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Massachusetts Lawyers Weekly article, “‘No contest’ clause not grounds to dismiss beneficiary’s challenge to trust,” quotes Howard J. Castleman

Massachusetts Lawyers Weekly


An “in terrorem” clause in a family trust document did not automatically bar a beneficiary from suing a trustee for  alleged undue influence over the grantor in establishing the trust, a Superior Court judge has ruled.  

An in terrorem clause — also called a no-contest clause — is a provision in an estate document that disinherits anyone who challenges its terms.  The defendant trustee argued that by bringing the lawsuit the plaintiff beneficiary automatically became a non-beneficiary under the no-contest clause, leaving her without standing to assert her claims.

But Judge Edward P. Leibensperger, sitting in the Business Litigation Session, disagreed.  He ruled that a no-contest clause in trust does not prevent a beneficiary from bringing a lawsuit challenging the trust.  If the contest is successful, the no-contest clause falls with the rest of the instrument, the judge ruled. 

Castleman Law partner Howard Castleman said the Court correctly rejected the defendants’ argument which, on a motion to dismiss, would have deprived plaintiffs of even the opportunity to prove the alleged undue influence.  Castleman added, “In so ruling, Judge Leibensperger preserved the plaintiffs’ ability to have their day in court while announcing an important limitation on the operation of no-contest clause provisions in the Commonwealth.“  

To read the full article, please click here


Estate of Edward Redstone Wins Challenge to IRS Tax Claim on Alleged Gift Dating Back to 1972, November 4, 2015

Howard Castleman of Castleman Law LLC, leading a team of lawyers from Boston area law firms, achieved a significant victory in an unprecedented federal gift tax case on behalf of the Estate of Edward Redstone, the deceased younger brother of media mogul Sumner Redstone.  

On October 26, 2015, the United States Tax Court issued its 31-page opinion in Estate of Edward Redstone v. Commissioner, 145 T.C. No. 11 (October 26, 2015).  The Tax Court held that Edward’s estate owed no gift tax arising out of the 1972 settlement between Edward, his brother Sumner, and their father Mickey Redstone.  The IRS had sought over $1.1 million in tax deficiencies and penalties -- and over 40 years of interest -- from the Estate of Edward Redstone, who died in 2011.

Attorney Castleman described the Tax Court opinion as “well-reasoned and thorough.”  Castleman added, “What is extraordinary is that, after more than 40 years, the IRS alleged that Edward Redstone’s compromise of a bitter family dispute was a “sham” to avoid gift tax where, as the Tax Court held, ‘All evidence points in the opposite direction.’”

The Tax Court's opinion is reported as Estate of Edward Redstone v. Commissioner, 145 T.C. No. 11 (2015).

The decision was widely reported, including in Tax Notes Today.  To read the press release, please click here.


Speaking Engagements


On February 7, 2018, Howard Castleman of Castleman Law LLC spoke at a BBA program addressing issues Trustees face when hiring and paying for legal counsel.  The program was entitled, "Touchy Topics of Engaging Counsel, the Privilege of Privilege, and Who Pays the Bill?"  Howard joined co-speakers, Susan Robb (First Republic Trust Company), Elizabeth Connelly (Boston Private Bank & Trust Co.) and Ryan McManus (Hemenway & Barnes LLP).  The program was jointly sponsored by the following BBA Sections/Committees:  Trusts & Estates Section, Trust Administration Committee, Fiduciary Litigation Committee, In-House Lawyers Forum.

Wednesday, February 7, 2018 12:30 PM to 1:30 PM
Boston Bar Association - 16 Beacon Street, Boston, MA

For more information, please click here