Ashley W. Winsky


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  • George Mason University School of Law, JD, 2009
  • Virginia Polytechnic Institute and State University, BA, summa cum laude, 2006
  • Virginia
  • West Virginia
  • U.S. District Court for the Eastern District of Virginia
  • U.S. District Court for the Western District of Virginia
  • U.S. District Court for the Southern District of West Virginia

Member, Transportation Lawyers Association (“TLA”)

Member, American Trucking Associations (“ATA”)

Ashley is a trial lawyer whose practice focuses primarily on servicing clients in the transportation industry.  She defends motor carriers against personal injury claims arising out of roadway accidents. Ashley has defended trucking companies in catastrophic injury, brain injury, spine injury, and wrongful death cases. Ashley responds to accident scenes and works with experts in the fields of human factors, biodynamics, and accident reconstruction.

In addition, Ashley has defended railroads, automobile manufacturers, product manufacturers, bus companies, amusement parks, and business owners against a wide array of personal injury, premises liability, and product liability claims. 

A portion of Ashley’s practice is devoted to representing individuals in select personal injury and wrongful death cases.

Ashley has first-chaired over a dozen trials to defense verdicts in state and federal court, before both judge and jury.  She has successfully briefed and argued numerous dispositive motions to short-circuit protracted litigation.  Ashley has conducted hundreds of depositions and examinations for trial purposes.  She routinely evaluates medical records and prepares experts for depositions and trial testimony.

In addition to her trial experience, Ashley has extensive experience negotiating cases to settlement through mediation and without the aid of a neutral third party.

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Ashley Winsky
T: +1 804 775 1207F: +1 804 698 2207Gateway Plaza
800 East Canal Street
Richmond, VA 23219-3916

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.

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 settlement for plaintiff in a wrongful death case.

Obtained favorable resolution for tractor-trailer company 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.

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 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.

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. 

Defended employers in arbitration against claims of wrongful discharge and obtained denial of grievance rulings.

Named an "Associate to Watch" in America's Leading Lawyers for Business, Transportation: Road (Carriage/Commercial), Nationwide, Chambers USA, 2016-2018

Named to "Virginia Rising Stars," Civil Litigation: Defense, Super Lawyers, Thomson Reuters, 2013-2018

Interview, "How Plaintiffs Use Commercial Vehicle Regulations to Turn Simple Negligence Into Driver Malpractice," Corporate Counsel Business Journal, September 11, 2018
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
Presenter, "The Overlap Between the FMLA, ADA, and Workers' Compensation," Workers' Compensation Law and Practice Seminar, October 2012