David R Gray Jr.


A widely respected lawyer and a shrewd real estate investor, David R Gray, Jr. is the founder of The Law Offices of David R. Gray, Jr. Ltd., and is considered a leading expert in matters concerning real estate law, litigation, appeals and taxation. A longtime Chicago-area attorney, Mr. Gray also works with Wheeler Financial as its General Counsel, advising and representing the private investment firm on a wide range of legal issues. As an attorney, Mr. Gray has extensive experience in all facets of the law and has represented both defendants and plaintiffs in legal proceedings taking place in trial and appellate courts.

Formerly the Chairman of the Chicago Bar Association’s Real Estate Taxation Committee, Mr. Gray frequently contributes to the CLE programs made available through the bar association and has served as both a speaker and an author with the purpose of sharing his specific legal expertise with a broader audience. A member of both the Chicago Bar Association and the Illinois State Bar Association, Mr. Gray’s contributions to his field include co-authoring two of the chapters included in the Illinois Institute of Continuing Legal Education Real Estate Taxation Handbook. Mr. Gray was also featured as a seminar speaker at the IICLE Real Estate Taxation program hosted by the University of Chicago.

Mr. Gray earned his undergraduate degree from the College of Charleston, where he majored in philosophy with the intent of pursuing a career in the legal field. Upon graduation, Mr. Gray was accepted to the Valparaiso University School of Law, earning his juris doctorate and proceeding to begin his legal career in earnest. In addition to his lengthy and successful career as an attorney, Mr. Gray is also an accomplished real estate investor who has represented clients in closings for residential and commercial real estate properties along with a wide range of other transactional matters involving real estate.

  1. What was your best/favorite subject in school?

I thoroughly enjoyed the philosophy courses I took as an undergrad at the College of Charleston, and my favorite course was either my freshman-year ethics course or my senior seminar class on Nietzsche. I particularly enjoyed the book “Living high and letting die” by Peter Unger. That book has had a powerful effect on my life.

  1. What was your first job?

I had the distinct pleasure of working as a dishwasher at a Chicago-area restaurant. It turned out to be quite a valuable learning experience and I remain grateful for having that opportunity despite all of the hard work and late hours.

  1. Where and how did you first get into the industry you currently work in?

My father practiced law in Chicago for over 50 years, and it was his example that helped me decide that I wanted to pursue a career as an attorney.

  1. How have those jobs prepared you for what you do now?

One of the most important lessons regarding work in general came from my father, who told me that a person’s work ethic should not change according to the nature of the work they are doing. Every job is deserving of a consistently detail-oriented approach, which is the approach I have applied to my work in representing clients in legal matters.

  1. Describe the best day of work you’ve ever had.

Any day in which I am able to help achieve a favorable decision for a client feels like my best day of work, but I also felt a tremendous sense of personal pride on the day my private practice officially opened.

  1. How do you keep yourself motivated?

I understand how stressful any legal proceeding can be, so I understand just how critical my role is in representing a client and working to achieve the best possible outcome.

  1. What kind of business ideas excite you most?

I like to see business ideas that take advantage of a varied and unique personal skill set. My area of expertise is in real estate law, and I have been able to take advantage of the fact that I have specific expertise in both fields. This is one of the reasons I have become interested in the opportunities created by a number of developing concepts that others may not yet recognize.

  1. Have you ever tried any unorthodox techniques to attract attention to your business?

No, my reputation as an attorney tends to speak for itself. We use a limited amount of marketing and simply focus on serving our clients to the very best of our ability in all circumstances.

  1. What personal achievement are you most proud of?

While I have enjoyed a great deal of professional success as an attorney and a real estate investor, I am most proud of my supportive family.

  1. What wisdom you would have liked to share with yourself when you first started out?

The legal field can be incredibly draining for highly motivated individuals like me, so I would have advised myself to take a brief step back from work every once in a while just to make sure I maintained a sense of professional balance during those early years.