representative cases

Complex Business Litigation and Fiduciary Disputes

Among Howard Castleman's notable representations are the following:

·       Winning at trial, on behalf of decedent's estate, an unprecedented federal gift tax case, establishing that the estate did not owe approximately $20 million in gift tax, interest and penalties arising out of the settlement of litigation concerning ownership of a family business, which had taken place 40 years earlier, Estate of Edward Redstone v. Commissioner, 145 T.C. No. 11, October 26, 2015;

·       Representing landowner in a family dispute involving 1,700 acres of land in Monterey, Calif., including the development of 300 acres for mixed-use, including residential, commercial and industrial uses with an estimated assessed value of $1.1 billion.  Armstrong Sandhill Ranch LLC v. Murray, Monterey County Superior Court, Case No.  M131455 (2016);

·       Representing co-trustee and beneficiaries of family trust, in removal of co-trustee accused of breach of fiduciary duties and misappropriation of trust assets; 

·       Representing taxpayer, the owner of a large portfolio of multifamily housing, in a multimillion-dollar federal tax controversy regarding a challenge to the Internal Revenue Services' (IRS) characterization of the taxpayer's rental real estate activities as subject to the passive loss limitations of Section 469 of the Internal Revenue Code;

·       Representing trustees in a challenge by a beneficiary to a prior trustee's valuation of inter vivos gifts, where the trust instrument called for the equalization of trust shares based on past gifts;

·       Representing defendants, a certified public accountant and his accounting firm, in a $1.4 million professional malpractice action alleging negligence in the establishment of an employee stock ownership plan (ESOP) and fraud in an alleged cover-up with the IRS;

·       Winning at trial and on appeal judgment for defendant trustee accused of breaching fiduciary duties arising out of transfer of shares in a multi-billion dollar holding company to trusts for his children.  O'Connor v. Redstone, 452 Mass. 537 (2008).