Law Practice:

Chester is a trial lawyer who focuses his practice on all areas of commercial, financial, and real estate litigation. He often represents commercial landlords in disputes against tenants, including forcible entry and wrongful detainer actions and breach of lease lawsuits. He also represents professionals, including accountants and lawyers, in malpractice and related actions. He has also litigated corporate disputes concerning breach of non-compete, non-solicitation, and confidentiality agreements.  Additionally, he counsels insurance companies on coverage matters, and litigates those matters as well.

Representative Cases

In a bench trial, obtained judgment in favor of hotel owner in an action brought by adjoining property owner seeking express and implied easements burdening hotel’s property.

Obtained summary judgment, on grounds of ineffective service of process and statute of limitations, in residential tenant’s favor on claim brought by tenant’s former landlord (pro bono representation).

Successfully and favorably resolved, on the fourth day of jury trial, $20 million negligence, fraud, and breach of fiduciary duty claims brought against CPA by former clients.

Obtained summary judgment in insurer’s favor on claims brought by insured seeking benefits pursuant to insurance policy, and damages for insurer’s alleged wrongful failure to pay.

In a bench trial, obtained judgment in favor of commercial landlord in action brought by former tenant alleging breach of lease and racial discrimination.

Obtained judgments of restitution in favor of landlords in multiple forcible entry and wrongful detainer actions, including through trial.

Education & Bar Admissions:

Chester earned his undergraduate degree in economics, cum laude, from The George Washington University. Later, he graduated magna cum laude from Lewis & Clark Law School. At Lewis & Clark, he was named a member of the Cornelius Honor Society, a group of students selected by the law faculty for their scholarship, leadership, and contribution to the law school community. During law school, Chester worked as a law clerk for the Financial Fraud and Consumer Protection Section of the Oregon Department of Justice. He also served as Associate Editor of Environmental Law, the nation’s oldest law review dedicated solely to environmental issues.

Chester is admitted to the Oregon State Bar, and the United States District Court for the District of Oregon.


Chester served as President of the Board of The Giving Tree NW, a local non-profit that provided resident services to affordable housing communities in the Portland Metro area. He is also a member of the Multnomah Bar Association and the American Bar Association.


Outside of the office, Chester enjoys running, playing pick-up basketball, and playing the guitar (with all EQs at noon and just a little bit of reverb). In a past life, Chester wrote short fiction and essays. He hopes to publish some of his work one day.


“The Management Accountant’s Ethical Approach to Litigation: The Statement of Ethical Professional Practice and its Application to Litigation” – March 17th, 2021
Chester and Amber presented to IMA members on what plaintiffs, defendants, and expert witnesses can expect from a lawsuit, including what they wished their clients had known before they called with a problem.

“Additional Insured Issues in Washington and Oregon”
In November 2019, Chester spoke at The Seminar Group‘s Northwest Insurance Law Seminar. He spoke about issues related to additional insured endorsements, recent Oregon court decisions implicating the duty to defend, and the scope of “ongoing operations.” The presentation can be viewed here.


“Farmers, Ranch, and Agriculture”
Insurance Law Bar Book, Oregon State Bar, 2019


“Oregon Rising Star,” Super Lawyers magazine, Civil Litigation (2019, 2020, 2021)