Tommy
D. Roebig

Training and Trial Certification

Roebig was born and raised in Jacksonville. He earned his undergraduate degree at Florida State University and his Juris Doctor in 1986 from Stetson University College of Law, where he was a Dana Scholar and a member of the National Moot Court Team. After graduation, he joined Wil Florin, who had founded the Clearwater firm the previous year — a partnership that has now lasted four decades.

Roebig holds three board certifications: Civil Trial Law certification from The Florida Bar and the National Board of Trial Advocacy, followed by national certification in Civil Pretrial Practice Advocacy. The credentials place his preparation of civil cases within both the pretrial and courtroom phases of board-certified practice. Each requires verified experience, peer and judicial review, and examination of a distinct discipline.

Civil litigation is often decided through investigation, expert development, depositions, motion practice, and the narrowing of what remains genuinely in dispute. Roebig’s public verdicts rest on that pretrial record.

He lectures at Stetson on negligence and wrongful-death damages, has served as an adjunct professor of civil law at St. Petersburg College, and speaks on trial tactics for the Florida Justice Association. In 2007, the Stetson Lawyers Alumni Association honored Roebig and Florin with its Paul May Meritorious Service Award, and in October 2019 Roebig was inducted into the Stetson University College of Law Hall of Fame — the eighty-ninth inductee in the school’s then-119-year history. The Florin|Roebig Courtroom at Stetson, funded and built by the firm in 1993 and later renovated, is used by Stetson trial teams and Florida’s Second District Court of Appeal. Those teaching and courtroom commitments connect his trial practice to recurring instruction in witness preparation, damages proof, negligence doctrine, and appellate presentation.

The Day-Spa Assault Cases

In 2014, Roebig and Wil Florin represented a woman identified at trial as Jane Doe who had been sexually assaulted during a treatment at Essentials Massage and Facial of New Tampa in Wesley Chapel. The therapist, Raul Delarosa, pleaded guilty to criminal charges and became a registered sex offender.

The civil case also concerned the business that supplied the room, the schedule, the materials, and the protocols. Essentials Massage argued that Delarosa was an independent contractor. Roebig presented evidence concerning control of the schedule, work setting, supplies, operating procedures, supervision, and retention. The jury found that Delarosa was the company’s employee under the working arrangement proved at trial.

The evidence also addressed notice. Approximately ninety days before the assault, the business knew or should have known that Delarosa had wrongfully touched another female patron at the same location and nevertheless kept him on the schedule.

The Pasco County jury returned a $47.4 million verdict: $420,000 for medical expenses, $12 million in compensatory damages for pain and suffering against the business and therapist, and $35 million in punitive damages against Delarosa for intentional conduct.

The allocation separated reimbursement for medical expense, compensation for personal injury, and punishment for intentional conduct. It identified which defendants were answerable for each component and connected the judgment to the evidence, instructions, and liability findings in that action — a verdict form that let jurors say precisely what they had decided and why.

In 2024, Roebig tried another Pasco County action against a day-spa corporation arising from an assault by a retained massage therapist. That action required its own hiring records, supervision proof, premises-control evidence, notice record, survivor testimony, and proof of the relationship between the business and the individual actor. The jury returned an $8 million verdict. The two actions involved different businesses, therapists, evidence, damages records, and jury findings, requiring each client’s proof to stand on its own.

Alcohol Service and Lifetime Care

In 2016, Roebig represented Patrick Osmond after a vehicle collision left him with an incomplete quadriplegic injury. The night began at a Brooksville Applebee’s, where a bartender served beer to a group that included minors before the driver struck a palm tree less than a mile from the restaurant.

Roebig presented the licensed seller’s age-verification process, corporate training, service practices, the chronology of consumption, collision evidence, and the medical and economic cost of permanent paralysis — the full arc from the first drink served to the last dollar of lifetime care.

After a two-week Hernando County trial, the jury assessed $41,956,474 in total damages, the largest contested jury verdict in Hernando County history. The verdict imposed more than $8.3 million in direct liability on the licensed seller and rested on the evidence concerning lifetime medical care, lost earning capacity, and noneconomic loss.

The Schwartz Wrongful-Death Trial

Dr. Steven Schwartz was a seventy-four-year-old kidney specialist in Tarpon Springs whose medical practice and rental properties had produced an estate estimated at twenty to thirty million dollars. In May 2014, he was found in the garage of his waterfront home, strangled, shot, and stabbed.

His second wife, Rebecca Schwartz, reported a burglary. Investigators found the DNA of handyman Anton Leo Stragaj on the doctor’s clothing. Stragaj said he had discovered the body and pointed to Rebecca. The killing drew national attention, including a 48 Hours episode and, after trial, a Dateline feature.

Steven Schwartz’s children filed a wrongful-death action against Rebecca Schwartz and Stragaj on May 25, 2016. The case proceeded for nearly nine years before trial in 2025. Rebecca had not been criminally charged by the time of trial. Roebig and Florin used civil discovery to develop a complex record involving family finances, estate planning, digital surveillance, forensic evidence, and competing accounts of what occurred inside the home.

The plaintiffs presented evidence concerning alleged embezzlement benefiting children from a prior marriage, funds directed to a marijuana grow house, a Verizon Wireless store purchased for a son, a revised will, and Dr. Schwartz’s intent to seek a divorce. They also alleged that Stragaj was sent to remove evidence, including the home-surveillance hard drive, and tried to recover the bullets.

In August 2021, Stragaj pleaded guilty to accessory after the fact, received an eight-year sentence with credit for time served, and was deported to Albania after his 2022 release.

A 2016 deposition in which Rebecca Schwartz repeatedly invoked the privilege against self-incrimination was shown during the civil trial. The jury could draw an adverse inference, but the inference did not substitute for proof: the plaintiffs still carried the burden of proving their wrongful-death case by a preponderance of the evidence. The trial team — Roebig, Florin, Shaun Cummings, and John Hart — connected the financial motive, the threatened divorce, the revised estate plan, the timing, the missing surveillance drive, and Stragaj’s conduct into an evidentiary account the jury could test.

On March 4, 2025, a Pinellas County jury found that Rebecca Schwartz had unlawfully and intentionally killed, or participated in procuring the death of, her husband. It awarded his children nearly $200 million — one of the largest contested wrongful-death verdicts ever returned in the nation, and an answer, delivered under the rules of evidence, to a question that had gone unresolved for more than a decade.

Other Florida Trial Work

Roebig has also tried commercial trucking-negligence and motorcycle-injury actions. The trucking matter required motor-carrier rules, carrier and driver records, vehicle and scene evidence, and accident reconstruction to be joined into a coherent liability account. The motorcycle matter required medical causation, future-loss evidence, witness preparation, and a jury’s allocation of responsibility. Each action called for its own experts, exhibits, witness sequence, jury instructions, and damages presentation.

His trial practice also includes negligent-security, product, medical-negligence, and other catastrophic-injury and wrongful-death claims.

Florin|Roebig

Roebig practices with Florin|Roebig in Palm Harbor, the firm he has helped lead since joining it in its second year. He has tried cases in Pasco, Hernando, Sumter, Pinellas, and other Florida venues, adapting to each court’s procedures, jury pool, witnesses, and physical evidence. His work runs from factual investigation, scene preservation, and governing records through expert selection and preparation, depositions, motion practice, jury presentation, verdict forms, and post-trial proceedings.

Across premises, liquor-liability, trucking, product, catastrophic-injury, and wrongful-death matters, his teams connect physical evidence to governing duties, prepare treating and fact witnesses, and translate the medical and economic proof for the particular injury. They build verdict forms that give jurors a clear path from breach to damages while adapting the record to the client, the defendant, and the governing law in each action.

Four Decades in Civil Trial Practice

Roebig’s teams build each record through investigation, expert work, depositions, and motion practice before presenting it to juries. His civil trial practice now spans four decades on behalf of injured people and families in Florida — a body of verdicts that has repeatedly reset what juries in the state’s most conservative venues will award when the proof supports it.