Howard J. Castleman, a member of the Private Wealth Services Group based in the Boston office, concentrates his practice in fiduciary and probate litigation, tax controversies and disputes involving closely held companies. A seasoned trial attorney, Mr. Castleman has won a number of high-profile cases involving fiduciary litigation, tax matters and family businesses, and also serves as a trusted advisor to individuals and institutional clients.
Prior to starting private practice, Mr. Castleman served as law clerk to the Honorable Ronald Lagueux of the U.S. District Court for the District of Rhode Island.
Mr. Castleman has also chaired national and regional conferences on controlling litigation costs through improved client collaboration, effective use of technology, strategic budgets and alternative fee arrangements. He has lectured at Massachusetts Continuing Legal Education (MCLE) engagements and served on MCLE's civil curriculum advisory committee.
Representative cases include:
winning, on behalf of a decedent's estate, an unprecedented federal gift tax case, establishing at trial 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
successfully 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
successfully representing a trustee seeking to remove a co-fiduciary for breach of fiduciary duty, negligence and conflict of interests, leading to the appointment of a successor co-fiduciary
winning, through partial summary judgment and then trial, judgment for a defendant accused of breaching fiduciary duties arising out of the transfer of his shares in a substantial family business to trusts for his children
successfully representing a 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
successfully representing the defendant, an accountant and a certified public accounting (CPA) 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
representing a defendant 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
