J. Richard Caskey

Top rated Estate & Trust Litigation attorney in Tampa, Florida

J. Richard Caskey, P.A.
J. Richard Caskey
J. Richard Caskey, P.A.

Practice Areas: Estate & Trust Litigation; view more

Licensed in Florida since: 2001

Education: University of Florida Levin College of Law

Selected to Super Lawyers: 2013 - 2024 Selected to Rising Stars: 2009 - 2012

J. Richard Caskey, P.A.

777 S. Harbour Island Blvd.
Suite 940
Tampa, FL 33602 Visit website

Details

J. Richard Caskey, a Tampa native, is the owner of his eponymous law firm based in Tampa, Florida. Renowned for his prowess in estate and trust litigation, fiduciary liability and probate law, he focuses his legal practice on guiding families and fiduciaries through the intricacies of estate, trust and guardianship administration. He also provides adept assistance across various administration facets while adeptly handling disputes through litigation, mediation and trial representation.

Earning his Juris Doctor with honors from the University of Florida Levin College of Law in 2001, Mr. Caskey received Book awards in mediation clinic, trial practice and income taxation. Prior to his law degree, he completed his Master of Business Administration degree with dual concentrations in finance and management, alongside a Bachelor of Science degree in accounting, both from the University of Florida in 2000 and 1997, respectively. It has been more than a decade since he founded J. Richard Caskey, P.A., to offer personalized attention to his clients. 

Admitted to The Florida Bar and all Florida state courts, Mr. Caskey holds esteemed recognitions, including being a Florida Supreme Court-certified circuit mediator, appellate mediator and a qualified court-appointed arbitrator. His distinction as a Fellow of The American College of Trust and Estate Counsel underscores his proficiency in this field.

Mr. Caskey has been repeatedly honored by Florida Trend magazine as a member of the Florida Legal Elite list and was acknowledged by The Best Lawyers in America for excellence in trusts and estates litigation. He was also the recipient of the James M. “Red” McEwen Memorial Award, acknowledging his exceptional service to the Hillsborough County Bar Association. In addition to engaging in several seminars and presentations, he has also been peer-review rated AV Preeminent* through Martindale-Hubbell and has received a perfect rating score of 10.0 on Avvo.

*AV®, AV Preeminent®, Martindale-Hubbell Distinguished and Martindale-Hubbell Notable are certification marks used under license in accordance with the Martindale-Hubbell certification procedures, standards and policies. Martindale-Hubbell® is the facilitator of a peer-review rating process. Ratings reflect the anonymous opinions of members of the bar and the judiciary. Martindale-Hubbell® Peer Review Ratings™ fall into two categories – legal ability and general ethical standards.

Practice areas

Estate & Trust Litigation

Focus areas

Will Contests

  • 100% Estate & Trust Litigation

First Admitted: 2001, Florida

Professional Webpage: http://www.caskeylaw.com/about-us/

Scholarly Lectures/Writings:
  • Florida Guardianship Practice, Chapter 6, “Use of Joint Assets” (The Florida Bar 7th ed. 2011; 8th ed. 2014; 9th ed. 2016; 10th ed. 2018)
  • Law School Symposium, Phi Alpha Delta, Keynote Speaker, Gainesville, FL 1999; 2000; 2001; 2002
  • Law Student Forum, The Florida Bar Real Property, Probate & Trust Law Section, Panel Member, Gulfport, FL 2004, Panel Member, Gainesville, FL 2002 
  • “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
  • “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
  • “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 
  • “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
  • “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
  • “Conflicts of Interests in Estate and Trust Matters”, St. Petersburg Bar Association; Continuing Legal Education, Featured Speaker, St. Petersburg FL, November 20, 2008
  • “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
  • “The Least Restrictive Alternative”, The Guardianship Team, Florida Legal Education Association (FLEA); Continuing Legal Education, Tampa, FL February 20-21, 2009
  • “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
  • “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
  • “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
  • “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
  • “Alleging Undue Influence”, Sarasota Bar Association; Continuing Legal Education, Featured Speaker, Sarasota, FL, January 26, 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
  • “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
  • “Rules of Judicial Administration Update”, Plant City Bar Association; Continuing Legal Education, Featured Speaker, Plant City, FL, April 8, 2011
  • “Nuts and Bolts of Probate, Trust, and Guardianship Practice”, 15th Annual Bench/Bar Conference, Hillsborough County Bar Association, Speaker, Tampa, FL, November 17, 2011
  • “Probate Law 2012”, The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education, Program Chair, Ft. Lauderdale, FL, March 22, 2012
  • “Adversary Proceedings in Probate”, The Florida Bar Elder Law Section, Probate Committee, Featured Speaker, May 8, 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
  • “Professional Practice and Conflicts in Estate Planning”, Venice Estate Planning Council, Featured Speaker, Venice, FL, May 14, 2012
  • “Marital Agreements: Inheritance and Other Rights of a Surviving Spouse”, Collaborative Divorce Institute of Tampa Bay, Featured Speaker, Tampa, FL, June 13, 2012
  • “Homestead Law Update”, Hillsborough County Bar Association Real Property, Probate & Trust Law Section, Featured Speaker, Tampa, FL, November 8, 2012
  • “Will Contests and Probate Litigation”, Stetson University College of Law, Guest Lecturer, Gulfport, FL, March 5, 2013
  • “Avoiding Litigation in Probate”, Hillsborough County Bar Association Real Property, Probate & Trust Law Section, Featured Speaker, Tampa, FL, November 14, 2013
  • “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
  • “Undue Influence?  Prove it!”, The Probate Team, Florida Legal Education Association (FLEA); Continuing Legal Education, Orlando, FL October 10-11, 2014
  • “Probate – A View from the Bench”, 18th Annual Bench/Bar Conference, Hillsborough County Bar Association, Moderator, Tampa, FL, October 30, 2014
  • “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
  • “Expansion of Standing to Protect Assets of the Elderly”, Hillsborough County F.A.S.T. Task Force, Featured Speaker, Tampa, FL, May 6, 2015
  • “Avoiding Litigation in Probate”, Suncoast Estate Planning Council, Featured Speaker, St. Petersburg, FL, December 3, 2015
  • “Guardianship and Probate Mediation”, 2015 UnProgram, Academy of Florida Elder Law Attorneys; Continuing Legal Education, Facilitator, Orlando, FL, December 5, 2015
  • “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
  • “Current Issues for Elder Exploitation”, Hillsborough County Bar Association Elder Law Section; Continuing Legal Education, Featured Speaker, Tampa, FL, April 8, 2016
  • “Elder Exploitation Issues for the Fiduciary”, St. Petersburg Bar Association; Continuing Legal Education, Featured Speaker, St. Petersburg FL, April 12, 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
  • “Probate Rules Update”, Hillsborough County Bar Association Real Property, Probate & Trust Law Section, Featured Speaker, Tampa, FL, November 17, 2016
  • “Mediation Issues in Guardianship”, Hillsborough County Bar Association Elder Law Section; Continuing Legal Education, Featured Speaker, Tampa, FL, January 20, 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
  • “Probate Power Hour – New Cases and Statutes”, The Probate Team, Florida Legal Education Association (FLEA); Continuing Legal Education, Orlando, FL October 20-21, 2017
  • “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
  • “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
  • “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
  • “Case Law Update”, Probate Law 2018, The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education, Tampa, FL, November 2, 2018
  • “What Every Planning Professional Should Know about Undue Influence”, Gulf Coast Estate Planning Council, Featured Speaker Trinity, FL, January 15, 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
  • “Mediation in Trust and Estate Matters”, Hillsborough County Bar Association RPPTL Section; Continuing Legal Education, Featured Speaker, Tampa, FL, May 9, 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
  • “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
  • “Top 10 Issues in Estate and Trust Mediations”, St. Petersburg Bar Association; Continuing Legal Education, Featured Speaker, St. Petersburg FL, December 10, 2019
  • “Staying out of Trouble!”, Professional Fiduciary Council of Florida, Panel Member, St. Petersburg, Florida, February 6, 2020
  • “Virtual Mediation During the Pandemic”, The Florida Bar Real Property Probate and Trust Law Section, Webinar (rpptl.org) April 3, 2020
  • “Making the Most of Mediation in Estate Disputes”, Orange County Bar Association; Continuing Legal Education, Featured Speaker, Orlando, FL, May 11, 2020
  • “Estate Mediations in the Remote Era”, Dade County Bar Association, Probate and Guardianship Committee, Featured Speaker, Remote Presentation, October 13, 2020
  • “Best Practices for Remote Mediations”, Hillsborough County Bar Association RPPTL Section; Continuing Legal Education, Featured Speaker, Remote Presentation, January 14, 2021
  • “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
  • “2021 Trust and Estate Symposium”, The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education, Program Chair, Webcast, May 7, 2021
  • “Introduction to the Virtual Law Office”, RPPTL Convention CLE: The Virtual Law Office, The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education, Co-Speaker, Marco Island, Florida, June 4, 2021
  • “Adoption and Dilution of Trust Interests”, ACTEC Florida Fellows 2021 Meeting, The American College of Trust and Estate Counsel; Continuing Legal Education, Co-Speaker, Palm Beach, Florida, July 21, 2021
  • “Goodstein, Gordon, and Goldfish (actually ‘Trust Stuff’ but we couldn’t think of another ‘G’ word)”, 41st Annual Legislative and Case law Update, The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education, Co-Speaker, Palm Beach, Florida, July 23, 2021
  • “Limiting Trustee Liability upon Termination, Resignation, Removal and Discharge”, 39th Annual Attorney/Trust Officer Liaison Conference, The Florida Bar Real Property, Probate & Trust Law Section; Continuing Legal Education, Co-Speaker, Palm Beach, Florida, August 20, 2021
  • “Reformation of an Unambiguous Trust Instrument”, HCBA Lawyer magazine, September 2005
  • “Equitable Adoption: Setting Things Right”, HCBA Lawyer magazine, November 2005
  • “Homestead and Amendment 10: Don’t Let the ‘Cap’ Out of the Bag”, HCBA Lawyer magazine, April 2006
  • “Changes in the Law Regarding Revocable Trusts”, HCBA Lawyer magazine, October 2006
  • “Looking for the Laughing Heir: Potential Expansion of Intestate Succession Laws”, The Florida Bar RPPTL ActionLine magazine, Summer 2007
  • “In Search of the Laughing Heir”, HCBA Lawyer magazine, June 2007
  • “Second District Court of Appeal Upholds Constitutionality of Elective Share”, The Florida Bar RPPTL ActionLine magazine, Spring 2008
  • “Protecting the Homestead; Protecting the Public: Waiver of homestead exemption from forced sale is unenforceable.”, HCBA Lawyer magazine, May 2008
  • “Homestead and Pay-on-Death Accounts: Two Completely Unrelated Cases of Interest” The Florida Bar RPPTL ActionLine magazine, Spring 2009
  • “Alleging Undue Influence:  Maybe You Don’t Have to Be So Presumptuous” The Florida Bar RPPTL ActionLine magazine, Spring 2010
Honors/Awards:
  • 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.
  • Rated AV Preeminent, Martindale-Hubbell.
  • Awarded the James M. “Red” McEwen Memorial Award for outstanding service to the Hillsborough County Bar Association.
  • Repeatedly selected by The Best Lawyers in America in the area of trusts and estates litigation.
  • Repeatedly selected by Florida Trend magazine as a member of the “Florida Legal Elite” list
Special Licenses/Certifications:
  • Florida Supreme Court Certified Circuit Mediator
  • Florida Supreme Court Certified Appellate Mediator
Bar/Professional Activity:
  • Florida Bar
  • Hillsborough County Bar Association (HCBA), Real Property, Probate & Trust Law Section (Chair 2005-07)  
  • Hillsborough County Bar Association (HCBA), HCBA Leadership Institute (Executive Committee 2008-09)
  • The Florida Bar, Rules of Judicial Administration Committee, Liaison to Probate Rules Committee (2011 – 2015)
  • The Florida Bar, Rules of Judicial Administration Committee, Liaison Sub-Committee, Vice-Chair (2012 – 2015)
  • The Florida Bar, Probate Rules Committee (2009 – 2015), Liaison to RPPTL Probate Law and Procedure Committee (2009 – 2011)
  • The Florida Bar, Probate Rules Committee (2009 – 2015), Vice-Chair (2011 – 2012; 2013 – 2015)
  • The Florida Bar, Liaison to Probate Rules Committee
  • The Florida Bar, Code and Rules of Evidence Committee (2018-present)
  • The Florida Bar Real Property, Probate & Trust Law (RPPTL) Section, ActionLine magazine (past Editor-in-Chief) (Substantive legal publication for the RPPTL
  • The Florida Bar Real Property, Probate & Trust Law (RPPTL) Section, Executive Council (2007 – Present)
  • The Florida Bar Real Property, Probate & Trust Law (RPPTL) Section, Probate Law and Procedure Committee (Member 2005 – Present)
  • Fellow of the American College of Trust and Estate Counsel (ACTEC)
  • Florida Qualified Court Appointed Arbitrator
  • United States District Court, Middle District of Florida
  • Past Editor-in-Chief, RPPTL ActionLine magazine - a substantive legal publication with quarterly circulation of approximately 10,000
  • Past Chairman, Hillsborough County Bar Association, Real Property, Probate & Trust Law Section
  • The Florida Bar Real Property, Probate & Trust Law (RPPTL) Section, Probate and Trust Litigation Committee (Chair 2018 – present; Vice Chair 2011 – 18)
  • Chair, Probate and Trust Litigation Committee, The Florida Bar RPPTL Section
Educational Background:
  • University of Florida, M.B.A. in Finance and Management, Poe Ethics Fellowship, 2000
  • University of Florida, B.S. in Accounting, 1997

Office location for J. Richard Caskey

777 S. Harbour Island Blvd.
Suite 940
Tampa, FL 33602

Phone: 813-608-0464

Selections

12 Years Super Lawyers
4 Years Rising Stars
  • Super Lawyers: 2013 - 2024
  • Rising Stars: 2009 - 2012

Top Lists

Top 50: Tampa Bay Super Lawyers: 2020 - 2021, 2024 Top 100: Florida Super Lawyers: 2020

Certificates and credentials

Additional sources of information about J. Richard Caskey

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