Member Spotlight: Robert L. Ostertag

By Robert L. Ostertag

Tell us a little bit about your career.

  • Ass't Staff Judge Advocate, USAF, Dow Air Force Base, Maine,
  • Ass't Chief Counsel, IRS Alcohol & Tobacco Tax Division, Washington, DC,
  • Private practice:  Guernsey Butts & Walsh, Poughkeepsie, NY, 36 years, litigation, taxation & estate planning & administration,
  • Ostertag O'Leary Barrett & Faulkner, Poughkeepsie, NY  21 years, litigation, taxation, estate planning & administration.

Is it what I had planned when I started law school?

 Not exactly.

What has been the highlight of your career?

There are several, which include:

  • Presidency of the local and New York State Bar Association, selected by election of my peers,
  • Authorship on behalf of U.S. Treasury and Justice Departments of a first time 30 +/- page litigation memorandum on the then-constitutional status of the Commonwealth of Puerto Rico which passed through the IRS, the Treasury Dept., the State Dept. and the White House with but two changes, one political, the other grammatical,
  • Brief service as counsel to the NYS Legislature's Agriculture Committee,
  • Authorship of my county's governing charter that changed its form of government which, after more than a half century, still stands as its local constitution as written but for updates and additions of new departments and agencies, and
  • Various litigation verdicts and decisions.

If you could go back to the beginning of your legal career, would you have done anything differently?

Perhaps I'd have stayed in the Air Force with a bright future predicted for me, and also in the IRS Chief Counsel's Office, also with a very bright future predicted for me, but at the time I wanted to see if I could make it in private practice.

What advice would you give to someone considering law school today?

To think very carefully about it. It's tough, life-consuming if done right, impedes heavily upon one's private life, and leads frequently to destructive personal choices. On the other hand, it is tremendously intellectually rewarding and of important service to many people. It provides an opportunity to do a life's work that other people cannot.

But if you think you can gain wealth from it, think again unless you are fortunate to find a white shoe opportunity, and such opportunities are highly competitive starting the first day of law school. One must learn to love the law and its magnificent intellectual intricacies.  Many, if not most people, cannot. 

Depending upon the audience, I might mention the old adage about lawyers dying younger, becoming alcoholics more frequently, messing up their private lives more often, and all those other wonderful things we lawyers learn too late in life. What was it that Arthur Godfrey used to say, "Too soon old and too late schmart?” But if you think you can absorb all that and want to meet some of the finest people on God's earth, then think about it.

What were the biggest changes you saw in the legal profession over the course of your career?

Technology, bar none.  Just think how solo and small firm practitioners (I call them "SoSmalls") can now take on downtown Manhattan white shoes. On the other hand, technology is one  major pain in the a**.

When did you first become a member of the ABA and why did you decide to join?

While in law school. If you really wanted to be a lawyer, it was the thing to do.

What has been the highlight of your work with the ABA?

Involvement with so many terrific people from all over the country. It's always about the people.

If you had not become a lawyer, what do you think you would have done?

My first desire to be something was to be a garbage man. I thought hanging off the side of one of those big trucks was pretty cool. Then a NYC bus driver. Then a ball player—oh well. I might have become a commercial pilot―had I learned to fly in the Air Force. Then a journalist―how I'd have loved to write weekly columns for the Hopewell Junction Gazette about the excitement downtown. But, in retrospect, I'd still probably enjoy hanging off the truck. Initial instincts are usually the best. And they have handles these days. 


Robert L. Ostertag is a past President of the New York State Bar Association and JAG attorney, Mr. Ostertag is a veteran trial lawyer with over 50 years of experience. He serves on several statewide and nationwide committees. He resides in Poughkeepsie, New York.