Law Practice:

Chester focuses his practice on all areas of commercial, financial, and real estate litigation. He has experience representing commercial landlords in disputes against tenants, including forcible entry and detainer actions and breach of lease lawsuits. He has also litigated disputes concerning breach of non-compete, non-solicitation, or confidentiality agreements. Additionally, he counsels insurance companies on coverage matters. Before joining Cosgrave as an attorney, he was the summer law clerk in 2015.

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 is President of the Board of The Giving Tree NW, a local non-profit that provides resident services to affordable housing communities. He is also a member of the Multnomah Bar Association and the American Bar Association.


Outside of the office, Chester enjoys 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.


“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)