Jonathan (“Jon”) Hollan is a highly accomplished, Lexington-based trial lawyer. He has spent his career representing those in Kentucky and beyond who were injured by the wrongful acts of others. He has exclusively handled personal injury cases from the outset of his career, with a primary focus on cases involving semi-trucks, tractor-trailers, trucking companies, commercial vehicles, severe automobile crashes, brain injuries, and bad-faith insurance practices.
Jon is a passionate litigator with a proven record at trial. His Kentucky career has spanned from courtrooms in Pikeville to Paducah. He has tried numerous injury cases to verdicts statewide, quickly becoming one of the most prolific Plaintiff’s lawyers throughout the Commonwealth. In 2019, Jon made history as one of the youngest attorneys in Kentucky to secure a seven-figure jury verdict, a testament to his dedication and skill.
Notable Settlements & Verdicts
Insurance Bad Faith
$14,000,000
Wrongful Death
$12,000,000, $5,200,000
Truck & Commercial Vehicle
$6,250,000, $6,100,000, $6,000,000, $4,100,000, $4,000,000,
$4,000,000, $3,600,000, $2,400,000, $2,000,000, $1,800,000, $1,700,000,
$1,600,000, $1,500,000, $1,300,000, $1,000,000
Personal Injury
$2,000,000, $1,250,000, $1,000,000
Practice Style
Jon is a perpetual learner, constantly seeking to expand his knowledge and skills. He studies trials nationwide and is recognized within the NTL’s Top Ten Trucking Lawyers.
Each case presents a unique opportunity to Jon, as he embraces the challenge of complex cases and utilizes technology and creativity to present each client’s story in the manner that is required for full justice.
Within the last several years, Jon has established himself as one of the country’s top legal authorities on cases involving CSP and DSP models, such as Amazon delivery vehicle crashes and accidents involving FedEx Ground contractors. Lawyers throughout the country have sought Jon’s experience and guidance on all matters of trucking, ranging from crashes involving defective brake crashes to driver fitness issues to spoliation of evidence from data recording devices. His dedication to identifying the root causes of tractor-trailer accidents has resulted in some of the largest known pre-trial trucking settlements obtained in the area over the last several years.
Speaking Engagements & Professional Accomplishments
National Trial Lawyers
Big Truck & Auto Convention, 2024 – Panelist & Featured Speaker
Annual Trial Lawyers Convention, 2025 – Panelist & Featured Speaker
Kentucky Justice Association
Annual Seminar, 2022 to present – Presenter, 2022
Tennessee Trial Lawyers Association
Seminar, 2022 – Presenter
WKYT News
Truck Talk, 2024 to present – Featured Guest
Associations and Leadership
Kentucky Justice Association, Executive Committee
American Association for Justice
The Trucking Litigation Group
Academy of Truck Accident Attorneys
The National Trial Lawyers
Melvin M. Belli Society
Alumni Council, Brandeis School of Law
Personal
Outside the law, Jon enjoys reading, golfing, and traveling with his wife and their young son, with no destination dearer than his hometown mountains of eastern Kentucky.