Seth Craywood

Seth A. Caywood is an attorney with Holbrook Leavitt & Associates. Seth earned his undergraduate degree in music education from the University of Tulsa in Tulsa, Oklahoma, and was a high school band director prior to starting law school. He enrolled at the University of Tulsa College of Law, where he earned his J.D. in 2011 and passed the bar the same year.

Seth spent the first 14 years of practice defending insureds through their insurance carriers, working closely with his clients and their insurance adjusters to prepare matters for trial or resolution. In April of 2026 he joined Holbrook Leavitt and Associates as an experienced litigator and trial advocate bringing his experience and knowledge of the workings and thought processes of insurance companies to the firm.

Seth takes a pragmatic approach to litigation looking for the most efficient path to the most desirable outcome. He works diligently to educate clients about how the legal system operates to remove the cloak of mystery surrounding the courthouse and alleviate anxieties.

Known for his no non-sense attitude, Seth ensures that his clients are well informed and their cases are handled efficiently.

Originally from Wichita, Kansas, Seth’s family brought him back to the Broken Arrow in 1986 and he has been a member of the community ever since. He graduated from Broken Arrow High School where he met the woman who would eventually become his wife. Seth has 5 daughters and two grandchildren. He spends his free time coaching his youngest children in volleyball, working on his motorcycle, and doing projects for his wife.

Practice Areas

• Breach of Contract
• Breach of the Duty of Good Faith and Fair Dealing (Bad Faith)

Education

• University of Tulsa 2007
  • BA in Music Education
• The University of Tulsa College of Law 2011
  • J.D.

Bar Admissions

• Oklahoma 2016
• Northern Districts of Oklahoma
• Western Districts of Oklahoma
• Eastern Districts of Oklahoma
• 10 Cir. Court of Appeals
• Cherokee Nation Tribal Court

Professional Memberships

• Oklahoma Bar Association (OBA)
• Tulsa County Bar Association

Awards & Accolades

• Martindale-Hubbell AV Preeminent Peer Rated since 2022