Shane Kelley’s story presents an interesting study in contradiction. Trained by his father who was, in turn, trained by his father, Kelley joined the highly successful family trusts and estates firm in Fort Lauderdale right out of law school and has worked there ever since. Coming from a family of lawyers, some of whom practice together and all of whom have remained in close proximity to one another, the Kelley family illustrates an unusual legacy of close-knit professionalism. It is in comparing the strong ties that exemplify the Kelley family to their trusts and estates practice that the contradiction becomes apparent. The dissolution of the traditional family model is what drives much of Kelley’s practice: seniors distanced from their children subjected to the predatory conduct of strangers, multiple marriages leading to distrust and alienation amongst children, corrupt fiduciaries, and philandering spouses. Add to this mix some very high-profile names and cases, such as Edna Winston and Anna Nicole Smith, and you have a good insight into the diversity and challenges posed by Kelley’s practice.

Kelley graduated from the University of Colorado at Boulder. He earned his JD from Stetson University College of Law and earned an LLM in taxation from the University of Florida, College of Law-Graduate Tax Program. Kelley is board-certified by The Florida Bar as a wills, trusts and estates lawyer. He is a member and past chairman of the Probate Rules Committee of The Florida Bar. He is also a fellow of The American College of Trust and Estate Counsel, a national organization of experts in the field of estate planning and probate law.

Clare Cosslett: How did your family come to Florida?

Shane Kelley: My family originally came from Oklahoma during the Dust Bowl. When they arrived in Florida, Fort Lauderdale was little more than a trading post. It was still part of Miami-Dade County. They put down their roots here in Fort Lauderdale and the family has been here ever since Charles Everett Farrington, my great-grandfather, became the third mayor of Fort Lauderdale. He helped to incorporate Broward County. My great-aunt, on the Farrington side, was one of the first women in the state to go to law school. Stetson Law School was the first law school in the state of Florida and she was one of the first women to graduate. My father’s uncle was a judge here for a very long time, Judge Farrington. One of his children worked for Janet Reno in the Justice Department. And out of my generation, three out of five of us are now lawyers. My twin brother is a lawyer up in St. Augustine and my sister is in Tampa.

Cosslett: That’s quite a family lineage . You have two generations of Kelleys currently practicing?

Kelley: My father practiced with my grandfather until he passed away in 1977, and he then continued the practice. I joined in 1995. We have two partners.

Cosslett: What is it like to practice law with a close family member?

Kelley: It’s nice to be in a family business. I graduated law school in ’95 and I’ve been practicing with my father ever since. I don’t know that a law practice is any different than any other family business. When I graduated law school, the first case I worked on was the Edna Winston estate. My dad took me to every hearing and let me attend every deposition. He wasn’t worried about me getting billable hours. If I had gone to a big firm, they would have said, “You need two thousand billable hours. Go get them.” Billable hours didn’t matter to my dad. He was trying to make me the best lawyer I could be. I got a jumpstart on being a litigation attorney . It was a great benefit to me.

Cosslett: It sounds like it is beneficial for a young lawyer to train in a smaller firm that doesn’t have billable-hours requirements and perhaps has different priorities.

Kelley: I spent some time practicing with Holland & Knight here in Florida and they have some great lawyers there, but it depends on how firms are going to develop their associates. It varies firm by firm, but certainly, if you have a smaller firm where you have the freedom to focus on training, then it can be beneficial as long as you have the resources within the smaller firm to really train someone.

Cosslett: Especially when it’s your dad and he has a vested interest in making sure that you learn what you need to. Has the family practice always been in trusts and estates ?

Kelley: My father used to do some real estate, which was what my grandfather did, and then when he went to practice on his own, he changed it exclusively to trusts and estates law, and that’s what he’s been doing for twenty-five years.

Cosslett: When you were growing up, was it always assumed that you would join the family practice?

Kelley: It was always an option. I didn’t always want to be an attorney. I really wanted to attend graduate school and be a professor, either English or history. When I graduated college, I had to make a decision, and I decided to attend law school. Practicing law was the family business, and it sounded interesting. I thought that was the best route to take at the time, and it’s worked out great for me. I enjoy doing what I do, so I can’t say I regret my decision.

Cosslett: Why did you go to Stetson?

Kelley: Well, my sister was going there and my father was a friend of the dean at the time. My twin brother went there also. It’s a good law school. It’s in Florida, and I wanted to come back to Florida since I was going to practice here. It was a good choice for me. I ended up going straight through and went both summers so I could graduate a semester early. At the time I thought, “I want to get out of school and get to work.” Little did I know how great I had it in school! I loved law school.

While I knew I was going into trusts and estates law , I only took one class in trusts and estates because they just didn’t have the classes available. Trusts and estates was a very popular class and the third-year law students were the only ones who could get into it. The only tax class I took was basic income tax, so I really wasn’t exposed to trusts and estates or tax when I was in law school. I really loved constitutional law. And actually, it sounds weird, but I really liked labor law. I took advanced evidence, and trial techniques, those kinds of things.

Cosslett: Did you have any internships ?

Kelley: I worked from my second year on. I always had a job. At first, I worked as a clerk at a law firm. And then I clerked for a year for a really great probate judge, Thomas Penick. He has since retired. The three of us, first my sister, then myself, and then my brother, were his clerks one after the other. He was an excellent judge. He let us sit in on all the hearings. We did research for him, and were able to discuss which way he ruled on those issues and why. He let us into the process. It was very valuable.

Because he thought it was important, the Judge took us on what they call Baker Act hearings, which is where someone is being involuntarily committed because they’re a danger to themselves as a result of drug use or mental issues. He said, “It’s important that you get to see that people’s rights are being affected here.” People could be involuntarily committed on the basis of the hearing. I received a very thorough background into every aspect of probate law. In Florida, probate courts handle guardianship and Baker Acts and those types of things.

The last semester of law school I interned with the state attorney. They have a program where students are temporarily admitted to practice law on a limited basis, and they let me handle misdemeanor cases. I think I had three DUIs and a couple of batteries. They’d have a state attorney work with you and say, “Okay, you can do the opening, you can do the direct on certain witnesses.” They’d give you certain parts to do. I loved it. The only trial I lost was a domestic violence where the alleged victim didn’t show up.

Cosslett: After you graduated in ’95, you practiced for about three years, and then went on to get your LLM in tax at the University of Florida College of Law.

Kelley: When I began practicing , I did simple estate planning, estate trust administration, and estate trust litigation, so I was really doing the whole gamut. I was interested in doing more sophisticated estate planning and tax planning and I wanted to become more proficient in those areas. My twin brother and I went to college together at the University of Colorado, but he was an accounting major (which was a five-year degree), so he was a year behind me in law school. When he graduated, he went straight into the LLM program. When he came out, I said, “I’d like to go into the program,” so he could come in and fill my spot in the office. I then went to do the LLM. It was a very intense one-year program leading to a master’s degree.

Obtaining an LLM was one of the best things I’ve done. The experience was so beneficial to my practice. It was a different world from my law school experience. And the program at Florida is very good. NYU is the number one LLM program in the country, and then Florida is ranked number two. It’s a very good experience and I would recommend it highly to anyone who wants to get involved in any type of estate planning.

Additionally, when I graduated the LLM program, I was courted—firms were flying in to hire LLMs. That was back when the big accounting companies, Ernst & Young and KPMG, were stockpiling tax attorneys because the firms were trying to become multidisciplinary firms. They wanted to do the estate planning as well as accounting. In Europe, the big accounting firms are the biggest estate planning firms because they’re allowed to have a multidisciplinary practice over there. The biggest tax firms do the planning for their clients. They tried to establish that model here, but the ABA, to their credit, fought that very hard, and the accounting firms never progressed on that issue. But I remember they were just plucking people out of the LLM program in the hope that they were going to be able to do in-house estate planning.

Cosslett: On top of a large law school debt burden, adding the cost of an LLM can be prohibitive for some. Perhaps it is a good idea to do what you did, and practice a few years, trim that debt a bit, and then go out and hone your expertise.

Kelley: Yes, I went on a scholarship, but I understand. That’s why people go to Florida for their LLM instead of NYU. It’s a lot cheaper. The tuition at NYU and the cost of living in New York are both very expensive. Florida is a fraction of the price. While NYU is the more prestigious of the two schools, Florida is a very good program at a fraction of the cost. If you want to work in Florida, having an LLM from the University of Florida is very advantageous.

Cosslett: I notice you are board-certified. What does that mean?

Kelley: In Florida they have programs in which you can become certified in certain areas of the law and one of those areas is probate, trusts and estates. You take a certification test and, if you pass, then you can become board-­certified in that area. I think other states have certifications as well, but Florida’s is pretty large. Certification is supposed to signify to the public that this person has ex­pertise in the area in which they’re certified. It is a useful tool for a public who has no other way of knowing about a lawyer’s field of expertise. It’s like when you go to the doctor. How do you know that the orthopedist you’re choosing is a good one? You have no way to judge other than what people say, referrals, and you look for board certification .

Cosslett: How has South Florida changed over the years and how is your practice different from your father’s practice or your grandfather’s practice?

Kelley: My practice is actually very similar to my father’s in that he also does some estate planning, some administration, and some litigation. In that facet we’re the same. I get more involved in some of the tax issues. It used to be that our clients were almost exclusively elderly people who came to Florida to retire and they would redo their estate plan upon becoming a Florida resident. And then we would do the estate and trust administration. These days I’m seeing a lot more people who are younger, who have either lived here for a long time or who were born here. We are also seeing more entrepreneurs. Our clients’ needs are different than they used to be and, quite frankly, litigation is really what drives a practice these days. There’s a lot of trust and estate litigation and I only see it increasing as we move forward.

Cosslett: What is driving that litigation ?

Kelley: Especially down here in South Florida, you really don’t have the nuclear family model. It’s not Mom and Dad who have been married for thirty years and everyone is unified in the goals of the family. It’s second, third, and fourth marriages. Families are fighting. There’s also a lot of fraud when it comes to our elderly people because many of them are down here while their families are up North. No one’s here to watch out for them, and there are a lot of people taking advantage of them. I’m talking about outsiders—neighbors, nurses, or anyone who understands that these people are vulnerable. They get close to elderly people and either they’re getting wills or trusts done, they’re outright stealing the assets, or they’re establishing joint accounts—you name it. Taking advantage of the elderly is a cottage industry down here in South Florida. The Florida Department of Children and Families is supposed to look out for them, but there’s a huge population and not a lot of resources.

Cosslett: Has your practice been affected at all by the roller coaster in the financial markets ?

Kelley: It affects the type of cases we see and the different causes of action that people want to bring. When you have financial issues that crop up, you have more cases involving breach of fiduciary duty. Everyone wants to sue the trustee because they lost money in the stock market. Litigation is not adversely affected by the economy. If anything, it’s spurred on by a bad economy because people are motivated to sue each other. You see an increase in litigation when the economy goes down.

Cosslett: Who do you generally represent? The trustee? The individual litigants? Whoever walks into your office first?

Kelley: It really depends. We’ll defend the fiduciaries or we’ll represent the aggrieved beneficiaries. In a will contest or a trust contest, we’ll either defend the fiduciary against a challenge to a document or bring an action to challenge a document. We represent people in fiduciary litigation . We don’t really choose one side or the other. It’s whatever case is better and whoever comes in.

Cosslett: How big is the trusts and estates bar in South Florida?

Kelley: Very big. We are part of the RPPTL section of the bar. They call it “reptile” because it’s real property, probate, and trust law. We have over ten thousand members. We’re the largest and best organized section of The Florida Bar. We have an excellent organization, and our legislation is very successful. And, obviously, with a large elderly population, it’s an important area of the law down here.

Cosslett: There was a period of time where you and your dad and one of the firm partners joined Holland & Knight to develop that firm’s fiduciary litigation practice in South Florida. How big were they at the time, and why did you make that move?

Kelley: They were the twelfth largest firm in the country at the time and while there were several trust and estate attorneys, there were only one or two lawyers who were doing fiduciary litigation in Florida. They had a lot of planning and administration lawyers. Fiduciary litigation lawyers are a small community. There are not a lot of people that do it, and the people that do it full-time all know each other. The fiduciary litigators at Holland & Knight were great and we had been talking to them for a while and decided that we would go over there on a two-year basis and see how it worked out. We just picked up our firm and moved it over to Holland & Knight for those two years.

Cosslett: How was it to work for a larger firm ?

Kelley: Obviously it was different than my experience here, but there are positives and negatives. I actually enjoyed it because I was just a lawyer there. That’s all I had to worry about. I didn’t have to worry about: “Is the copier working? Do I need to look at the books today? Do I need to get taxes done?” The downside of being in a small firm is you’re not as productive because you have to do everything. You are running the office and being a lawyer.

At Holland & Knight, all I had to worry about was practicing law, so that was a positive for me. My practice was different because I did a lot more defense of corporate fiduciaries when they’d get sued for breach of fiduciary duty, or for some other reason. The clients I had were different and the negatives were, as with any big firm, that there was a bureaucracy that you don’t have in a small firm. I have an eleven-year-old daughter. If I don’t want to come to work one day, I don’t come to work, and no one’s asking me where I am and what I’m working on.

In a large firm, it’s more structured. It’s a business and they have to run it like a business. That was a lot different than what we are doing here. At the end of the two years, we decided we were more suited to being a boutique smaller firm and, because what we do is unique, I think it’s very well suited to a boutique setting.

Cosslett: Are Fort Lauderdale and Miami interrelated in terms of the population and the issues that come up or are they discrete?

Kelley: We practice in all three counties: Palm Beach, Broward, and Miami-Dade. They’re seamless in practice area, and I would venture to say that most people who practice in South Florida would practice in all three counties.

Cosslett: Now you mentioned that at Holland & Knight there was more corporate fiduciary work than individual representation. What is the difference in those two areas? How does a corporate fiduciary litigation present itself?

Kelley: The largest difference is that it’s just not as personal. When you’re representing an individual that has a lot on the line, it’s a more personal experience for the litigant. That is not to say that corporate fiduciaries don’t have a lot on the line in these matters as well. A damage assessment is a serious matter, but it will generally have a more significant impact on an individual than on a corporation.

Representing corporate fiduciaries is also different in that personalities really don’t play into it. I came out of law school thinking, “If I have this set of facts on my side, I’m going to win this case.” That’s not the reality of it. The reality is that people play a large role in whether your client can ever make it to trial, whether they’re going to stand tough through the whole process, or whether they’re going to fold. Often the personalities of the litigants determine how your case is going to develop. That’s not as true when you’re doing corporate defense work.

Cosslett: A corporate fiduciary case would involve a bank as a fiduciary?

Kelley: Yes, a bank or any company with trust powers. A lot of the banks have trust powers. All the big banks do—such as Bank of America and Wells Fargo. And then a lot of the brokerage companies have trust companies such as Merrill Lynch and Morgan Stanley. And then there’s the private trust companies like Northern Trust, Brown Brothers Harriman, and those types.

Cosslett: So the essence of many of those claims would be breach of fiduciary duty by inappropriate investments in risky securities?

Kelley: You have to remember that right about 2004 we were in a market decline, so a lot of the work was involving allegations of improper investments. On a technical level, the issues are very interesting but it’s definitely a subspecialty. But there are often also construction actions in which people argue over document interpretation, saying that they aren’t getting enough distributions or that the trustee is giving too much money to one over another. There are always those types of issues.

Cosslett: In a personal context, do you ever get tired of people being greedy?

Kelley: People always say about divorce law, “Ah, divorce law. These people are terrible.” We see a lot of the same behavior in trust and estate litigation. But often these litigations aren’t really about the money. They are about family disputes that have always been there: “Mom always loved you more so I’m going to get you back now.” What often drives these litigations is pure, longstanding, personal spite. And people don’t act rationally when you’re trying to resolve these cases because it’s personal to them.

With a company, the analysis is more logical: “What’s the best financial outcome for this case? Is it better to settle it, or should we take a chance in litigation because the range of outcomes may be better for us?” With individuals, it can be totally illogical, irrational, and based on personal feelings. It’s akin to divorce litigation because there’s a pot of money out there, and everyone thinks they deserve it. Also, there’s an emotional overlay if somebody has passed away. If a litigant’s mother, father, sibling, or spouse has just died, it raises the stakes on an emotional level.

Cosslett: Do you find yourself being a mediator, a lawyer, and a therapist? I get a sense you’re a very calm person.

Kelley: I think I’d be a pretty bad therapist, but I to do try to be calm. You can’t let it get to you. You want to do the best job you can for your client, but if you get involved personally, you’re going to have a lot of stress in your life.

Cosslett: You’ve mentioned that your practice is divided into fiduciary litigation, estate planning, and estate administration. What’s involved in litigation? What’s involved in estate planning? What’s involved in administration?

Kelley: Fiduciary litigation tends to be the largest part of my practice because it’s so time-consuming. About sixty percent of my practice is in litigation. You have the pretrial work, depositions, discovery—those kinds of things. Then you have the phase leading up to trial, the trial, and mediation. It is very specialized and in many ways, different than other types of litigation because fiduciary litigation involves a distinct area of the law.

Cosslett: At trial , are you in front of a jury or are you in front of a judge?

Kelley: We’re rarely ever in front of a jury. All will and trust cases are equitable in nature, and you’re only entitled to a bench trial. A fiduciary is normally subject to equity, because if you look at the way that the fiduciary holds title to property, there’s a split between the equitable and the legal title. They don’t really own property in the sense that if you go buy something, you own it. They’re holding it for the benefit of others.

The concept goes all the way back to England, where you could not sue a trustee at law. You had to sue them in the ecclesiastical courts. And that has carried over into our law. And remember, our courts used to be divided into equity and law courts. Florida merged the two types of court into one, so our courts in Florida have both equity and law jurisdictions now, but there’s still a distinction between the two.

Cosslett: What is your trial strategy in a bench trial? Do you just present the facts, or do you attempt to add a little drama, a little flair?

Kelley: It really depends. You can’t answer that question until you know the judge you’re in front of. Some of them strictly follow precedent and others are more influenced by the equity side of the equation. And it’s always different. All judges are people, and they’re affected by different things.

Cosslett: So you take your strategy from the judge that you’re appearing in front of?

Kelley: Yes, and we are lucky here in Broward County. We have great judges in probate. They are appointed to the division and most of them stay there for the remainder of their career. Probate is a very desirable division in Broward County. We have three judges, and you get to know them because you’re in front of them all the time. So you know what the judge is looking for and you can determine what your trial strategy is going to be from that. Of course, it’s not as dramatic as being in front of a jury.

Cosslett: What is the jurisdiction of the probate court? What are all the areas that it encompasses?

Kelley: All probate matters. So anyone who passes away and has a will is involved in probate. Also, in Broward County it encompasses all trust matters, which includes trust litigation. That is pursuant to local order, so that’s not always the case. At the trial level, we have county and circuit courts and small claims courts. Small claims is minor matters. County court is matters up to a certain dollar amount, and then above that you’re in circuit court. All probate matters, trust matters, and guardianship matters are subject to the probate court jurisdiction. As we saw from Anna Nicole Smith, disposition of remains are also in probate court.

Cosslett: How much of your work is administration and what does administration involve?

Kelley: Probably twenty to twenty-five percent of my work is administration. When a person passes away, administration involves getting his or her property to the rightful beneficiaries. If it’s through a will, it involves getting it probated, getting creditor issues resolved, and getting the tax issues resolved. It is the same on the trust side, but you’re not subject to a probate proceeding. In trust administration, you’re unsupervised by a court, but it’s the same procedure as probate.

Cosslett: Now once you’re in probate, you’re under the watchful eye of the probate court, which ensures that the personal representative is doing what he needs to be doing and is not being a bad guy. Why do people say, “Avoid probate”?

Kelley: That idea was pushed a lot by people who wanted to either sell trusts or serve as trustees on trusts. In Florida, it’s not that bad to go through probate, and there’s actually some benefits to doing it. Right now, if you go through probate, you publish what’s called a notice to creditors, and you have a three-month period where creditors can file claims, and if they don’t, they’re barred.

If you don’t do a probate, creditors have up to four years to step forward. So a trustee could distribute all the property, have no idea about the creditors, not even check to see if there are any, and then the creditors come back after the distribution of all the property and say, “Hey, Mr. Trustee. Where’s my money? I’m going to sue you because you breached your duty to me because you didn’t make sure that I was taken care of.”

So there are some advantages to probate. And, as you said, it’s supervised. The court is going to make sure that people aren’t stealing money and that everything’s taken care of: the taxes are paid, the creditors are dealt with, and everything is done before they discharge that personal representative.

Now, it takes time to go through probate. It’s just like any other process. If you’re going to work with a government entity, it’s going to take time. They’re slow and they’re understaffed and they’re backlogged, but it’s not that onerous of a process in Florida. I think a lot of states have more onerous procedures that have resulted in people saying, “I don’t want to go through probate. I don’t want to pay these probate attorneys. I don’t want to deal with the judges.” And, if you have a close family that’s not fighting with each other and you have someone you trust who can administer the trust, that’s fine. You don’t need that oversight.

But I always say to people: “There’s probably not one individual non-corporate trustee—Uncle Tom, Uncle Joe, or whoever it is—who’s running the trust, that isn’t doing something wrong. It’s still a complicated procedure with an entire chapter under Florida law imposing duties and responsibilities and liabilities that these people are just incapable of fulfilling on their own. You still need a good attorney to bring you through the process properly.”

So there are a lot of things that aren’t being done in these trust administrations that should be done to protect both the fiduciary and the beneficiaries. If trusts are run properly, they’re beneficial. And one of the benefits of having a trust is that they’re private. If you look, for instance, at the estate of Michael Jackson, no one knows what his estate plan is because it was in a trust. Wills are filed with the courts. Any nosy neighbor can go down and look at the will. A trust is not filed with the court. It’s a private administration that’s not subject to court oversight unless someone invokes the court’s jurisdiction.

Cosslett: Not everyone has the assets of a Michael Jackson, unfortunately, but if you want to create a dispositive instrument in which person A won’t know what you’re giving to person B, C, and D, then the right implement is a trust rather than a will?

Kelley: That’s not the case in Florida because any beneficiary is entitled to a copy of the document. I’m talking about outsiders. Maybe you’re a high-profile person and you don’t want outsiders to know your business. Maybe there are other reasons you don’t want anyone to see it. Personally, I don’t care. If anyone wants to go look at my will after I die, let them go ahead. It doesn’t matter. But some people just don’t want that scrutiny.

The other benefit is that trusts are effective from the moment they’re executed. That’s why they are sometimes called “revocable living trusts ,” because they’re alive while you’re alive. If you become incapacitated for some reason, or can no longer manage your own assets, then the successor trustee can step in and take over for you. It’s a good guardianship avoidance tool because the other way is to go into court and get a court-appointed guardian and that becomes a matter of public record. It can be humiliating to the person who is incapacitated. You pull away all their rights. You can avoid that through a trust to a large extent be­cause the successor trustee can come in and pay all the bills and make sure the person’s taken care of.

Cosslett: It sounds like a good planning tool.

Kelley: It’s a good tool. A lot of people are saying, “I want a trust.” But, they don’t know why. They heard someone say in a seminar that they should have a trust. A lot of times you say, “Well, why do you want the trust? What’s the specific purpose?” And often people don’t need a trust. I always say to my clients, “I’ll do a trust for you. I charge you a lot more than a will. So if it’s worth it to you, then great. If not, you may want to reconsider.” So I don’t try to oversell trusts.

Cosslett: What are the downsides of a trust other than the fees?

Kelley: The lack of oversight. If it’s not a very cohesive family unit, there’s always the risk that someone is going to misappropriate those assets, and there’s no real way to tell until someone starts figuring out, “Hey, where’s all the money? How come I’m not getting a distribution?”

Now, you can always invoke the court’s jurisdiction to say, “Hey, Judge, something’s wrong here. I don’t think the trustee’s doing his job.” But that’s upon a request to the court. Otherwise, courts don’t interfere with the trust administration. People are people. They steal money. They do bad stuff. And with no supervision, it can be devastating, and that’s why you have corporate trustees out there. That’s a different situation. They’re going to do their job. They’re going to presumably administer the assets properly. You don’t have that same concern, but as I said, when it’s Uncle Joe, who doesn’t know how to manage assets, who may have a precarious financial situation himself, the temptation’s there to potentially misappropriate the money.

Cosslett: I don’t think I’m going to come to Florida. Between Uncle Joe stealing money and swindlers duping old people, it sounds pretty rough.

Kelley: But that’s why I have a job and that’s what I see. I’m called in when the kids come in later saying, “Hey, this person took $100,000 out of Mom’s account.” And I’m the one that’s hired to deal with that for the family, so yes, that’s what I’m exposed to a lot. Unfortunately, it’s ripe for the taking down here because of the elderly people. Their families are often not down here to supervise. They’re still up in New York or Pennsylvania, or wherever they came from. Often people come down as a couple, which is fine, and then one of them passes away and they’re alone. They’re looking for someone to rely on and sometimes, unfortunately, it’s the wrong kind of person.

Cosslett: We talked about litigation and administration. Is estate planning all about drafting wills?

Kelley: Wills, trusts, and tax planning. At the moment, it’s an unusual practice because we’re in a temporary tax situation that is going to expire at the end of the year if nothing happens. We went through 2010 for most of the year with no estate tax. We had George Steinbrenner die, no estate tax. Potentially a billion dollars in assets—and no tax. It was inconceivable.

When President Obama and the Congress finally reached a compromise, it was a two-year compromise. We don’t have any certainty and that makes tax planning very difficult. We don’t know. Right now we have a $5 million estate and gift tax exemption, but if the government doesn’t do anything, then beginning next year, it’s going to be reduced to a $1 million again. There are actually a lot of opportunities because of the present law. During your lifetime, you can give away $5 million without paying any tax. It is a very good opportunity for wealthy people to disperse their wealth to younger generations.

Cosslett: Of all the areas of practice that you have that you just described, which do you enjoy the most?

Kelley: That’s a tough question. I enjoy the litigation because it’s always challenging and there are so many different issues that come before you. We deal with tax issues, with construction issues, with challenging documents, with breach of duty. This area of the law is very technical and very complex, and most people don’t understand that. But I also enjoy the administration of trusts and estates. Unlike litigation, where it can take two or three years to reach a resolution, an administration will generally take a year from beginning to end, and there’s a sense of satisfaction that you derive from having gone from point A to point B.

Cosslett: Do you have an average day?

Kelley: I’d say probably no. I do a lot of work for the bar. My whole family does—my brother, my sister, and my father. My father wrote one of the best-­selling probate manuals in the state, and he donated the proceeds to the bar. He’s always been very involved in education and helping other probate lawyers, and we try to do that as well. There’s always something that needs to be taken care of, always an emergency. It’s never average, I can tell you that. It’s different than a straight transactional practice or a normal probate estate planning practice, where you meet with your estate planning clients and then do your administration. It’s not like that at all when you do litigation. So I combine it all, and it’s interesting.

Cosslett: You have been involved in some high-profile cases.

Kelley: The most recent case involved the remains of Anna Nicole Smith . When Anna Nicole died in Seminole Casino down here, there was a very high profile dispute over the disposition of her remains. It’s an area of law that is not established at all. There’s no procedure that you can use, and there’s no clear answer. After the Anna Nicole Smith trial, I was the co-chair on a committee that was formed by the RPPTL section of the Florida Bar to draft a statute to address the situation. There’s no good law. It’s conflicting. And it’s really just wide open as to what happens.

Cosslett: What is life like when you go from your daily practice, which is active and busy, but really a regional practice, to being in the national spotlight? What was your involvement with the Anna Nicole Smith case?

Kelley: That was my fifteen seconds of fame. I was sitting in my office one night, and I received a call from Judge Seidlin. The Judge was calling from his courtroom and said, “I’m appointing you as a guardian ad litem¹ in this case.” And I said, “Okay, Judge. It will be my pleasure.” And I added, “Well, if the other counsel wants to talk to me, here’s my number.” I gave my number out because I didn’t know that it was on live TV. I couldn’t answer my phone for three months. I can’t even remember how many calls I received. My voicemail was full after two days. Crazy people were calling me and saying, “You need to call me. I know the answer. I could tell you exactly what to do,” even though these people had never met Anna Nicole Smith. It was just bizarre.

And I remember around nine o’clock that night, I was still in the office, and I received a call from some guy claiming to be Howard K. Stern. I hung up the phone, and his lawyer called me back and said, “That was really him. He wants to talk to you about the case.” I talked to him for about an hour and a half. He had been appointed Anna Nicole Smith’s personal representative and executor on her will and was proposing to have her buried in the Bahamas. As part of my duties for the court, I actually ended up interviewing all of the parties concerned, including Anna Nicole’s mother. Being in that trial was a great experience, but it was very unusual.

Cosslett: At the end of the day, what was the decision?

Kelley: The decision was that she was to be buried in the Bahamas in the same plot as her son, who had died shortly before her. It was the right decision. It was funny because I had been slated that day to give my report to the court. And I’d handed out my report with the case law to all of the counsel, and I had all the case law assembled. I was ready to give my report when the father of the deceased son called. The Judge took his testimony via the telephone, and at the end of the conversation said, “All right, we’re done.” He walked out of the courtroom and I never gave my report. The decision was appealed and it was upheld.

I remember the Judge said to the reporters, “You can’t talk to the ad litem. He’s retained by the court. And you’re not allowed to talk to him. He’s not a party.” I wasn’t pushing an agenda like the parties were. And I remember walking out of the courtroom the first day and there were hundreds of reporters standing in line. And I walked around the corner, and they’re all ready, and they said, “Oh, it’s the ad litem. We can’t talk to him.” And they all turned around.

Cosslett: You also worked on a case involving the Winston family? That’s a famous name.

Kelley: It was Edna Winston’s estate. Harry Winston had died first, and then his wife, Edna, was the second to pass away. We represented Bankers Trust, who was a trustee on Edna Winston’s trust. The dispute was between the two sons over the assets and the estate and the Winston jewelry stores.

Cosslett: Are there other cases that you’ve had that are particularly interesting either by virtue of the names or by virtue of the issues or the personalities?

Kelley: I think a lot of my cases are interesting. We were involved in the litigation over the rights to some of Laura Ingalls Wilder’s books, The Little House on the Prairie. The main litigation was in Missouri where she passed away, but we had a part of the litigation in Florida. We were also involved in the Gus Boulis estate if you remember that one. He was gunned down in Fort Lauderdale under suspicious circumstances and there was extensive litigation in his estate.

Cosslett: It sounds like you have an interesting and diverse practice sprinkled with the occasional star name or particularly crazy cast of characters to keep you entertained.

Kelley: It’s a great area to practice in. Most people think, “Oh, trusts and estates is so boring.” But it’s exactly the opposite. It’s fascinating. I wouldn’t want to be in any other area of the law. I think it’s challenging intellectually and, on a day-to-day basis, some of the most interesting litigation.

Cosslett: What issues of professional responsibility are specific to a trusts and estates practice?

Kelley: I think the most important issue that we have to deal with is conflicts within families. You’ll often represent several members of a family—husband and wife, for instance. The classic conflict scenario is one where you prepare wills for both a husband and wife, and they leave everything to each other and their family members. The husband then comes in and says, “Oh, by the way, I want to leave everything to my girlfriend, but don’t tell my wife about it.”

Also, if you represent multiple generations of a family, disputes break out and you have conflicts. If there’s litigation, can you represent more than one beneficiary or do they have conflicts? Do they have diverging interests? Can you represent them as a fiduciary? Can you represent them in both capacities, as fiduciary and as beneficiary? Those are the kinds of issues that you have to be really careful about in trusts and estates. Potential conflicts of interest is the biggest issue that we face, and it’s constant.

Cosslett: How do you deal with the husband wanting to put his girlfriend in his will ?

Kelley: The bar advises that you deal with it beforehand. I always have a contract, which states, “This is a joint representation. Anything that you say to me will be disclosed to the other spouse, so there’s no confidence between the three of us. If you don’t want me to tell your spouse something, don’t tell me. And if you’re not comfortable with that, obtain your own representation.”

I have never had to deal with it, but, obviously, it comes up, and that’s why it’s the subject of ethics opinions. In real life, these things happen and you either take care of it ahead of time or you’re stuck with a problem and you’ve got to figure out how to handle it.

The litigation context can be more difficult. Sometimes people are aligned when you take on the representation, and their interests diverge when there’s litigation. Then you have to withdraw. Sometimes you can continue to represent one party if you can obtain a waiver. Sometimes you can’t. You always want to try to avoid a conflict. And to me, it’s generally not worth the time trying to salvage something if I’m going to be even close to a potential conflict. I just say, “No, sorry. I can’t do it.”

There is another conflicts issue that also comes up with some frequency. Next week in Fort Lauderdale and Tampa, I am heading up a seminar as chair of the Trust Law Committee and one of the issues involves gifts to lawyers in wills that they have drafted. You would think that lawyers don’t do that, but apparently it’s happening, and it’s happening frequently. People should be able to trust their lawyers and not have to worry whether he or she is angling to obtain a personal benefit.

And that leads to another issue that we face that actually hasn’t been squarely addressed: attorneys who name themselves in the fiduciary position, either as the executor or the trustee. And they’re entitled sometimes to significant compensation for that role.

Cosslett: You can understand why people would name their lawyer as fiduciary because they want someone who is able to deal with papers and who is very organized. Your attorney is a natural candidate to serve both of those roles.

Kelley: There’s a difference between someone making a considered determination to do that and a lawyer who coincidentally ends up in a lot of the documents as the fiduciary. There’s a big difference between a lawyer who says, “You should appoint me,” and lobbying for the position versus a client saying, “You know what? I’ve considered my options and you are the best choice.”

Lawyers need to discuss the options with their clients and say, “Have you considered a corporate fiduciary? Have you considered a family member or co-trustee?” And then after measured determination, they may say, “No, I think you’re my best option, and I understand that you’re going to be paid an additional fee. I understand that you’re going to hire your own law firm to represent you in your capacity as fiduciary and you’re going to be paid two fees.” So there’s a big difference between doing it when requested and when it’s in the client’s best interests, and somehow ending up on a majority of your clients’ estate planning documents as the fiduciary. You should always be working for your clients’ best interest and when a lawyer benefits personally it needs to be examined closely.

Cosslett: What advice would you give law students or practicing attorneys about going into trusts and estates?

Kelley: Fiduciary litigation is a great practice area, but it is hard to break into. There are not a lot of people who do it. While it’s a very good practice for a boutique firm, it is not always part of a big firm practice.

It’s also difficult to advise people to go into estate planning because we don’t know what the future holds in terms of the tax law. That’s a problem. If you want to get involved in the probate and trust area, students should try to take as many classes as possible. Students should also try to intern with trust and estate firms or in a big trust and estate office. And they should become involved with the trusts and estates section of their bar. I’ve been involved with the bar since the day I started because my father was. The more junior you are when you get involved, the better off you will be. You’re going to meet more people. You’re going to obtain more knowledge. It’s going to be beneficial to you. Trusts and estates is a great area to practice in.

Cosslett: There’s some talk in New York about a mandatory pro bono requirement for newly admitted lawyers. Do you think trusts and estate planning would be a good area for a pro bono practice contribution and a way for a lawyer to get his or her feet wet?

Kelley: There’s always the need for that: helping out low-income people with probate issues, durable powers of attorney, guardianships, and those kinds of things. Sure, there’s a lot of opportunity and there’s a lot of people that need it, so that would be great.

Cosslett: It sounds like Florida might need some good lawyers to come down and help to look after your senior population.

Kelley: Well, if you eliminated your estate tax up there, more seniors would stay in New York. I met someone the other day who said, “I wish I could live in New York, but I’m not going to pay that estate tax.” And you have to wonder how much money New York can bring in with its estate tax as compared to how much wealth would remain in New York if it was eliminated. It’s great that Florida benefits, but the amount of money that leaves New York because people don’t want to pay estate tax must be astronomical.

Cosslett: Someone needs to do a cost-benefit analysis, but that sounds like a subject for a different book.

¹ A guardian ad litem is someone appointed by the court to represent the interests of a person or entity that is unable to adequately represent their own interests in a proceeding, such as an infant, unborn or unknown person or entity.