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Hale Stewart

Hale Stewart

Hale Stewart is a captive insurance expert and a tax attorney. His clients range the gamut from high net worth individuals who utilize one or all of his estate planning, asset protection or captive insurance skills, to small companies forming a captive, to larger associations looking to lower their insurance costs.

Before law school, Mr. Stewart was a bond broker with Vining Sparks, where his clients were comprised of mutual funds, insurance companies and money managers.  He returned to law school in 2001, graduating from the South Texas School of Law in 2003.  After law school, he opened his law practice focusing on transactional work.  He continued his education at the Thomas Jefferson School of Law in 2007 where he obtained an LLM in domestic and international taxation,  graduating Magna Cum Laude.  He has three certifications from the American Academy of Financial Management: Chartered Trust and Estate Planner, Chartered Wealth Manager and Chartered Asset Manager.  He is the author of the book U.S. Captive Insurance Law and is currently working on his Ph.D..  Mr. Stewart also practices in the area of asset protection and estate planning law.

Recent Articles by Hale Stewart

There Are No Rules For Dealing With Those Who Suffer From Some Type Of Dementia

Let me begin by saying: There are no rules for dealing with this. That is, there is no firm set of steps to take, no one size fits all plan. Sometime over the last few years, the baby boomers started to retire. This has created a complex double-edged sword for professionals. While these people are […]

The Ten Questions of Captive Insurance, Part 3

This is the third and final installment in a three-part series of articles on the ten questions all prospective captive owners should ask themselves (or, that their financial representatives should ask them) to help in the captive formation decision making process. Part 1 in the series can be found here, and Part 2 can be […]

The Ten Questions Of Captive Insurance, Part 2

This is the second installment in a three-part series of articles on the ten questions all prospective captive owners should ask themselves (or, that their financial representatives should ask them) to help in the captive formation decision making process. Part 1 in the series can be found here, and Part 3 can be found here. […]

The Ten Questions of Captive Insurance, Part 1

This is the first in a three-part series of articles on the ten questions all prospective captive owners should ask themselves (or, that their financial representatives should ask them) to help in the captive formation decision making process. Part 2 can be found here, and Part 3 can be found here. Forming a captive insurance […]

The Flood Plain Cases, Part 1

Although we think that the first important legal battle for captive insurance occurred during the economic substance cases that started in the 1970s, the reality is two cases from the 1950s (US. v. Weber and Consumers Oil Corp v. US) have all the hallmarks of modern-day captive insurance programs. Most importantly, at their conclusion, these […]

The IRS And Captive Insurance

Starting in the mid-1970s, and continuing through the UPS case, the IRS fought captives tooth and nail. Over the course of these cases, they advanced three different legal arguments against captive insurance: the economic family argument, the nexus of contracts and the assignment of income doctrine. However, it’s important to ask this question regarding the […]

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