About us

OUR TEAM

J. Richard Caskey (“Rich”), a Tampa native, focuses his law practice in the areas of estate and trust litigation, fiduciary liability, and probate law.  Rich assists families and fiduciaries in various aspects of estate, trust, and guardianship administration, and handles all aspects of disputes that might arise in those matters, including litigation, mediation, and trial. 

 

Download CV (PDF)

Admissions & Certifications

  • Admitted to The Florida Bar and all Florida State Courts
  • Admitted to United States District Court, Middle District of Florida
  • Florida Supreme Court Certified Circuit Mediator
  • Florida Supreme Court Certified Appellate Mediator
  • Florida Qualified Court Appointed Arbitrator
  • Fellow of the American College of Trust and Estate Counsel (ACTEC)

Bar Association Activities

 

The Florida Bar Real Property, Probate & Trust Law (RPPTL) Section

  • Probate and Trust Litigation Committee (Chair 2018 – present; Vice Chair 2011 – 18)
  • Probate Law and Procedure Committee (Member 2005 – Present)
  • Executive Council (2007 – Present)
  • ActionLine magazine (past Editor-in-Chief) (Substantive legal publication for the RPPTL

Section with quarterly circulation of approximately 10,000)

 

The Florida Bar

  • Code and Rules of Evidence Committee (2018-present)
    • Liaison to Probate Rules Committee
  • Probate Rules Committee (2009 – 2015)
    • Vice-Chair (2011 – 2012; 2013 – 2015)
    • Liaison to RPPTL Probate Law and Procedure Committee (2009 – 2011)
  • Rules of Judicial Administration Committee
    • Liaison Sub-Committee, Vice-Chair (2012 – 2015)
    • Liaison to Probate Rules Committee (2011 – 2015)

 

Hillsborough County Bar Association (HCBA)

  • HCBA Leadership Institute (Executive Committee 2008-09)
  • Real Property, Probate & Trust Law Section (Chair 2005-07)

Awards & Recognition

 

Selected as one of only four lawyers in the state of Florida for the 2009 Florida Super Lawyers inaugural “Rising Stars” list in the area of Estate and Trust Litigation.  Repeatedly selected as a “Super Lawyer” in the area of Estate and Trust Litigation.

 

Repeatedly selected by Florida Trend magazine as a member of the “Florida Legal Elite” list.

 

Repeatedly selected by The Best Lawyers in America in the area of trusts and estates litigation.

 

Awarded the James M. “Red” McEwen Memorial Award for outstanding service to the Hillsborough County Bar Association.

 

Rated AV Preeminent, Martindale-Hubbell.

Articles & Publications

 

Florida Guardianship Practice, Chapter 6, “Use of Joint Assets”

(The Florida Bar 7th ed. 2011; 8th ed. 2014; 9th ed. 2016; 10th ed. 2018)

 

“Alleging Undue Influence:  Maybe You Don’t Have to Be So Presumptuous”

– The Florida Bar RPPTL ActionLine magazine, Spring 2010

 

“Homestead and Pay-on-Death Accounts: Two Completely Unrelated Cases of Interest”

– The Florida Bar RPPTL ActionLine magazine, Spring 2009

 

“Protecting the Homestead; Protecting the Public: Waiver of homestead exemption from forced sale is unenforceable.”

– HCBA Lawyer magazine, May 2008

 

“Second District Court of Appeal Upholds Constitutionality of Elective Share”

– The Florida Bar RPPTL ActionLine magazine, Spring 2008

 

“In Search of the Laughing Heir”

– HCBA Lawyer magazine, June 2007

 

“Looking for the Laughing Heir: Potential Expansion of Intestate Succession Laws”

– The Florida Bar RPPTL ActionLine magazine, Summer 2007 

 

“Changes in the Law Regarding Revocable Trusts”

– HCBA Lawyer magazine, October 2006

 

“Homestead and Amendment 10: Don’t Let the ‘Cap’ Out of the Bag”

– HCBA Lawyer magazine, April 2006

 

“Equitable Adoption: Setting Things Right”

– HCBA Lawyer magazine, November 2005

 

“Reformation of an Unambiguous Trust Instrument”

– HCBA Lawyer magazine, September 2005

Speaking Engagements, Lectures & Seminar Presentations

 

“Lost and Found: Litigating Lost and Later-Discovered Wills”
Estate Trust and Guardianship Seminar
Orange County Bar Association; Continuing Legal Education
Remote Presentation, February 12, 2021

 

“Best Practices for Remote Mediations”
Hillsborough County Bar Association RPPTL Section; Continuing Legal Education
Featured Speaker, Remote Presentation, January 14, 2021

 

“Estate Mediations in the Remote Era”
Dade County Bar Association, Probate and Guardianship Committee
Featured Speaker, Remote Presentation, October 13, 2020

 

“Making the Most of Mediation in Estate Disputes”
Orange County Bar Association; Continuing Legal Education
Featured Speaker, Orlando, FL, May 11, 2020

 

“Virtual Mediation During the Pandemic”

The Florida Bar Real Property Probate and Trust Law Section

Webinar (rpptl.org) April 3, 2020

 

“Staying out of Trouble!”

Professional Fiduciary Council of Florida

Panel Member, St. Petersburg, Florida, February 6, 2020

 

“Top 10 Issues in Estate and Trust Mediations”

     St. Petersburg Bar Association; Continuing Legal Education

Featured Speaker, St. Petersburg FL, December 10, 2019

 

“Probate and Trust Professionals Panel”

Bench and Bar CLE

Clearwater and St. Petersburg Bar Association; Continuing Legal Education

Panel Member, Gulfport, Florida, November 15, 2019

 

“Expert Evidence – Admission, Ethics and the Daubert/Frye Conundrum”

Hot Topics in Evidence 2019

The Florida Bar; Continuing Legal Education

Co-Speaker, Orlando, FL, June 7, 2019

 

“Mediation in Trust and Estate Matters”

Hillsborough County Bar Association RPPTL Section; Continuing Legal Education

Featured Speaker, Tampa, FL, May 9, 2019

 

“Expert Witnesses – When You Can Use Them and How”

2019 Litigation and Trust Law Symposium

The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education

Co-Speaker, Ft. Lauderdale, FL, March 29, 2019

 

“What Every Planning Professional Should Know about Undue Influence”

Gulf Coast Estate Planning Council

Featured Speaker Trinity, FL, January 15, 2019

 

“Case Law Update”

Probate Law 2018

The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education

Tampa, FL, November 2, 2018

 

“Where Guardianship and Trust Law Intersect”

Orange County Bar Estate, Guardianship and Trust Seminar

Orange County Bar Association; Continuing Legal Education

Panel Member Orlando, FL, October 12, 2018

 

“Pitfalls of the Personal Representative: Powers and Duties”

Collier County Bar Association Trusts and Estates Symposium

Collier County Bar Association; Continuing Legal Education

Naples, FL March 23, 2018

 

“It’s off to Court We Go – Guardianship Power over Trusts”

RPPTL Litigation and Trust Law Symposium 2018

The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education

Co-Program Chair and Panel Member Tampa, FL, March 2, 2018

 

“Probate Power Hour – New Cases and Statutes”

The Probate Team

Florida Legal Education Association (FLEA); Continuing Legal Education

Orlando, FL October 20-21, 2017

 

“Guardianship Authority over Trusts”

RPPTL Guardianship Seminar 2017

The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education

Miami Gardens, FL, April 28, 2017

 

“Mediation Issues in Guardianship”

Hillsborough County Bar Association Elder Law Section; Continuing Legal Education

Featured Speaker, Tampa, FL, January 20, 2017

 

“Probate Rules Update”

Hillsborough County Bar Association Real Property, Probate & Trust Law Section

Featured Speaker, Tampa, FL, November 17, 2016

 

“Fiduciary Liability and Elder Exploitation Claims”

     Opening the Chamber of Secrets: What You Need to Know for Your Estate Planning Practice

Orange County Bar Association; Continuing Legal Education

Orlando, FL, October 14, 2016

 

“Elder Exploitation Issues for the Fiduciary”

     St. Petersburg Bar Association; Continuing Legal Education

Featured Speaker, St. Petersburg FL, April 12, 2016

 

“Current Issues for Elder Exploitation”

Hillsborough County Bar Association Elder Law Section; Continuing Legal Education

Featured Speaker, Tampa, FL, April 8, 2016

 

“Elder Abuse Issues (and Traps) for the Fiduciary”

2016 Litigation and Trust Law Symposium

The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education

Tampa, FL, March 4, 2016

 

“Guardianship and Probate Mediation”

2015 UnProgram

Academy of Florida Elder Law Attorneys; Continuing Legal Education

Facilitator, Orlando, FL, December 5, 2015

 

“Avoiding Litigation in Probate”

Suncoast Estate Planning Council

Featured Speaker, St. Petersburg, FL, December 3, 2015

 

“Expansion of Standing to Protect Assets of the Elderly”

Hillsborough County F.A.S.T. Task Force

Featured Speaker, Tampa, FL, May 6, 2015

 

“Fulfilling Duties: A Guide to Counsel for the Personal Representative”

Probate Law 2014 Seminar

The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education

Tampa, FL, December 12, 2014

 

Probate – A View from the Bench”

18th Annual Bench/Bar Conference

Hillsborough County Bar Association

Moderator, Tampa, FL, October 30, 2014

 

“Undue Influence?  Prove it!”

The Probate Team

Florida Legal Education Association (FLEA); Continuing Legal Education

Orlando, FL October 10-11, 2014

 

“Exploitation of Vulnerable Adults – Protecting the Assets of the Elderly”

Hillsborough County Bar Association Real Property, Probate & Trust Law Section

Featured Speaker, Tampa, FL, October 9, 2014

 

“Avoiding Litigation in Probate”

Hillsborough County Bar Association Real Property, Probate & Trust Law Section

Featured Speaker, Tampa, FL, November 14, 2013

 

“Will Contests and Probate Litigation”

Stetson University College of Law

Guest Lecturer, Gulfport, FL, March 5, 2013

 

“Homestead Law Update”

Hillsborough County Bar Association Real Property, Probate & Trust Law Section

Featured Speaker, Tampa, FL, November 8, 2012

 

“Marital Agreements: Inheritance and Other Rights of a Surviving Spouse”

Collaborative Divorce Institute of Tampa Bay

Featured Speaker, Tampa, FL, June 13, 2012

 

“Professional Practice and Conflicts in Estate Planning”

Venice Estate Planning Council

Featured Speaker, Venice, FL, May 14, 2012

 

“I’m No Carpenter – Litigating Undue Influence without the Presumption”

Litigation and Trust Law Symposium 2012

The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education

Ft. Lauderdale, FL, May 10, 2012

Tampa, FL, May 11, 2012

 

“Adversary Proceedings in Probate”

The Florida Bar Elder Law Section, Probate Committee

Featured Speaker, May 8, 2012

 

“Probate Law 2012”

The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education

Program Chair, Ft. Lauderdale, FL, March 22, 2012

 

Nuts and Bolts of Probate, Trust, and Guardianship Practice”

15th Annual Bench/Bar Conference

Hillsborough County Bar Association

Speaker, Tampa, FL, November 17, 2011

 

“Rules of Judicial Administration Update”

Plant City Bar Association; Continuing Legal Education

Featured Speaker, Plant City, FL, April 8, 2011

 

“Use of Rules of Civil Procedure in Probate”

Rules, Deadlines, and Essential Issues and Developments in Probate Practice

The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education

Program Chair and Speaker

Tampa, FL, March 17, 2011

Ft. Lauderdale, FL, March 18, 2011

 

“Alleging Undue Influence: Maybe You Don’t Have to Be So Presumptuous”

Hillsborough County Bar Association Real Property, Probate & Trust Law Section

Featured Speaker, Tampa, FL, March 10, 2011

 

“Alleging Undue Influence”

Sarasota Bar Association; Continuing Legal Education

Featured Speaker, Sarasota, FL, January 26, 2011

 

Issues of Judicial Concern in Probate, Trust, and Guardianship Proceedings”

14th Annual Bench/Bar Conference

Hillsborough County Bar Association

Moderator, Tampa, FL, November 16, 2010

 

“It’s My Indispensable Party and I’ll Die If I Want To: Jurisdiction, Notice, and Interested Parties Under the Probate Code”

When Good Estates Go Bad: Dealing with Unexpected Issues in Probate

The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education

Tampa, FL, March 25, 2010

Ft. Lauderdale, FL, March 26, 2010

 

“Redistributing the Wealth: Obtaining Attorneys’ Fees in Estate and Trust Matters”

Trust and Estate Stimulus Package: Shovel-Ready Issues for Planners and Litigators

The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education

Ft. Lauderdale, FL, February 10, 2010

Tampa, FL, February 11, 2010

 

“Hip-Hopping on Adoption and Paternity Issues”

So You Think You Can Dance…But Can You Do the Probate Shuffle?

The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education

Ft. Lauderdale, FL, March 19, 2009

Tampa, FL, March 20, 2009

 

“The Least Restrictive Alternative”

The Guardianship Team

Florida Legal Education Association (FLEA); Continuing Legal Education

Tampa, FL February 20-21, 2009

 

“Avoiding Legal Arthritis: Treatment of ‘Joint’ Issues”

2009 Estate and Trust Symposium:

The Best Laid Plans … A Showdown Between the Drafters and the Litigators

The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education

Co-Speaker, Tampa, FL, February 12, 2009

Speaker, Ft. Lauderdale, FL, February 13, 2009

 

“Conflicts of Interests in Estate and Trust Matters”

     St. Petersburg Bar Association; Continuing Legal Education

Featured Speaker, St. Petersburg FL, November 20, 2008

 

“The Prudent Practitioner: Avoiding Conflicts of Interests in Estate and Trust Matters”

     Clearwater Bar Association; Luncheon CLE Series

    Featured Speaker, Clearwater, FL, October 16, 2008

 

“Various Conflicts of Interests that Might Arise in Estate and Trust Matters”

Estate, Trust and Tax Issues at Their Best!

Hillsborough County Bar Association; Continuing Legal Education

Tampa, FL, October 14, 2008

 

“Rules of Professional Conduct and Conflicts of Interests”

Hillsborough County Bar Association Real Property, Probate & Trust Law Section

Featured Speaker, Tampa, FL, March 13, 2008 

 

“Who’s in Charge?: Liability Issues and Concerns for Directed Trustees”

Your 2008 Estate and Trust Symposium:  Litigating Under the New Florida Trust Code

The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education

Ft. Lauderdale, FL, February 7, 2008

Tampa, FL, February 8, 2008

 

“The Creative Undue Influencer:  Challenging Marriage in Probate”

Hillsborough County Bar Association Real Property, Probate & Trust Law Section

Featured Speaker, Tampa, FL, September 13, 2007

 

Law Student Forum

The Florida Bar Real Property, Probate & Trust Law Section

Panel Member, Gulfport, FL 2004

Panel Member, Gainesville, FL 2002 

 

Law School Symposium

Phi Alpha Delta

Keynote Speaker, Gainesville, FL 1999; 2000; 2001; 2002

Education

 

2001 Juris Doctor (J.D.), With Honors, University of Florida College of Law

Book Award in Mediation Clinic

Book Award in Trial Practice

Book Award in Income Taxation

 

2000 Master of Business Administration (M.B.A.), University of Florida

– Dual concentrations in Finance and Management

– Poe Ethics Fellowship

 

1997 Bachelor of Science (B.S.) in Accounting, University of Florida