Ashley Winsky is a partner at Gentry Locke’s Richmond office. She specializes in defending motor carriers against personal injury claims resulting from roadway accidents. She has over a decade of experience defending trucking companies in catastrophic injury, brain injury, spine injury, and wrongful death cases. Ashley responds to accident scenes throughout the Commonwealth and works with experts in the fields of human factors, biodynamics, and accident reconstruction. Her trucking clients range from small, family-owned operations to some of the nation’s largest truckload carriers.
Ashley also serves as lead counsel for an amusement park and water park, coordinating and defending all third-party injury claims. In addition, she assists a wide variety of businesses across the state in cases involving premises liability, breach of contract, defamation, intentional torts, and other business disputes. Confident and 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 is a member of American Trucking Association (ATA) and the Transportation Lawyers Association (TLA). She has been consistently recognized in the transportation arena by Chambers USA and was recently named an “Up and Coming” lawyer in Nationwide Transportation: Road (Carriage/ Logistics). In 2019, she was selected as a “Rising Star” in Transportation by Legal 500. For the past nine years, Ashley has been named a Super Lawyers “Rising Star” by her peers. She maintains an AV Preeminent peer rating with Martindale-Hubbell.
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.
- Virginia Polytechnic Institute and State University, B.A. summa cum laude
- 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 multiple defense verdicts at trial for tractor-trailer companies and drivers involved in automobile collisions
- 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 dismissal with prejudice of a negligence and assault and battery action, filed against a tractor-trailer company and its driver on a motion to dismiss
- Obtained favorable resolution for a tractor-trailer company whose driver was driving under the influence of alcohol and in possession of marijuana in a negligence action
- Obtained favorable resolution for a tractor-trailer company whose driver ran a red light in a personal injury action
- Obtained favorable resolution for a tank truck carrier involved in a multiple vehicle collision where a plaintiff rendering assistance suffered permanent injuries
- Obtained favorable resolution for a tank truck carrier in a chemical exposure case
- Obtained favorable resolution for a tractor-trailer company and its driver in collision involving a cyclist
- Obtained favorable resolution for a tractor-trailer company and its driver in a collision involving a pregnant motorist
- Obtained favorable resolution for fitness facility in action alleging wrongful death by drowning
- 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 dismissal with prejudice of a slip-and-fall action for a theme park
- Obtained dismissal with prejudice of an assault action for a theme park
- 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
- Virginia Bar Association, Transportation Law Section Council, Vice Chair (2020), Chair (2021)
- Virginia Kids Belong, Business Advisory Council Member
- Presenter, “The Thrill of Victory or Agony of Defeat, Which Will It Be?,” Transportation Lawyers Association Annual Conference, Olympic Valley, CA, June 24, 2021
- Presenter, “Transportation Update: Navigating the Insurance Market, Banking Environment, and Legal Landscape,” McGriff Webinar, Virtual, November 10, 2020
- Presenter, “Secrets to Conducting a Flawless Rapid Response,” Arkansas Trucking Seminar, Virtual, September 17, 2020
- Presenter, “Essentials of Trucking Accidents in Virginia,” Virginia Continuing Legal Education (VACLE), Virtual, August 13, 2020
- 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) (2019-2020); and an “Associate to Watch” in Transportation: Road (Carriage/Commercial) (2016-2018)
- Named to Super Lawyers “Virginia Rising Stars” for Civil Litigation (2013-2020) and General Defense (2021)
- Interview, “How Plaintiffs Use Commercial Vehicle Regulations to Turn Simple Negligence Into Driver Malpractice,” Corporate Counsel Business Journal, September 11, 2018.