Robert Jameson focuses his practice on residential and commercial property insurance disputes, construction defect, and commercial litigation.

Prior to joining Woolsey Morcom, Robert practiced in the Jacksonville office of a well-known, national civil litigation firm. He successfully represented property insurance providers, Fortune 500 companies, and Florida businesses in state and federal court.

Robert began his legal career with the United States Navy where he was commissioned as a Judge Advocate General. As a Navy prosecutor, he tried a broad range of criminal cases and obtained convictions in several felony jury trials. He was eventually promoted to General Counsel for Naval Station Mayport in Jacksonville, Florida and was the Staff Judge Advocate to the Commanding Officer.

Prior to attending law school, Robert was appointed by President George W. Bush as a Special Assistant at the Department of Homeland Security. After leaving the Bush Administration, he spent six years working at the United States House of Representatives on government oversight and investigations. He was part of several high-profile congressional investigations including the attack on the United States Embassy in Benghazi. His private sector experience includes working as a Senior Associate at FTI Consulting, one of the largest financial consulting firms in the world, providing public affairs and government relations support.

Robert attended American University Washington College of Law and was a Note and Comment Editor on the Journal of Gender Social Policy and the Law

He enjoys spending time with his wife and two daughters. His hobbies include surfing, playing golf, and fishing. Robert continues to serve as a Lieutenant Commander in the Navy Reserve.

Josh Woolsey was a former Florida Prosecutor who has worked for Florida ’s Governor in Tallahassee and the United States Congress in Washington, D.C. Josh has successfully handled thousands of civil matters, resulting in the recovery of millions of dollars for his clients. He has successfully tried over 100 trials, with a success rate of over 95%, including trial success in numerous eight figure claims

Over the last few years alone, Josh has received in excess of $50 million in verdicts and judgments for his clients. He has obtained several million-dollar trial verdicts, as well as multiple million-dollar settlements for his clients. He has successfully litigated several high-profile cases and has represented celebrities, professional athletes, and large business executives. He prefers to represent hard-working individuals in need of aggressive legal representation.

Josh was named to the Business Journal’s top 40 under 40, Super Lawyers Magazine ’s top lawyers and Florida Trend’s Florida Legal Elite. He serves on the Board of Communities in Schools, is involved with numerous local charities and was a long-time big brother with Big Brothers Big Sisters. Josh has four sons with his wife Casey Woolsey and they live in Ponte Vedra, Florida.

Jonathan (“Jon”) O’Neil, a native Floridian from the Panhandle, is an experienced trial and appellate attorney in Florida insurance law. He handles complex disputes involving residential and commercial properties, with claims ranging from water intrusion, pipe leaks, windstorm, hurricane, tornado, business interruption, hail, fire and smoke, lightning, sinkhole and bad faith. Jon is also experienced in liability litigation including construction defect, personal injury, bodily injury, premises liability and professional malpractice. Since joining Pillar Property Law, he has focused on representing property owners and injured parties against insurance companies, corporations and reckless individuals.

Before joining Pillar, Jon worked for respected Tampa Bay law firms representing property owners statewide. His work spanned commercial and residential insurance disputes and gave him insight into how the insurance industry operates and adjusts claims, an advantage he uses to benefit clients.

Jon graduated with honors in the top 6% of his class from Stetson University College of Law, where he was an editor for the Stetson Journal of Advocacy and the Law and clerked for a Tampa Bay firm handling property insurance claims. He earned his BA in Political Science from the University of West Florida, graduating near the top of his class while running a small business full-time.

Jon and his wife Christine have two children, Everett and Lorelei. In his spare time, he enjoys fishing, gardening, travel, baseball and family adventures.

Molly Sapp is a native of St. Augustine, Florida. She is licensed in Florida, Texas and Colorado and focuses on residential and commercial property insurance litigation and personal injury. Molly graduated from Stetson University College of Law where she received the William F. Blews Pro Bono Award for her outstanding work in the community.

After graduation Molly began her career at a well-respected law firm in the Dallas area, defending one of the nation’s largest insurance carriers in personal injury lawsuits. After moving back to her home state, Molly decided to focus on people over insurance company profit. She thoroughly examines and addresses every aspect of her cases to ensure the best recovery for clients. Additionally, Molly is a registered patent attorney and has assisted clients across the nation with intellectual property registration and litigation.

Molly enjoys spending time at the beach with her husband and two sons

Paige Rhueby is an experienced trial lawyer dedicated to advocating for victims and the injured. Licensed in Alabama and Florida, she joined the firm after serving as an Assistant District Attorney in Jefferson County, Alabama, and as an Assistant State Attorney in Florida’s Fourth Judicial Circuit. She has tried hundreds of bench trials and dozens of jury trials, focusing on special victims, homicide and violent crime cases. Her experience sharpened her advocacy skills and fuels her commitment to achieving the best results for first-party property clients.

Born and raised in Knoxville, Tennessee, Paige developed a strong sense of community and volunteerism. She earned her undergraduate degree from the University of Tennessee, where she was recognized for volunteer service and leadership. She then attended Cumberland School of Law in Birmingham, Alabama, ranked among the top trial advocacy programs nationally. As a member of the National Trial Team, she gained courtroom experience while clerking for local District Attorney’s Offices and the U.S. Attorney’s Office for the Northern District of Alabama.

While in Alabama, Paige served as President of the Criminal Justice Section of the Birmingham Bar and Secretary of the Prescott House Child Advocacy Center Junior Board. She mentored law students and taught Human Trafficking laws to law enforcement and community groups. Now in Jacksonville, she is active in the Jacksonville Bar Association and continues mentoring law students.

Outside work, Paige enjoys time with her husband, two dogs, friends and family. Her hobbies include gardening, traveling, cheering on the Volunteers and attending concerts..

Erika Alba is licensed in both California and Florida and practices business law and commercial & residential property insurance dispute litigation. In her legal practice, Erika advises clients on matters including first property litigation, election law, and nonprofit governance and compliance. She has successfully represented clients before California and Florida state courts and agencies.

Prior to joining Woolsey, Erika practiced for over ten years in the Jacksonville office of an Am Law 100 law firm. Before entering private practice, Erika served as Senior Vice President to Fidelity National Financial, a Fortune 500 company, where she served as assistant general counsel managing regulatory and compliance matters.

Earlier in her career, Erika served as Assistant Chief Counsel for the California Department of Insurance, Office of the Insurance Commissioner. In this capacity, she was the bureau chief of the Insurer Compliance Bureau, a litigation unit representing the California Insurance Commissioner on insurer enforcement actions. As bureau chief, Erika personally litigated numerous unfair business and claims practices and managed the prosecution of all cases brought by her division. Erika began her legal career as a prosecutor for the Amador County District Attorney’s Office (California).

Erika also served as a volunteer Sacramento County Temporary Judge where, as a member of a panel of qualified attorneys, she presided as a trial judge in the Traffic and Small Claims divisions.

When not in the office, Erika can be found on a baseball field with her husband, watching their teenage son play highs school and travel baseball.

Recognition
Erika was named to The Business Journal’s 2012 Women of Influence list, an honor bestowed upon Jacksonville’s most influential women.

Education
Erika received her legal education from McGeorge School of Law, University of the Pacific, in California where she earned a Juris Doctor degree in 1993, and in 1998, a Masters of Law in Transnational Business Practice, As part of her LL.M. program, Erika worked in Sydney, Australia, as a visiting attorney for the corporate law and commercial litigation firm of Norton Smith & Co. Erika received a Bachelor of Arts in political science from California State University, Northridge.

Community Engagement
Active in the community, Erika is a past chair of the Associated Industries of Florida (AIF), one of the premiere business organizations in the state of Florida and served as the first female chair of AIF in its 101-year history. Erika is also a former chair of the Boys and Girls Club of Northeast Florida. She also served as a member of the board of trustees for Florida Tax Watch. She currently serves on the board of the St. Johns County Chamber of Commerce Foundation.

In 2006, Erika served on the Florida Governor’s transition team where she was assigned to the Citizens Review Group for the Office of Financial Regulation. In 2010, she served as Northeast Florida finance chair for Attorney General Pam Bondi.

Publications
Co-author, “Issues to Watch in Fla.’s Telehealth Genetic Counseling Bills,” Law360, February 3, 2023
Co-author, “Private Equity Portfolio Company Political Activity,” The Journal of Private Equity,
Summer 2016

Admissions
California
Florida

Jacob G. Sapp is a native Virginian who was raised in the Sunshine State. He is licensed to practice law in Florida, Texas, Kentucky and the U.S. District Court for the Middle District of Florida. Throughout those jurisdictions, Jacob focuses on representing clients in commercial and residential property insurance litigation. Jacob graduated from Stetson University College of Law where he competed on the nation’s top-ranked trial advocacy team, interned for Judges and worked as a research assistant in the Center for Excellence in Higher Education Law & Policy.

After graduation, Jacob began his career working in Texas as a Compliance Officer in Higher Education, and then as outside General Counsel to Colleges and Universities.

Previously, Jacob worked as an assistant state attorney in Florida’s Fourth Judicial Circuit where he efficiently and tenaciously prosecuted cases on behalf of the citizens of Florida. At Pillar Property Law, Jacob brings that same zealous advocacy to clients, no matter the size of the case or the challenge.

Outside of the office, Jacob prioritizes his family, raising his two sons with his wife, fellow Pillar Property Law Attorney, Molly Sapp.

Maria C. F. Cruz is an associate attorney in the litigation department, focusing on construction, real estate, condominium, business and complex commercial litigation. She is dedicated to achieving favorable outcomes for her clients through strong advocacy and legal expertise.

Maria earned her Juris Doctor from Ave Maria School of Law in 2022, receiving the CALI Excellence for the Future Award in Business Planning and Copyright Law and the Cardinal Newman Scholarship. She served as Treasurer and later President of the Federalist Society, building her leadership and advocacy skills.

Her legal experience includes interning with the Honorable Rima Ghandour in private practice and the Law Office of Matthew P. Flores in Southwest Florida. Before joining the firm, she worked at a respected civil litigation firm representing developers, contractors, business owners and homeowners associations.

Maria is admitted to practice in Hawai‘i and the United States District Court for the District of Hawai‘i, both since 2022, and is an active member of the Hawaii State Bar Association, the Federalist Society and the National Association of Asian American Professionals. She is also admitted to the Florida Bar.

Currently, Maria is pursuing an LL.M. in Risk Management and Compliance from Texas A&M University College of Law, expected in 2025.

Outside of work, she enjoys time with family, especially her nieces and her two dogs, Quipuha (Bullmastiff) and Chebot (English Bulldog). Her hobbies include graphic design, cooking and baking, weight training, surfing and hiking.

David C. Gilbert is a native to New Hampshire but has called several states throughout the East Coast home. He is licensed to practice law in Florida and focuses on representing clients in commercial and residential property insurance litigation. David graduated from the University of Florida Levin College of Law, where he competed on the alternative dispute resolution team and interned with Catholic Legal Services, the Department of Children and Families, and the State Attorney’s Office for Florida’s Eighth Judicial Circuit.

After graduation, and prior to joining Woolsey Morcom, David served three years working as an assistant state attorney in Florida’s Fourth Judicial Circuit, where he effectively prosecuted cases ranging from misdemeanors to first-degree felonies. In this challenging and demanding role, David placed the care of victims and the pursuit of justice as his priority in each case. At Woolsey Morcom, David brings that same care and unwavering dedication to our clients, with the determination to meet every challenge head on.

Outside of the office, David prioritizes his family, relationships, and educational growth.

Thomas focuses his practice on commercial and residential property insurance disputes, but has experience in everything from construction defect litigation to corporate governance advisement. Thomas maintains a strong interest in various legal disciplines and is passionate about protecting his clients from corporate bad actors and negligent tortfeasors.

Thomas completed both his undergraduate degree and postgraduate education at the University of Georgia. While attending the University of Georgia School of Law, he completed a dual degree program, earning his Master’s in Business Administration from the University of Georgia’s Terry College of Business simultaneously with his J.D. His Masters in Business Administration has been an extremely helpful tool in understanding and evaluating the economics of litigation and insurance disputes.

Thomas is licensed to practice law in both South Carolina and Georgia. He is also an experienced mediator in the state of Georgia which has instilled a great understanding and appreciation of the advantages of alternative dispute resolution strategies.

Prior to joining Woolsey Morcom, Thomas developed his extensive litigation experience at a nationwide insurance defense firm with an office in Charleston. This experience provided Thomas with invaluable insight into how insurance companies value and defend their claims.

As a native of Savannah, Georgia, Thomas has spent his entire life on the coast. When he’s not working, he’s likely fishing, hunting, or enjoying the outdoors with his wife and son. Both his upbringing and education have instilled a deep love for the Georgia Bulldogs, and he can often be found watching a game in Athens during the fall.

Trevis R. Loree is a native of San Antonio, Texas, and is licensed to practice law in the state of Texas. Trevis focuses on representing clients in residential and commercial property insurance litigation, as well as construction disputes. Trevis earned his law degree from the UNT Dallas College of Law, where he discovered his passion for civil litigation.

Following law school, Trevis began working alongside his father, Robert W. Loree, a seasoned attorney with over 40 years of experience representing policyholders against insurance companies that underpaid or denied valid storm damage claims. Trevis credits his father with teaching him everything he knows about standing up for policyholders. After Robert’s passing in June 2024, Trevis made it his mission to carry on his father’s legacy and continue zealously advocating for clients against insurance companies.

Outside the courtroom, Trevis enjoys spending time with his family, his dog Sammy and his cat Guppy. His hobbies include golfing, working out and attending live music events.

Wesley Barr is an accomplished litigation attorney with more than 15 years of experience in property insurance disputes, securities litigation, product liability and personal injury matters. Mr. Barr works out of the firm’s Honolulu, Hawai’i office and focuses his practice on representing individuals, businesses and nonprofits in first party property disputes with their insurers.

Prior to joining the firm, Mr. Barr served as a regulatory enforcement attorney for the State of Hawai’i where he worked to protect consumers from unfair and deceptive business practices. Wes was also previously in private practice based in New Orleans, Louisiana specializing in securities litigation, personal injury, and insurance bad faith claims. Mr. Barr has successfully litigated jury trials, AAA and FINRA arbitrations, and administrative hearings across several states.

Mr. Barr graduated from University of Florida, Levin College of Law and received a Master’s degree from Tulane University. He has been nominated by his peers as a Super Lawyer in personal injury, bad faith insurance and business litigation for several years. He previously served on the Louisiana Attorney Disciplinary Board and serves as a court appointed Guardian Ad Litem in Hawai’i.

Wes lives in Honolulu, Hawaii with his wife and newborn daughter. He enjoys surfing, playing golf, hiking and beach days with his family. He is active in his local church and serves as an officer of the Hawaii Christian Legal Society. Outside of his legal practice, Wes enjoys giving back to the community through legal aid services, homeless outreach and court appointed guardianships.

Lorenzo N. Lima is a Hawaiʻi-licensed attorney with litigation experience and a professional background spanning courtroom advocacy and the insurance industry. His practice focuses on representing property owners in first-party insurance claims, with an emphasis on clear strategy, thorough preparation, and effective advocacy.

Mr. Lima previously served as a Felony Deputy Prosecuting Attorney with the Honolulu Prosecutor’s Office, where he appeared regularly in Circuit and District Courts and tried numerous cases to verdict. Through this work, he developed strong trial skills in motion practice, witness preparation, evidentiary hearings, and courtroom presentation—experience that informs his approach to complex, fact-driven insurance disputes.

In addition to his litigation background, Mr. Lima has direct experience working within the insurance industry, where he evaluated and investigated property and casualty claims, analyzed coverage and exposure, and participated in mediations and formal hearings. This experience gives him valuable insight into how insurers review, value, and defend claims, allowing him to advocate effectively for policyholders when coverage is delayed, undervalued, or wrongfully denied.

Mr. Lima is deeply committed to serving the local community in Hawai’i. He earned his Juris Doctor from the William S. Richardson School of Law at the University of Hawaiʻi at Mānoa and is admitted to practice in the State of Hawaiʻi and the U.S. District Court for the District of Hawaiʻi. He is fluent in Portuguese and Spanish.

Mr. Lima is committed to standing up for Hawaiʻi property owners and ensuring they receive the full benefits and fair treatment promised under their insurance policies.

Dennis D. Green, Jr. focuses his practice on residential and commercial property insurance disputes, construction-related claims, and complex coverage litigation. He represents policyholders and property owners in matters involving denied, delayed, and underpaid insurance claims, as well as related contractual and statutory disputes.

Prior to joining Pillar Property Law as Of Counsel, Dennis operated his own practice handling property insurance litigation and civil disputes throughout Florida, Texas, and Alabama. He has substantial experience litigating first-party property insurance claims from pre-suit through trial, including matters involving coverage interpretation, valuation disputes, and insurer compliance with applicable insurance statutes.

Dennis previously served as an Assistant District Attorney in Harris County, Texas, where he gained extensive courtroom and trial experience prosecuting criminal cases. He also served as a Deputy Sheriff, providing him with a practical, enforcement-based understanding of investigations, evidence, and litigation strategy.

In addition to his legal background, Dennis is a Florida Certified Building Contractor, bringing valuable technical insight to construction and property damage disputes. He is licensed to practice law in Florida, Alabama, and Texas, and has appeared in state and federal courts across multiple jurisdictions. His practice is informed by a practical, results-driven approach, with an emphasis on early case assessment, strategic positioning, and efficient resolution.

Before entering the legal profession, Dennis developed a disciplined, team-oriented mindset through competitive athletics, including playing collegiate football at Florida State University. Outside of his practice, he enjoys sports, fishing, and hunting, and values time spent coaching football, mentoring young professionals, and with his family.