Chester Crawford Insurance and Tax Services


Chester Crawford Insurance and Tax Services

Anyone who has lived in the Huntsville area for a while has likely at some point met Chester Crawford, owner of Chester Crawford Insurance and Tax Services. 

He’s been doing business here for the past 40 years. He is no stranger to the community, having been born and raised in Huntsville.  Crawford graduated from Huntsville High School in 1976. During his senior year, he was the sports editor for the school paper, The Hive; he was also class president and was voted most likely to succeed. He went on to attend college at Sam Houston State University, and he graduated with a Bachelor of Business Administration in 1980. Soon after, he began working at Huntsville National Bank as a bank teller. “I was the first black male bank teller in Huntsville. I always thought I wanted to work in banking, but that never happened,” said Crawford. While working at the bank, a man started talking to him about working as an insurance agent. Soon after, he obtained his insurance license and opened his own business in December 1981. Since then, he has been providing insurance and tax services to the Huntsville community and surrounding areas. Originally, between 1987 until 1997, his office was located at the old Bennett Building (which was located next to the current Rather Park) before moving to his current location at 100 Hwy 190 East (11th Street). 

Crawford “wears many hats” while serving the community in various capacities. He is an Independent Insurance Agent who works with various companies.  This allows Crawford to search for the best policies for his clients.  Through the years, he has been able to build trusted relationships with his clients and prospective clients through networking, word of mouth, and referrals.  His agency offers life and auto insurance, homeowners, and renters insurance. 

Additionally, he is an enrolled IRS agent and prepares tax returns for individuals, small businesses, S Corporations and partnerships. S Corps are sometimes formed when small businesses start growing. They are business entities that offer tax advantages while maintaining the flexibility of ownership.  Crawford also stated he advises clients regarding IRAs, 401k rollovers, and much more.

According to Crawford, being an enrolled IRS agent means he can represent taxpayers before the Internal Revenue Service, and being awarded the status of an enrolled agent is the highest credential presented by the IRS. This elite status comes with a great deal of responsibility to adhere to ethical standards. Enrolled agents are also required to complete 72 hours of continuing education courses every three years. Crawford is a member of the National Association of Enrolled Agents and the National Society of Tax Professionals. Both of these organizations provide year-round tax continuing education. 

As if those things weren’t enough to keep him busy, Crawford is a TitleMax Automobile Appraiser, serving Huntsville, Bryan College Station, Madisonville, and other surrounding areas. Utilizing the TitleMax App, he uploads photos of vehicles and other pertinent information from the borrower to submit to TitleMax.  They then determine a title loan amount in accordance with the value of the vehicle. Finally, Crawford also serves as a Texas Notary Public for anyone needing certification of legal documents, etc.

According to Crawford, the COVID pandemic has not adversely affected his business. In fact, it has–in many ways–improved the efficiency of how he does business with his clients. Since people do not currently feel comfortable with face-to-face visits, they have found it more convenient to correspond via emails, text messages, and some even send screen shots of documents they need to submit. All in all, he says business is doing well. 

Over the years, Crawford has been engaged with his community. Early on in his career, he coached the first championship  tee ball team in Huntsville in 1981. He was a member of the Huntsville Leadership Institute class #2 in 1983. He is an active member of the SHSU Booster Club. He was appointed by Dr. James Gaertner to the SHSU alumni board, where he served for 5 years, and is a Life Member of the SHSU Alumni Association. He has been a member of the first Greek fraternity, Alpha Phi Alpha, for 43 years. Crawford said he enjoys being a part of this fraternity because it promotes brotherhood, develops leaders, and believes in providing service to communities. It teaches men how to become better men, and it has also been a great way to make connections outside of the local community.  

“One of the advantages of working in the same town you grew up, is that you get to know a lot of people, and I know a lot of people,” he said, while nodding at the same time. A great number of them, he met during his childhood, and many others during his college years, as an adult, or through his business.  As he reminisced, he pointed out that he grew up in a house across the street from his current business site. He said, “This building was once the East End Washateria, and it was owned and built by Mr. Scott Johnson.” He remembered being about 15 or 16 years old and walking across the street and telling Mr. Johnson he wanted to own that building, and Mr. Johnson would say, “You don’t want to own this,” and he’d respond, “Yes, I do!” He said he also remembers when the old courthouse burned down, when schools were integrated in 1968, and when Martin Luther King was killed. “I was 10 when that happened.” He added that, at this stage of his life, he now knows more people who have died than people who are alive. He stated he sees that as a blessing, because it means he has been around for a long time. 

Crawford and his wife Pam live in Conroe. She is also an SHSU alum. She worked in oil and gas for 36 years and recently retired. When he’s not at work, Crawford enjoys spending time with his wife and going to church. They attend IMPACT Church of The Woodlands, the same church he and his wife have been going to since they were married 22 years ago. He is also a part of the music and worship ministry at his church. He enjoys traveling, and they have been fortunate to have visited various countries. “Two of my most favorite places have been the Vatican, because it’s breathtaking, and Pearl Harbor…it moves me, every time I go.” He also enjoys exercising and runs two miles every day. 

On a final note, Crawford reminds everyone that tax season began in January, and he is available to help you prepare and file your tax returns.  The deadline to file taxes is April 15, 2021.  If you are interested in scheduling an appointment, call 936-661-0692.


100 Highway 190 E, Huntsville, TX 77340

Phone: (936) 291-1887

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