Our Practice

Practice Areas

We  provide legal services in the following practice areas:   


  • Estate Planning and Administration
  • Business Planning
  • Tax
  • ERISA and Executive Compensation 
  • ESOPs

Our Approach

Our focus is on you, the Client.  We know that communication is one of the most important aspects of our relationship, so we will do our best to keep you informed.  We are dedicated to understanding what results you want and helping you understand what actions can be taken to obtain those results.  Our goal is to provide quality legal services at a fair price.  

Legacy of Success

Mr. O'Leary, founder of David  O'Leary Law,  recently retired from Holland & Knight, LLP.  He has been practicing  law for more than 40  years, servicing both small and large clients in all types of personal and business matters.   He has a proven track record of success and the knowledge and experience to help you obtain the results you want.  

David O'Leary

Mr. O'Leary has over 40 years' experience advising clients on innovative and cost-effective ways of planning and solving problems with respect to ESOPs, ERISA, executive compensation, taxation, family business, and estate planning issues.  


  • ESOPs. There are many parties to an ESOP transaction.  Whether you are  a company wanting to adopt an ESOP, a selling shareholder wanting to sell stock to the ESOP, a bank wanting to loan money to finance the ESOP transaction, or the ESOP trustee acting on behalf of the ESOP, Mr. O'Leary has the knowledge and expertise to advise you. He has been involved in all facets of the ESOP cycle and was the co-chairman of the ESOP Team at Holland & Knight, LLP.
  • Executive Compensation and ERISA.  Mr. O'Leary has had significant experience with all types of benefit plans,  including  401(k) and other qualified plans,  nonqualifed deferred compensation plans, and equity-based incentive arrangements.  He is very knowledgeable of ERISA fiduciary liability issues, plan asset rules, avoidance of prohibited transactions and multiemployer pension plan withdrawal issues.   He provides clients with creative and practical solutions to all types of ERISA issues.  He is past chairman of the Chicago Bar Association Employee Benefits Committee.
  • Tax and Estate Planning,  Mr. O'Leary is well versed in the latest developments in the tax and estate planning areas.  He is very familiar with the various types of business entities, including corporations, partnerships and limited liability companies.  He has considerable experience crafting business ownership succession plans to facilitate tax-efficient transfers of business ownership.  He is also experienced in estate planning techniques and the administration of complex estates and trusts.  
  • Bar Admissions
    • Illinois
    • Florida
  • Certified Public Accountant 
  • Illinois Leading Lawyer for 2018