Courtney L. Winston

Courtney L. Winston

Meet Courtney

Courtney Leigh Winston has a decade’s worth of trial experience. She has tried dozens of cases in general district and circuit courts and has represented clients in criminal and civil trials. Her wide breadth of legal knowledge allows Courtney to talk to her clients about all the implications of our justice system.

Courtney got her first taste of the courtroom while working at the Central Virginia Legal Aid Society, where she represented clients in unemployment and landlord-tenant disputes.  From there, she transitioned to criminal defense and worked alongside David P. Baugh. In her previous work as a criminal defense attorney and in her current work as a civil plaintiff’s attorney, Courtney dedicates her career to representing people when the odds are stacked against them. At Allen & Allen, she prides herself on giving a voice to the voiceless and is the fearless advocate that her clients need.

Clients describe Courtney as responsive, compassionate, and willing to go the extra mile. Her personal injury cases have reached six-figure settlements and verdicts. She makes it a point to be the most prepared person in the courtroom and enjoys “nerding out” about legal nuances. Courtney’s practice includes motor vehicle crashes, premises liability, wrongful death, dog bites, pedestrian, and sexual abuse cases. She is currently the Editor of the Allen & Allen blog.

Courtney enjoys practicing yoga and is a certified Bikram yoga instructor. In her spare time, she learns about new places and cultures through travel and food, and is particularly fond of the Caribbean. She is married to the restaurant industry (her husband owns a restaurant and brewery) and takes full advantage of the Richmond dining and arts scene.

Courtney speaks Spanish. She had a destination wedding in Mexico and travels back to Isla Mujures as often as she can.


  • Trial Attorney, Allen, Allen, Allen & Allen (2021-Present)
  • Trial Attorney, Christina Pendleton & Associates (2019-2021)
  • Trial Attorney, David P. Baugh, PLC | Courtney Leigh Winston, PLC (2013-2019)
  • Volunteer Attorney, Central Virginia Legal Aid Society (2012-2013)

Bar Admissions

  • Licensed to practice law in the Commonwealth of Virginia
  • United States Eastern District of Virginia


  • Juris Doctor, Howard University School of Law (2012)
  • Bachelor of Arts in Spanish and Foreign Affairs, University of Virginia – Dean’s List (2009)
  • University of Virginia in Valencia, Study Abroad

Professional Affiliations

  • Lewis F. Powell, Jr. American Inn of Court
  • Richmond Bar Association
  • Virginia Trial Lawyers Association (VTLA)
  • American Association for Justice (AAJ), Leadership Academy 10
  • National Trial Lawyers, Top 40 Under 40
  • Society of Women Trial Lawyers
  • Trial Guides Editorial Board

Speaking Engagements

  • “How to Handle Common Deposition Scenarios,” Richmond Bar Association (2023)
  • “Managing Client Expectations at the Initial Consultation,” American Association for Justice (AAJ) Annual Convention (2023)
  • “Overturning Rocks, Kissing Frogs, and Other Tools of Discovery,” Society of Women Trial Lawyer Annual Conference (2023)
  • “The Ethics of Crafting the Story,” North Dakota Association of Justice Annual Seminar (2023)
  • “Ethics of Storytelling,” Virginia Trial Lawyers Association (VTLA) Advocacy Seminar (2022)

Written Works

  • “Civil and Criminal Sexual Assault Liability in Virginia,” The Virginia Trial Lawyers Association The Journal, Vol. 29, No. 2 (2023)
  • “Set Client Expectations at Intake,” American Association for Justice Trial Magazine (October 2023)

Sexual assault: $425,000

The details of this settlement are confidential.

Shelley from Short Pump

My fiancé and I were hit by a speeding driver as we were exiting a parking lot. The impact turned our car around. The paramedics came and inspected me, and...

Rosa from Richmond

I was out driving when a car ran a red light, and it hit me so hard it knocked me to the other side of the street. My car was...

Can I sue for sexual assault?

  • February 1, 2024
  • Blog

I recently received a call from a woman who was sexually assaulted. She filed a police report, and her assailant is currently facing criminal charges. She contacted me because she...

The verdict is in! Allen & Allen attorneys rate legal shows and films

  • January 17, 2024
  • Blog

What is your favorite legal movie or TV show of all time? My favorite legal movie is The Verdict.  It is far more realistic than most and tells a gripping...

Sober Ride Home a success in 2023

  • January 5, 2024
  • News

New Year’s Eve was a little safer in Central Virginia, as Allen & Allen hosted the tenth year of their Sober Ride Home program! The firm partnered with multiple businesses throughout...