Robert L. Ostertag

1931 - 2021

Robert L. Ostertag

Poughkeepsie - Robert ("Bob") L. Ostertag, preeminent attorney, bar and community leader, died at home on July 15, 2021, at the age of 90. Up until a month before his death he was a participant in a purposeful and fulfilling life, having recently attended a bar association meeting via Zoom, a granddaughter's wedding reception, the Renegades opening day at Dutchess Stadium, a walking tour of Grand Central Station and enjoyed a few browses and lattes at Barnes & Noble. He then suffered a rapid decline while hospitalized from injuries due to a fall. Bob practiced law for 63 years until retiring at age 89 precipitated by the pandemic lockdown. He was born in Jamaica, Queens, on June 21, 1931, the son of Fred Charles Ostertag and Lillian Bishop Ostertag, both deceased by his age 20, leaving him alone in this world without parents or siblings. He nonetheless managed, by his intellect and perseverance, to live 70 more productive years, eventually revered for his substantial contributions to the profession he loved and to his community.

Bob received a BA degree from Fordham University in 1953, his LL.B. from St. John's University School of Law in 1956 and went on to receive an LL.M. from Georgetown University Law Center in 1960. Directly after law school he served to rank of Captain in the US Air Force in the Judge Advocate General Corps stationed at Dow AFB in Maine. There he quickly developed his skills as a trial lawyer and gained admission to the U.S. Court of Military Appeals. After the honorable discharge of his military obligation, he accepted a position as Assistant Chief Counsel at the IRS, Alcohol & Tobacco Tax Division, Washington, DC. He simultaneously received his masters in taxation and estate planning, adding to his developing legal knowledge and skills, and was admitted to the U.S. Tax Court. (In later years he listed as one of his proudest accomplishments a litigation memorandum he authored which passed through all channels up to the White House with only 2 minor changes, neither substantive.)

In 1960 Bob accepted a position with the prominent local law firm of Guernsey Butts & Walsh, proudly attaining partnership status within 3 ½ years. He remained in private practice in Dutchess County for the remainder of his career, continuing as a member of Guernsey Butts Ostertag & O'Leary and other iterations, his last as a member of the law firm of Ostertag O'Leary Barrett & Faulkner.

Bob was a "lawyer's lawyer"; his colleagues often sought his counsel as well as his representation. The practice of law was never about money. He gave every client 100%, often without full remuneration. With private practice came a lifelong commitment to the organized bar as well as service to his community. Bob served the Dutchess County Bar Association (DCBA) not only as its President in 1984-85 but oversaw its operation as Secretary-Treasurer for 10 years before the association hired an executive director. He spent from the late 1970's to his death active in the New York State Bar Association (NYSBA) chairing committees and holding executive positions eventually leading to his being elected President by his peers for the term 1991-92, the pinnacle of his career of which he was most proud. Throughout his involvement in the NYSBA he was a dogged champion for all the solo and small firm practitioners in the many small towns in NY who often struggle to make a living, making sure they had a strong advocate in their bar association and a seat at the table when important decisions were to be made. He was responsible for 2 publications designed to address the needs of those attorneys, as Chairman of the Editorial Board producing the New York Lawyers Deskbook, NY State Bar Ass'n 1989, and as Co-Editor, General Practice in New York (6 Volumes), West Group 1998, the latter a labor that took up his "free time" for almost 2 years. He was also active in the ABA, chairing and serving on various committees and as a NY State Delegate. In his later years he took pleasure in serving on its Gavel Awards Committee, reading and rating newly published books on the law, an annual service he performed up to just months before his death. He relished sharing his knowledge of the law and his practical wisdom with anyone seeking to enter the legal profession. Bob was an Adjunct Professor of Wills, Estates & Trusts from 1976-91 in the Marist College Paralegal Program and an Adjunct Professor of NY Civil Practice at Fordham University School of Law from 1990-2007. He continuously served on the Marist College Paralegal Advisory Board since its inception and 10 years on the Pace University School of Law Advisory Council. He was honored with many special recognitions and numerous awards for service to his profession, including two Lifetime Achievement Awards in 2004, from the NYSBA and the ABA, respectively, and a special recognition dinner given by the Dutchess County Bar Association in 2014. Bob was a recipient of the Marist College President's Award for service to the people of the Hudson Valley in 1991 and the Dutchess County Bar Association's Jack Gartland Community Service Award in 2010.

Bob always sought involvement in some community service, the list being too long to include. In recent years he particularly enjoyed his service as director and then chairman of the Hudson Valley Stadium Corporation. He served on the board of the Arlington Business Improvement District. Recalling his earlier years, he was proud of his work as counsel to consult and draft county charters and administrative codes for several counties. He took pride in his authorship of Dutchess County's governing charter (1966-67) which changed its government after a half century and remains as written by him but for updates on new departments and agencies. He served on and chaired numerous boards of directors, to name only a few: Standard Gage Co., the Dutchess County Board of Health, Sports Museum of Dutchess County, the American Heart Association and, related to his lifelong love of music, the High Tor Opera Co. and the Hudson Valley Philharmonic Society.

Bob cherished his families, biological and extended, his office family and his NYSBA family. He nurtured friendships, even remaining in touch with friends from his grammar school, St. Ann's Academy in NY City, until one by one they predeceased him.

Bob was a man of many talents and interests. He was a voracious reader, a student of history and politics, a lover of travel and a music lover who played his Steinway every day with passion. A sports fan, he enjoyed season tickets to the NY Rangers and NY Giants with his friends. Most of all, he loved the game of baseball, the Brooklyn Dodgers and then his beloved Mets, having attended 56 consecutive Mets openings days. He was a lifelong Democrat to his core.

He leaves behind Diane O'Leary, honored and blessed to have been his law partner for over 30 years and his life partner for almost as many. He leaves his children with his former wife Ann (deceased), with pride in their accomplishments and those of their children, gratified that many of them share some of his passions: his son Thomas Ostertag and wife, Judith Russell, of Scarsdale, NY; his son Daniel Ostertag and wife, Patricia, of Tewksbury, MA; his daughter Debra Wall and husband Scott of Poughkeepsie; and, his grandchildren, Emily Ostertag Whittle and husband TJ of Arlington, VA; Elizabeth Ostertag of NY,NY ; John Ostertag of Scarsdale, N Y; Meghan Ostertag of Tewksbury, MA; Madison Wall of Poughkeepsie; April Cluess of Tallahassee, FL; Christopher Cluess of Beacon. He leaves his office family, which over the past 26 years expanded from his partnership with Diane to include his partners Maura Barrett and Sharon Faulkner. He leaves his extended family who loved and embraced him as their own and he them: Sharon (O'Leary) Faulkner and husband David of Poughkeepsie and their sons, Riley and Rowan; Brian O'Leary and wife Lynley Chandler O'Leary of Red Hook and Brian's daughters, Cullen and Aubrey, as well as all others in Diane's family.

Bob was known for his dry wit, humility, dignity and grace in addition to his superior legal ability and ethical standards. Over his waning years he continually expressed gratitude for any good fortune that came his way and for his long life and good health. He often said he did not know how he deserved to be so fortunate. His was a life well-lived. He will be missed by many.

In lieu of flowers please consider a memorial donation to the New York Bar Foundation, General Fund, through its website or via mail to 1 Elk Street, Albany, NY 12207.

Calling hours with the family will take place at Wm. G. Miller and Son Funeral Home, Inc.371 Hooker Avenue, Poughkeepsie, NY 12603, on Friday, July 30, 2021, from 4:00 p.m. to 7:00 p.m. If you wish to send an online condolence please visit our website at www.wmgmillerfuneralhome.com