About Us


Our Professional Team


  • Jack W. Bolling, Esq. - Lead Attorney
  • Amanda B. McAlear, Trust Funding Manager

Jack received his Juris Doctor from Michigan State University College of Law, and his bachelor’s degree in business administration from Michigan State University and William Tyndale College.

Before becoming an attorney, Jack was a VP National Accounts and VP/General Manager working at companies such as Georgia-Pacific, ADVO, Mead Corp., Alco-Standard, and International Paper. Before that he was in law enforcement for 12 years, after brief service in the USMC. Jack also teaches Political Science and Criminal Justice at Schoolcraft College.

Elaine and Jack have been married 47 years and have been residents of the Milford area since 1978. They have 3 children. Their daughter, now a stay at home mom, was formerly in management with a Microsoft affiliate in Chicago.

Their sons are also lawyers. One son owns and operates The Bolling Law Group, PLLC. His practice focuses on family law, criminal defense, social security disability claims, and general civil law, and offers Jack's client families a full-service legal option. Plus, he is very active in youth sports coaching and administration.

Their eldest son is a U.S. Marine Corps Lt. Colonel, and a United States Navy and Marine Corps Court of Criminal Appeals Judge. He is also senior litigation counsel at the Thomas More Law Center whose mission is to: preserve America’s Judeo-Christian heritage; defend the religious freedom of Christians; restore time-honored moral and family values; protect the sanctity of human life; promote a strong national defense and a free and sovereign United States of America.

Jack is a member of: the prestigious National Network of Estate Planning Attorneys; the National Academy of Elder Law Attorneys; the American Bar Association; the Master Lawyers Section of the Michigan Bar Association and its Probate, Estate Planning, and Elder Law sections; the Michigan Institute for Continuing Legal Education estate planning/probate certificate recipient; the American Legion and the Marine Corps League; and he is past President of the Michigan Forum of Estate Planners and Michigan Conference of Estate Planning Attorneys and a past advisor and speaker for the Red Cross/Family Care-giving and Fifty-Plus Advisory Committee at Schoolcraft College.

Jack is a guest columnist for Gannett Newspapers writing about estate planning and related subjects, and a speaker on these and related topics nationally.

Jack is an active contributor to his community, including the Boards of Directors of the Huron Valley Chamber of Commerce and the Carl’s Family YMCA of Milford. He volunteers at the Wixom, Highland, Commerce, Dublin, and Milford Senior centers, and is the founder of the “Ask the Attorney” programs at Dublin, Wixom, and Milford Senior Centers. Jack has many years in youth athletics, coaching and administration, and was liaison to the Youth Sports Institute at Michigan State University.

Jack’s law office is located at 1550 N. Milford Rd. Suite 204, Milford, MI 48381. His practice focuses on estate planning, Medicaid and Elder Law, trust and will (probate) estate settlement, social security disability, and he is an accredited attorney with the VA for veteran’s benefits.

Born and raised in the Huron Valley Community, Amanda is a resident of Milford. She was most recently employed at Farm Bureau Insurance working as an Account Specialist. She started her career at DaimlerChrysler Financial Services after graduating from Central Michigan University with a Bachelor of Science degree.

Amanda is married with 2 children. She volunteers at St. Mary’s Catholic Church, Johnson Elementary and also helps out when needed at her family's local restaurants; Baker's of Milford, Highland's Comeback Inn and the South Lyon Hotel. Amanda enjoys spending time with family and friends, traveling and working out. Amanda has run several marathons and half-marathons!



Legacy LifeLines

Our unique approach to estate planning


An avid history buff, Milford attorney Jack W. Bolling is passionate about keeping the past alive for future generations. He is just as interested in preserving your family's legacy by helping you make decisions that will keep your memory alive through your children and grandchildren. With a deep respect and passion for history, Bolling is pleased that his practice can help families see their past and plan their future. "History comes alive to me while conducting my practice and learning about my client families," Bolling said. "It gives me a sense of the past and a vision for the future - exactly what I want to bring to my clients."

Jack has trademarked his approach to the estate planning process and accompanying legal services as Legacy LifeLines™. His unique process consists of three steps:

  • Personalized, individual counseling and plan design. Not just filling out forms!
  • Important funding of the revocable living trust. If your assets aren’t owned correctly your estate plan will fail!
  • Lastly, an on-going client update and maintenance plan that is unique to Jack's practice.

Jack encourages his clients to think beyond their financial matters and look into their own life's fulfillment by asking themselves questions like: What and who really matters most to me? What legacy do I really want to leave behind? "Through proper planning, it is possible to provide for your long-term care while preserving assets for you and your loved ones," Bolling said. "Why should you give up what you've worked your whole life for just because you or your spouse becomes ill?" These important life questions are all the more reason that Bolling expanded his practice to include Medicaid and VA planning, and he helps families with trust and probate estate settlement.


legacy lifelines at Jack W Bolling Law Office