2009).
  • Estate of Ziegler v. Commissioner, Docket No. 25060-06, effect of botched estate planning strategy on estate tax including valuation issues. (Settled July 2009).
  • Smith v. Commissioner, Docket No. 1133-08, whether shareholder loans constituted income, whether losses were subject to passive activity rules and whether costs for repairs should be expensed or capitalized. (Settled July 2009).
  • Murphy v. Commissioner, 129 T.C. 82 (2007), whether mailing of an FPAA to a beneficiary rather than to his trust satisfied the notice requirements of IRC §6223(a).
  • Nichols v. Commissioner, T.C. Memo 2007-5, whether Tax Court had jurisdiction to review taxpayer’s net operating loss deduction where taxpayer previously executed an IRS waiver.

David is a member of Chuhak & Tecson's Management Committee and previously served on the Finance Committee.