Rachael Brennan has been working in the insurance industry since 2006 when she began working as a licensed insurance representative for 21st Century Insurance, during which time she earned her Property and Casualty license in all 50 states. After several years she expanded her insurance expertise, earning her license in Health and AD&D insurance as well. She has worked for small health insuran...

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Chris Harrigan has an economic degree from Limestone College and an MBA from Clemson University. He previously managed auto insurance claims for Enterprise Rent-A-Car. Currently, he is using his business and insurance expertise to provide insurance data analysis and visualizations to enhance the user experience.

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Reviewed by Chris Harrigan
Former Auto Insurance Claims Manager

UPDATED: Aug 12, 2021

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Key takeaways...

  • Charter Oak was founded over 120 years ago in Massachusetts
  • Charter Oak provides businesses, individuals, and families various types of insurance products
  • Charter Oak also offers policies for commercial car insurance and other policies for businesses

The Charter Oak Car Insurance review is a review of the Charter Oak Insurance and Financial Services Company. Charter Oak was founded over 120 years ago in Massachusetts.

Today, Charter Oak operates mainly out of the Northeast United States and has over 70,000 clients.

Charter Oak has over two hundred professionals that work to make Charter Oak a leading insurance provider. Charter Oak is a subsidiary of Massachusetts Mutual Life Insurance Company and one of their largest companies.

Charter Oak has over $3 billion in client account values and more than $11 billion in life insurance coverage in force.

Just enter your zip code above to compare car insurance quotes where you live!

What does Charter Oak provide?

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Charter Oak provides businesses, individuals, and families in the Northeaster United States with investment services, retirement planning, business planning, risk management products, business protection, and financial planning.

Some of the personal services that Charter Oak offers include:

  • Life insurance policy
  • Long-term care insurance policy
  • Disability income insurance
  • Estate and trust analysis
  • Retirement investments
  • College funding programs
  • Securities brokerage services
  • Wealth transfer funding and design

Charter Oak also offers policies for commercial car insurance and other policies for businesses.

These business products include executive fringe benefits, business planning and protection, employee benefits programs, business overhead expense insurance, and business succession and buy and sell agreements.

Charter Oak does not offer personal lines of car insurance, but there are many national leading companies in your area that do.

To see a side-by-side comparison of these companies car insurance rates for FREE, enter your zip code below to get started!


  1. https://www.investopedia.com/investing/
  2. https://www.metlife.com/insurance/life-insurance/
  3. https://nahu.org/looking-for-an-agent/helpful-guides/consumer-guide-to-disability-income-insurance