Oldershaw, Robert M.

Oldershaw, Robert M.




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Robert M. Oldershaw is a partner in the firm’s Miami office and is an accomplished trial lawyer who has tried more than 90 bench and jury trials in state and federal court. For more than 25 years, first in Illinois and for the past 20 years in Florida, he has also quickly disposed of claims against his clients through summary judgments and successfully handled hundreds of mediations. His knowledge, experience, and keen case and exposure evaluation abilities result in early resolution of claims, resulting in significant cost savings and limiting exposure for his clients.

Bob’s practice focuses on representing the world’s preeminent insurance companies, the hospitality and cruise line industries, and Florida cities and municipalities in personal injury and wrongful death defense; admiralty and maritime claims, including passenger, excursion and crew member claims; employment law including sex, age and race discrimination; municipal law, including civil rights violations under 42. U.S.C. §1983; and defense of premises liability and negligent security claims. He regularly drafts activity waivers and releases for businesses and recreational activity operators. On a daily basis, he counsels in-house counsel, corporate claims departments and insurance representatives regarding risk management, claims handling and routinely handles on site investigations and interviews. He has successfully handled arbitrations involving police, fire and general employee unions and was the Chief Litigation Counsel for the City of Hollywood, Florida from 2000 – 2009.

He is rated AV Preeminent™ by Martindale Hubbell®, the highest peer review rating possible, signifying that a large number of Bob’s peers rank him at the highest level of professional excellence for his legal knowledge, communication skills and ethical standards.


J.D., The John Marshall Law School
LL.M., Ocean & Coastal Law, University of Miami School of Law
B.A., Southern Illinois University


  • State:
    • Florida, 1996
    • Illinois
  • Federal:
    • United States District Court for the Southern, Northern and Middle Districts of Florida
    • United States Court of Appeals, 11th Circuit
    • U.S. Northern District Court of Illinois


Claims and Litigation Management Alliance (CLM)
National Association of Minority and Women Owned Law Firms (NAMWOLF)
The Dive Bar

Experience & Recognition

  • Recognition:
    • AV Preeminent™ by Martindale-Hubbell®, the highest peer review rating possible
  • Experience:
    • Success at trial of traumatic brain injury case where plaintiff claimed $3 Million in damages from a blow to her head and court awarded just over $9K.
    • Summary Judgment on claim of alleged over-service of alcohol to passenger who jumped overboard from cruise ship.
    • Summary Judgment for charter vessel on fall resulting in fractured ribs on sportfishing boat after plaintiff, an experienced fisherman, claimed the deck was too slippery from the mess created from the day’s fishing.
    •  Summary Judgment for cruise line in case involving fractured back from alleged dangerous condition.
    • Trial involving head-on collision between City employee and plaintiff where plaintiff’s demand in excess of $500,000.00. Jury found no permanent injury and awarded only $22,667.00 for medical and lost wages.
    • Federal jury trial where plaintiff, a female firefighter, alleged retaliatory discharge, discrimination for failure to provide gender separate bathrooms in firehouse, sexual harassment and disparate treatment. Plaintiff asked for statutory cap plus attorney’s fees and expenses and jury awarded $0.00 on claim of retaliatory discharge and discrimination.
    • Complete defense verdict in Federal jury trial where plaintiffs alleged they were falsely arrested, imprisoned, assaulted and battered by police officer.
    • Complete defense verdict in Federal jury trial where plaintiff alleged racial, national origin and age discrimination.
    • Won on appeal where plaintiff appealed granting of summary judgment in favor of City regarding lack of City’s duty to look for her after she was knocked off her bicycle by a hit and run driver on a street controlled by the FDOT. Summary Judgment affirmed.
    • Re-tried a false arrest and a statutory Notary Law violation against City of Hollywood and false Arrest against Officers. The trial in federal court was for damages only as the liability was affirmed on appeal, but the first jury awarded $750,000.00 and the Judge reduced to $450,000.00. The City felt items in the claim were duplicative and appealed. The 11th Circuit
      sent it back for re-trial on damages Hollywood. On re-trial, the plaintiff asked the jury to award $1,150,000.00 but the jury awarded Plaintiff $225,000.00.
    • $0.00 damage award in trial involving City’s Battalion chief involved in rear end collision.
    • Won multiple summary judgments on issues of open and obvious conditions after slip and falls on municipal property.
    • Over 60 subrogation bench trials involving motor vehicle accidents.