About Michael Todd Oldfield


The healthcare insurance market is complicated. Everyone; seniors and those under sixty-five need a guy like me to help them navigate it’s complexities. I am seasoned, experienced, and VERY knowledgeable about Medicare. Plus, I love to teach. I can help anyone understand Medicare and other programs. So whether you are just now aging in or you need help with your under sixty-five, Affordable Care (ACA) plan, I invite you to give me a call or meet with me. I will be happy to do all I can to help you.

I am licensed by the Kentucky Department of Insurance and happily appointed as an appointed agent to MANY MANY OF THE BEST companies.

What I Do Best

The simpliest way to say it is; I listen, learn, and teach. I do not visit anyone with any purpose other than to learn about their case and advise them the best I can.

All types of personal health and life insurance products including life insurance, health insurance, critical care, dental, vision, fixed and indexed annuities, and long-term and home health care. I can help you save money and I can help you grow your money for retirement. And, everything in between.

HEALTHCARE: I Serve Medicare Beneficiaries

Are you on Medicare or about to be? I use Medicare’s own website; www.medicare.gov to assist me in researching every client’s case. We look together to find the least cost route to take that will provide beneficiaries with the best protection given their individual needs. There is no better resource than Medicare for this information.ACA Quote Page

Marketplace (“ACA”) For Those Under 65 Years of Age and Not on Medicare

Our company, the Cool Insurance Group, LLC has established our own healthcare exchange platform to assist you in your Affordable Care Act plan. The features and functionality very closely resemble the former Kynect.com which was eliminated in Kentucky at the end of 2016. I offer my assistance in helping you navigate and explore all your healthcare options in this rapidly changing market.

Working together we can find out ALL you are eligible for and help you take advantage of all subsidies to make your healthcare insurance costs the lowest possible.

ACA is not the only item “under 65’s” need to concern themselves with however. We need to have thoughtful discussions on the topics of life insurance, estate planning, critical care, and of course “long-term” case planning and suitability.


MEDICAID: For those who are struggling and need some help, I am happy to help you get set up with our Medicaid system through the state. Call me and we will do it together.


LIFE INSURANCE – Term & Whole Life Insurance

Final Expense

Morgage Protection

Debt Elimination For EVERYONE That Has Debts

Did you know that there is a way to get rid of all your debt; including your mortgage? It’s takes less than nine years. The good news is that most people do not see their monthly budget change while doing it. That’s right, you may not have to spend a nickel more to do this. AND, it’s all guaranteed. Now, is that not worth a conversation?

Please give me a call at 859.654.0120 extension 1001 or drop me an email to toldfield@coolinsurancegroup.com and I will be happy to reply.

Next – More Information

Real Client Testimonials

Read what a bunch of people say about the work I do.

John M.

Todd has given me excellent service for 3 years.

Clara Q.

You have always been there for me. You explain y options so that I could understand. You have baan a friend to me and I appreciate you.

Edna S.

Saved me money on my health insurance premium. Helped me file forms for GTL insurance.

Shelby C.

Go me connected!

Karen S.

My husband and I started with Todd after we decided not to go back to Winchester to an agent. Todd has been wonderful with us. He cares and makes sure you get what is best for your needs.

Would not have anyone else but Todd.

Wayne S.

Todd opened my eyes on opportunities for my retirement savings as well as my options for my healthcare. Plus, he's fun!

D.A. Ball

Todd helped me by coming to the house due to my fall and I cannot walk.

Carolyn C.

I attended a class. Todd helped me with my Medicare & savings!

T. Bruner

Todd has always been there for me no matter what I needed help with. He is a very updated and knowledgeable agent. He is very nice and helpful even if he has to drive a long ways to get to you.

Thank you Todd

Vicki B.

Todd came to my house and I felt he and I had known each other for years. He showed me how I could save and believe me, I have saved!

I love Todd!

Stephanie S.

Even though I had years of medical insurance billing experience, Todd help me navigate the Medicare options that were the most financially beneficial for me and my current situation.

I trust Todd and appreciate his knowledge and sensitivity to people on fixed income.

Stephanie S

Virginia Y.

He got me some relieve of prescriptions.

Dennice L.

Helped me with my Medicare and recommended additional supplement for future coverage.

Ronald B.

You cost me money. You at all my chili but you licked the bowl clean HO HO!

Pamela W.

Saved me money - I feel better knowing I have more coverage -


Mr. Todd is a good person - is willing to take time to help you in all your needs.

Marion S.

Todd helped me to get an Anthem Advantage Part D Plan. It is working fine but I want to add eye and dental. I know Todd will help me with that too. I am very satisfied with Todd Oldfield,

Pauline R.

My out of pocked expenses have been minimal!


Todd has always been available any time I have questions. He has helped friends of mine with good coverage as well.

Joe E

Todd helped me with my Medicare.

Amy E.

Todd helped me save money on my healthcare

Richard & Mary C.

Todd did all the leg work to get the most for the least. For me, it saved me a tremendous amount of time and frustration.

James T.

You saved me money on my insurance.

Mary C.

You save me money on my healthcare now that I have had a pace maker. I had it put in February of this year.

Janet R.

Todd has put up with me and I really appreciate it. Thank you, Todd!

Lillie N.

Todd is an excellent man & sure is intelligent person. God Bless him.


Elizabeth D.

Todd helped me navigate the crazy world of Medicare and I would be lost without his knowledge and expertise.

Janet R

Very well & God Bless You.

Frances J.

I want to thank Todd for suggesting that I purchase a supplemental insurance ("GTL"). I had a bad fall and broke both shoulders. Without the insurance, I would have had more co-pays.

Thank you, Todd.

Mario S.

Todd helped me get an insurance plan that saved me almost $300. Also I can get OTC drugs.

Pamela W.

More coverage. Less money. I now have peace of mind.

Nada T.

Todd is an awesome person that has taken care of me for the last few years. Love the personal detail and with a fine tooth not missing a beat with my Medicare needs. Has helped me one on one and he is very unique and one of a kind.

Jerry M.

Yes. Save money on my insurance by using a better plan.

Nathan G.

I have been so please with Todd. I have been working with him for 4 years. Always does a great job checking each year! Always asking all the questions to see if my needs have changed.!

He is the real deal!

Norma H.


John W.

I trust Michael Oldfield. He's been my agent for years. He always makes time for me. Always makes time over the year to explain any changes. If I have any questions, I can call him. If he's not available, he calls me back soon as he can. I probably would have changed a long time ago if Mr. Oldfield wasn't my agent. He's like family.



...I want to hank you SO much for guiding me into a supplemental insurance policy. I have had a really rough year, health wise.

In September last year, I got a fracture in my lower back. In December I got another one. I went through therapy, shots, etc. Long story short, I had surgery on July 10th. He put rods and screws in and I am doing better with that. Still in some pain, but considering the excruciating pain that I was in, I hate to even call it pain.

I have had pain and weakness in my left leg since the surgery. He thinks I have a pinched nerve or a damaged nerve above where he put the rods in and he is still working on this problem.

Again, thank you for all you have done for me. If it wasn't for the supplemental insurance, I could not have had any of this done. I have been to more doctors and have done more procedures done this past year than I have in my entire life combined. That includes going to my doctor every 3 months for my diabetes (which is doing great). 

I know my insurance premium will probably skyrocket, but I am so blessed to have had a way to get this done...

Very sincerely.


K. M. Bell

Todd helped me pick a plan that best covered my needs.

D. Todd

Saved me money on not having to pay monthly premiums and on prescriptions (by receiving them in the mail.)

Saved me more than $2,000.00 per year.


A. Clark

Todd saved me a specific amount of money.

Todd increased my coverage.

Todd gave me information for different plans & price & how to use them to my benefit.

Thanks Todd

Chris C.

He helped me find the proper health care coverage for me.

Mavis C.

Saves me money.

Larry E.

Yes. You sure have saved me and Phyllis lots of money and hope to keep saving.


Ron B.

Yes, we feel you have helped us. Fortunately I have had no measure illness.

Christa J.

Mr. Todd has been of great professional assistance for our Humana Medicare insurance.

Bonnie S

Saved on prescriptions.

Nada TJ

My cool agent Todd is an amazing, great thorough and knowledgeable man and has the personality to go with it.

J. Curtis

Todd was a great help to me this past year on a claim for me. Found out Medicare or Humana didn't pay for a chair lift for our home. He will answer any questions I have for him. Thanks Todd

T. Bruner






Barbara B.

Todd helped me with advice on a long-term care policy that I have had for years never used but it, was changed and the cost went up, and services afforded went down. I feel his advice was the best I could have found and was available. He is a special man devoted to his clients. He helped willingly and it meant nothing to him or his time.

Beverly C.

Todd explained things to me so I could understand it. He pointed out this policy that world be the one better to save me money.

Jerry M.

Todd helped me get my insurance cheaper.

Nathan G.

Todd is very specific -- cutting to the chase - helping save money on healthcare and it great! And fast!

Pamela H.

Todd has always helped me in finding more reasonable prescriptions within the area.

NMT Johnson

Todd was very detailed and covered my every need.

Very nice, trustworthy as well. Honest in explanation and knowledgeable about what he was talking about.

Ron L.

Knowing that Cool has my back is a advantage.

Larry E.

Todd helps all around.

Bill F.

Mr. Todd came to me on a day's notice, and advised me of my options and helped me chose the plan that best suited me. He is great at his job and very knowledgeable of your choices. I would recommend him to anyone because I have to my own family members. I am also proud to call him a friend.

Minnie C.

I would be lost without Todd.

Shirley W.

Todd has always been very helpful. He explained thoroughly the plans available and which would suit my needs better. On top of that he's always been very friendly and has a good personality.

Dennice L.

Todd told me about OTC plan (vitamins, etc.) that I was not aware of. Saves me at least $45 per calendar quarter. Every $$$ counts. Very pleasant to work with.

Marion S.

Todd helped me on my medical prescriptions with lower prices for me to pay.

Denny & B. L.

Dear Todd Oldfield;

We were very pleased to of found someone we can rely on that will return calls if needed and always with sincere humor always ready to answer our questions. We feel you saved us money and did not increase our premiums. That's a plus! We love doing business with you. Hope to always have you around. Stay cool. Sincerely.

Mary C.

Todd help me save on Medicare and healthcare.


He was very nice and helpful to make us understand our plan more completely. He saved us money also!

Christa J.

Todd Oldfield has been very helpful in regards to our health insurance and has been very dependable.

Bonnie S.

Todd was extremely helpful with my Medicare intitial application for prescription coverage. Todd returned twice to ge everything just right. I learned cheaper isn't always better.

Thanks, Todd




Todd saved me money on my prescriptions. I love the Silver Sneakers program.

Maureen B.

Todd helped me save money and was really good with the paperwork. He showed me all my options.

Regina F.

He helped know which was the best way to go on my insurance. Then last year he helped me get some bills cleared up through my insurance after a surgery.

He was kind, patient with me, and wonderfully helpful.

Beverly C.

Todd helped me pick out the right package for me. He explained everything to us so we understood it. Very nice and well mannered.

Jerry M.

Yes. Todd helped me save money on my prescriptions and health care.

Larry Joe

You have saved us money. Hope you can keep saving us money. Lots of the medicine is a racket. Thanks for being there for us.

N. Hampton

Todd helped me very much. He answered all of my questions.

Ron B.

Calmed my fears. The plans you picked for me worked great. Thanks.

Lillie N.

Todd helped me with answers when I need help. Thanks a lot!

Skip S.

Todd helped me transfer to Humana without any problems.

Phyllis S.

Todd showed us an insurance plan that was right for us. The process was quick, simple, stress free,  no-hassle. Amazing! God Bless you and thank you!

Gary M.

Yes. It saves me money!

Gladys R.

Helped me know what I needed. Very kind and helpful.

Pauline R.

Anytime I've had questions Todd has always took the time to explain what I need. With health insurance as it is today, we need someone to "stand in the gap" for us. Todd is not only our agent but has become a dear friend as well. Really do appreciate him.

Mary C.

You helped me understand my healthcare and my Medicare. Thank you.

Nelson G.

Todd was good about meeting me at a location closer to where I live.

Wayne C.

Thanks for helping me get my meds!

An for all the trouble you have gone though trying to get my Medicare Part B straightened out. See you soon.

Ruby G.

Todd saved me money when he explained the benefit of an HMO instead of the PPO I had for years. Given my good health status I do not go to the doctors much. Todd also looked up different PCPs for me to choose from. Very helpful. I have never had this much help!

Larry E. & Phyllis J.

Todd saved us money on insurance, Medicare and he can answer all your questions.

Shirley W.

Todd helped me get set up with Humana Advantage plan. He made it easy and I greatly appreciated that.

Marion S.

Todd helped me save $18.80 on my prescription medications.

Phyllis D.

Mr. Oldfield helped my husband and I get his retirement plan plus social security for us in order. Had I listened better, I would be paying less for a drug plan.

R. & J. Brandenburg

Todd, You saved us money and we were so happy I ran into you at Wal-Mart. We found you to be a really nice quy and look forward to working with you next year. I will make you chili again!


Jennifer P.

Todd found me the best plan with the most options for less money. Explained in detail the various components of my policy and how to save money.

P. Rhineheimer

Todd has always been very helpful in answering any questions I have had. Has also helped other family and friends.

L. Braddock

The most helpful agent ever.

M. Warren

Very Informative!

Christy R.

Todd was an absolutely wonderful in helping us to navigate our way through the medicare and supplemental insurance hurdles. He took the time to explain everything for us and was very knowledgeable. I would highly recommend him.

Dave G. aka Riverdave

I was very impressed by the excellent meeting I had with agent Todd Oldfield from the 'cool' group of agents. He was very through, professional and knowledgeable. He had the answer to any question I had and further was not in a rush, seemed like he thought I was a human being as opposed to just another commission. He also met me at a little deli about half way between Lexington and my little home down on the Kentucky River. [to tell you the truth I believe he would have come all the to my home but I would not ask that of anyone without a 4 wheel drive vehicle that had a ground clearance of at least 10 inches. But I bet he would have . ]

If the rest of the agents associated with the 'Cool Group' are anywhere near the caliper of Mr Oldfield then this is certainly the place to shop for your insurance needs. In my case I was to start with Medicare. (the government seemed pretty adamant on this point) The plan Mr Oldfield laid out was with Humana and I truly believe that I came out with better than I could have by just letting the government give me whatever their concept of health-care is, the Humana folks picked up from there and sent me a great deal of info on my plan and continue to be on call for any questions I may have.


Now I just need to get sick. OK, no I really do not want to get sick, but it's a comfort to know that I have good coverage and then some. I did book an appointment for a check-up and place an order for my monthly $30. worth of over the counter items including a blood pressure cuff w/stethoscope.
I highly recommend the 'cool' group and agent Todd Oldfield.

Yours in Liberty,
David G. aka riverdave

C. Baker

Todd came to my house instead of me having to go to him. He sat down and explained Medicare and supplemental health insurance fully. Through his computer program he defined best program for me. Additionally best RX program and saved me ENORMOUS time and energy.

"Best insurance agent I have dealt with."


Rita H.

He is very knowledgeable, with insurance needs very helpful. If he does not know the answers he will gladly find out and get back with his client. I like his work ethics. Nice. Polite.

Pauline R.

Todd has always explained the choices well. He has been available anytime I or friends of mine had questions or issues about payments. He has become a friend.

Melvin S.

Mike (Todd) was extremely helpful with my insurance coverage. I feel he got me the best possible insurance and at the least cost! Very, very knowledgeable.

Robert S.

My agent, Todd Oldfield was very professional and very well informed.

J. Martin & L. Harper

Mr. Oldfield came to our home and explained the choices of supplements. He was very knowledgeable and patent when we asked questions and I feel I can call him anytime if questions arise.

D Whitt

I want to thank Todd for making a big difference in my life. Since I am turning 65 soon, Todd came to my home and reviewed my current insurance. I am thoroughly confused by insurance companies. Todd showed me that I have been paying $60 a month, for the past 6 years for a policy that has covered nothing. Todd made phone calls and prepared the necessary paperwork while he was at my home. Now I have the coverage I need, extra money each month, and Todd as my agent to make sure my insurance needs are met. He is also very friendly and by the time he left, I felt like we were old friends. Thanks Todd!!

D. Dickerson

You surely must know you are appreciated by all your clients. The labyrinth of insurance details is messy business. A person needs people like you to sort out the messy, confusing options. Aside from making an informed choice, you were especially pleasant and kind.

Michael L.

The speaker clearly knows the material. I came away feeling like I had a much better understanding of Medicare; it's components, my exposure to financial risk should I become ill, and how to protect my finances.


Michael Todd is one of a dying breed of sales reps. He knows his product , is very sincere and honest and as dependable as a mother. He loves his job and strives to be the best for you; the customer .