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Ashley Winsky, Gentry Locke partner in our Richmond, VA office

Ashley W. Winsky

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Jennifer White804.297.3706
Angela Foster804.297.3707
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Ashley Winsky, a partner and trial lawyer in the firm’s Richmond office, maintains a diverse litigation practice. Ashley listens to her clients and works tirelessly to advance their objectives. Comfortable in the courtroom, Ashley has tried cases before both judge and jury in state and federal court. She is equally effective in mediating disputes to save clients the expense and exposure that comes with protracted litigation.

Ashley’s clients have described her as “compassionate, empathetic, and tactful” and “energetic, dynamic, and very tenacious.”  Her peers have labeled her “a stand-up trial lawyer who is tenacious, ambitious, and hardworking” and “utterly devoted to the client’s cause, imminently capable, and always professional.”

Ashley has nearly a decade of experience defending motor carriers, railroads, amusement parks, bus companies, product manufacturers, and business owners against a wide array of personal injury claims. Ashley has also represented individuals in wrongful death and catastrophic injury claims. She has been consistently recognized in the transportation arena by Chambers USA, named a “Rising Star” in Transportation by Legal 500, and named a “Virginia Rising Star” by Super Lawyers.

  • Spots on my Dalmatian (approximately)
  • Years selected a "Virginia Rising Star" by peers
  • Years noted by Chambers USA in Transportation
  • Mountain resorts skied (and counting!)
  • People are surprised when they hear...

    That I represent tractor-trailer companies. I never imagined I would be a trucking lawyer, but I truly love the variety and complexity of these cases. Most jurors are not keen on sharing the highway with big rigs. They see intimidating 18-wheelers and not the dedicated, hardworking drivers on the job. I enjoy the challenges these cases present, and I have been fortunate to meet some really amazing people in the industry along the way.

  • You joined Gentry Locke in 2019, but you’ve used a Gentry Locke umbrella since 2007. Why?

    It’s a quality umbrella! In law school, I interviewed for a job with Gentry Locke on a rainy day, and the firm gave me an umbrella. It’s been my go-to umbrella ever since. Twelve years later I joined the firm, and now I get to give Gentry Locke umbrellas to my clients.


  • Antonin Scalia Law School – George Mason University, J.D. 2009
  • Virginia Polytechnic Institute and State University, B.A. summa cum laude, 2006


  • Second-chaired three-week federal trial involving allegations of fraud against a former executive of an aviation software company and a demand in excess of $20 million and obtained a favorable defense verdict while also securing a counterclaim verdict for the client
  • First-chaired jury trial to defense verdict for a waterpark in a premises liability action involving the operation of an amusement device and allegations of lifeguard negligence
  • Obtained 6.5 million dollar settlement for plaintiff in a premises liability case, which was reported in Virginia Lawyers Weekly as the second largest settlement in 2018
  • Obtained 1.9 million dollar settlement for plaintiff in a wrongful death case, which was believed to be a record-setting settlement in the rural county where the case was filed
  • Obtained dismissal with prejudice of a personal injury action, filed against a tractor-trailer company and its driver, arising out of a roadway accident in the months before trial was scheduled to commence
  • Obtained favorable resolution for tractor-trailer company and its driver in collision involving a cyclist
  • Obtained favorable resolution for fitness facility in action alleging wrongful death by drowning
  • Obtained defense verdicts at trial for tractor-trailer drivers involved in automobile collisions
  • Obtained defense verdict at trial for a theme park in a case involving allegations of assault and battery to a minor
  • Obtained defense verdict at trial for a theme park in a premises liability action involving an injury to a minor
  • Obtained favorable resolution in a defamation case
  • Successfully defended entertainment venue against copyright infringement claims
  • Successfully tried a breach of contract claim to bench verdict for a manufacturer of pool products
  • Served as local counsel for a component part manufacturer in a product liability action involving pourable gel fuel and obtained nonsuit
  • Defended railroad in an action alleging take-home asbestos exposure to an independent contractor’s family member and obtained nonsuit
  • Represented railroad in casualty, FRSA and FELA litigation
  • Represented software company in federal court litigation involving breach of contract, tortious interference, and conspiracy claims
  • Tried numerous personal injury cases to defense verdict at trial for public transit authority
  • Tried multiple workers’ compensation cases to defense verdict before the Virginia Workers’ Compensation Committee for public transit authority


  • Member, Transportation Lawyers Association (TLA)
  • Member, American Trucking Association (ATA)
  • Licensed in Virginia and West Virginia
  • Admitted to practice before the U.S. District Courts for the Eastern District of Virginia, Western District of Virginia, and Southern District of West Virginia

Speaking Engagements

  • Presenter, “Ethics for Motor Carrier In-house Counsel,” American Trucking Association’s Forum for Motor Carrier General Counsel, Santa Ana Pueblo, NM, July 15, 2018
  • Presenter, “I am not a Professional: Rejecting the Heightened Standard of Care for Truck Drivers,” Transportation Lawyers Association Annual Conference, Orlando, FL, May 3, 2018
  • Presenter, “Ethical Quandaries in Light of the Cloud, Social Media and Data Breaches,” American Trucking Association’s Forum for Motor Carrier General Counsel, Beaver Creek, CO, July 16, 2017


  • Named a “Rising Star” in the practice of Transportation: Rail and Road – Litigation by Legal 500 US (2019)
  • Named an “Up and Coming” attorney in Chambers USA America’s Leading Lawyers for Business, Transportation: Road (Carriage/Logistics) (2019); and an “Associate to Watch” in Transportation: Road (Carriage/Commercial) (2016-2018)
  • Named to Super Lawyers “Virginia Rising Stars” for Civil Litigation (2013-2019)
  • award

Published Work

Ashley Winsky, Gentry Locke attorney in Richmond, VA office