Rachel B. Oliver


Rachel B. Oliver focuses her practice on estate planning, probate and trust administration, and probate and trust controversies and litigation. Rachel brings a holistic and practical approach to estate planning and probate administration.  She helps high-net worth clients and their families to identify and understand their estate planning goals, and she advises them on the most efficient ways to achieve their goals, taking into consideration potential costs, family dynamics, and any potential estate, gift, or income tax issues.

St Pete Bar Association Logo
Florida Bar Real Property, Probate & Trust Law Section Logo

Prior Work Experience

Prior to joining The Diamond Law Firm, Rachel practiced with the national law firm of Cummings & Lockwood LLC in Naples, Florida, where she focused her practice on estate planning for high-net worth clients.  Rachel moved from Naples to St. Petersburg in 2016, where she married her husband, Reverend Andy Oliver, and became a step-mom to two boys, Liam and Evan. Upon moving to St. Petersburg, Rachel worked as a financial advisor with Merrill Lynch.  While at Merrill Lynch, she earned her Series 7 and Series 66 securities licenses, and her insurance license, and she assisted her clients with overall financial planning and investment management.*

*In her law practice, Rachel does not provide her clients with investment advice, financial advice, or other financial services.

Community Leadership

Rachel is a member of the local St. Petersburg Bar Association, the Real Property Probate and Trust Law Section of the Florida Bar, where she serves as a member of the Estate and Trust Tax Planning Council, and the Professional Partners Council of Suncoast Hospice.  She is also very active in her church, the social justice organization FAST (Faith and Action for Strength Together), and the League of Women Voters.

Articles and Publications

Avoiding Dissolution of Estate Plans in a Divorce, Collier County Bar Association’s “The Adverse Witness” (May/June 2014)

Disclose Before You Double-Dip the Chip, Collier County Bar Association’s “The Adverse Witness” (November 2014)

The Florida Guide to Prescription, Controlled Substance, & Pain Medicine Laws, Co-Authored with Alan S. Gassman with Gassman Law Associates, P.A., Lester Perling, with Broad and Cassel, and Dr. Pariksith Singh, M.D. (June 22, 2014)


Master of Laws in Taxation (LL.M.), University of Florida Levin College of Law, 2013

– Student Editor, Florida Tax Review

J.D., Stetson University College of Law, 2012

– Notes and Comments Editor, Stetson Law Review

B.S.W., Florida State University, 2008


(727) 823-1400
150 Second Avenue North, Suite 570
St.Petersburg, Florida 33701