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Ashley W. Winsky

Partner
Paralegals
Erin Kirby804.956.2076
Lake Wiley804.956.2067
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Ashley Winsky is a partner at Gentry Locke’s Richmond office, specializing 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 Virginia 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), the Transportation Lawyers Association (TLA), the Transportation Defense Advocates Council (TDAC), and Immediate Past Chair of the Virginia Bar Association’s Transportation Section.  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).  She was selected as a “Rising Star” in Transportation by Legal 500.  For the past eleven 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)
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  • Years selected a "Virginia Rising Star" by peers
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  • Years noted by Chambers USA in Transportation
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  • Mountain resorts skied (and counting!)
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  • 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.

Education

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

Experience

  • First-chaired six-day federal trial involving allegations of negligence, punitive damages, and a request that the jury award $10 million, where plaintiff suffered an undisputed moderate traumatic brain injury and spinal fractures, and obtained a complete defense verdict for motor carrier and its driver
  • 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
  • In an admitted liability case, obtained jury verdict for tractor-trailer company within $5,000 of requested verdict
  • 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 and tanker companies and drivers involved in accidents
  • 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 of negligent hiring and retention claims for multiple motor carriers in various actions via motions to dismiss or summary judgment
  • 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 dismissal with prejudice of a wrongful death action for marine terminal on personal jurisdiction grounds
  • 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

Affiliations

  • Member, Trucking Defense Advocates Council (TDAC)
  • Member, Transportation Lawyers Association (TLA)
  • Member, American Trucking Association (ATA)
  • Immediate Past Chair of the Virginia Bar Association’s Transportation Section (2023)
  • Chair of the Virginia Bar Association’s Transportation Section (2022)
  • Vice Chair of the Virginia Bar Association’s Transportation Section (2020-2021)
  • 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 Kids Belong, Business Advisory Council Member

Speaking Engagements

  • Presenter, “Accident Reconstruction and the Impact of New and Improved Technology,” Transportation Lawyers Association Regional Seminar and Bootcamp, Chicago, IL, January 19, 2024.
  • Presenter, “Sit Down and Shut Up: The Art of Self-Awareness and Editing in Jury Trials,” Gentry Locke Seminar, Richmond, VA, October 12, 2023
  • Presenter, “Where Worlds Collide: Legal Issues at the Interstices Between Brokers and Motor Carriers,” Transportation Lawyers Association Annual Conference, San Diego, CA, April 29, 2023
  • Presenter, “You Start Walking My Way: Keys to a Successful Mediation,” Gentry Locke Seminar, Richmond, VA, September 28, 2022
  • 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

Awards

  • Influential Women of Law Award, Virginia Lawyer’s Weekly (2022)
  • 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, 2022), and for Personal Injury General: Defense (2021-2023)

Published Work

The results of client matters depend on a variety of factors unique to each matter. Past successes do not predict or guarantee future successes.
Ashley Winsky Fullbody Photo
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