Philip J. Halley could tell you about his practice; but then he wouldn’t be a trusts and estates lawyer

Published in 2009 Wisconsin Super Lawyers magazine

By Kevin Davis on November 16, 2009


He may not look like it, but Philip J. Halley, a trusts and estates attorney for Whyte Hirschboeck Dudek in Milwaukee, is trouble. From a journalistic perspective.

“I don’t talk about who my clients are,” he says politely. “My clients expect me to keep confidences. I’m not going to trade off of someone’s name. It’s different with other types of law and litigators, and with cases in court that are public.”

Well, what about his cases? “A lot of what we do doesn’t get into the newspapers,” he says. “We’re dealing with things that are very private.”

Thankfully, others are not as reticent talking about Halley.

“Phil is an absolute star, not only as a lawyer, but as a human being,” says Mark Miller, CEO of Whyte Hirschboeck. “He is a remarkable counselor to families and just a generous soul.”

“He is one of the best and brightest,” says Nathan Fishbach, also with Whyte Hirschboeck. “If there is any complicated issue, Phil is the lawyer of choice.”

“He’s widely recognized among trust and estate lawyers,” adds Kathleen Gray, a trusts and estates attorney with Quarles & Brady in Milwaukee. “It’s a highly technical specialty. It’s not about the art of litigation. You’re not a performer. It’s more about understanding the tax code.”

Which suits Halley just fine. “One of the great things about trust and estate law is that it really allows you to combine the analytical side and the personal side,” Halley says. “You really have to be a people person. You need to have people skills.”

Halley, who’s a shareholder in his firm and head of its trusts and estates practice group, works hard to make his clients feel comfortable revealing very private matters. Many probably shudder to think their personal business would become public, much less newspaper fodder.

“I can’t tell you how many times someone might say, ‘I’m embarrassed to say this, but …’ and they’ll tell you something very revealing about their family,” Halley says. “Everybody’s got something going on. You’re very privy to a lot of confidential information.”

In fact, in more than two decades, just one of Halley’s cases made the papers. It involved a dispute over the estate of a woman who committed suicide. Yet he’s still reluctant to discuss the case in any detail. “It’s common in this area of practice not to talk about these things. My clients aren’t looking to get any publicity.”

Not many go to law school with the intention of specializing in trusts and estates, and Halley didn’t either. Circumstances led him there. Disability led him there. After graduating from Ohio State, Halley came to Milwaukee in 1981 to clerk for a federal judge, thinking he’d get a couple years’ experience then move on.

“Afterward, I thought about going back to Ohio and interviewing with some firms in Cleveland,” he says. “But it just seemed like Milwaukee was a nice place to practice law.”

Looking out at a shimmering blue Lake Michigan from the 17th-floor terrace at his downtown office building on a recent summer morning, Halley admires the view. “Isn’t it something?” he says. “This is really a beautiful city.”


He grew up in Huron, Ohio, a town of 7,400 that is 50 miles west of Cleveland on Lake Erie. He’s the son of educators. Initially he attended Ashland University as a pre-med chemistry major, but changed his mind after spending a summer working as a hospital orderly. Transferring to Ohio State, he earned an undergraduate degree in economics in 1978, then a law degree in 1981, but was still unsure what he wanted to do.

With an interest in civil procedure and federal courts, he clerked for U.S. District Judge Robert W. Warren of the Eastern District of Wisconsin. “My wife and I wanted to try someplace different,” he says. “We didn’t have kids and thought we could live anywhere for a couple of years.”

Fishbach, then an assistant U.S. attorney who worked in the same building as Halley, remembers him well. “We tried cases before Judge Warren all the time. Phil was his law clerk and I know he worked long hours,” says Fishbach. “Judge Warren simply loved him, and spoke highly of him all the time.”

Then came a surprise. Two surprises, really. Not long after moving, his wife, Ellen, now an elementary teacher at St. Robert in Shorewood, got pregnant. The second surprise came when his wife had an emergency C-section and learned she would bear twins. Meghan and Beth were born in 1982.

“I think we were the last couple in America to have surprise twins,” says Halley, whose wife never got an ultrasound. “We didn’t know until the second one came out. I’ll never forget that night, walking down the hall and saying, ‘Yes!’” Even today, talking about that experience makes Halley misty-eyed.

When Halley’s two-year clerkship ended, and after he and his wife decided on Milwaukee, Halley, in 1983, joined Whyte Hirschboeck Dudek. It was then that he chose trusts and estates.

Part of the reason was his deteriorating vision. Halley first realized something was wrong with his sight when he was about 11. “Back then they didn’t have CAT scans and MRIs. The initial thought was a tumor. I remember we’d be in the car on vacation and everyone would look out and say, ‘There’s the Mackinac Bridge!’ and I’d say, ‘Where’s the Mackinac Bridge?’”

It wasn’t until he was in his 20s that Halley was officially diagnosed with optic neuropathy, a condition that makes it hard for him to read standard-size documents and books, as well as focus on objects at a distance. It eventually forced him to stop driving a car 20 years ago.

Trusts and estates, he figured, wouldn’t require him to travel much. He could work comfortably in his office, where he uses magnifying glasses to read and works from a large computer monitor.

In fact, other than the large screen and magnifying glasses, it’s not apparent that Halley has a vision problem. He certainly doesn’t make a big deal about it. “I drew the cards I drew,” he says.


At Whyte Hirschboeck, he gained expertise in marital property law—succeeding one of his partners as the co-author, with five others, on a revised edition of Wisconsin’s three-volume set on the subject in 1994, and periodically updating it since. He also taught marital property law for several years at Marquette University Law School, but eventually gave it up to focus on his practice and his family.

An important part of his practice is helping clients provide for their heirs while reducing or eliminating their tax burdens. “At a certain level, there’s planning that people need to do so they don’t leave a mess,” he says. “A lot of our planning basically has to do with property. I try to get things in shape for those left behind.

“One couple,” he adds, “struggled to decide how they are treating their children differently with their estate. There’s a lot of angst in that.” Some parents even have concerns about leaving their children too much. Halley likes what Warren Buffett says on the matter—Leave the children enough so they feel they could do anything, but not so much that they feel they could do nothing—but he doesn’t rush to volunteer such thoughts to clients. “I tend to listen more than I talk,” he says.

Halley also works with clients on advance medical directives—documents that spell out how doctors and hospitals handle terminal illness and medical matters—and helps direct gifts to nonprofits and charitable organizations.

Halley spends little time in court, and when he does it’s often on procedural matters. But in 1995 he argued before not just any court. “One of the greatest things I got to do was argue a case before the Wisconsin Supreme Court,” he says. “Not many trusts and estates lawyers get to do that. I just thought that was the coolest thing.”

Firstar Trust Co. v. First National Bank of Kenosha addressed the allocation of the burden of estate taxes, and Halley, whose firm represented Firstar, did everything he could to prepare. He tracked down cassette tapes of famous oral arguments, listening to how the pros did it, noting their styles and techniques. Once he began his oral argument, however, he learned quickly that there was little time for monologue. “You get a minute into the argument and the judges start asking all these questions,” he says. “That’s when it becomes not so much an argument, but a conversation.”

The court ruled in Halley’s favor on one issue and against on another. “But for me, it was really a neat experience,” he says. “For most people, it’s not that interesting.”

“He has a self-deprecating sense of humor,” Kathleen Gray says. “He’s a good person and a straight shooter.”

It helps that he works in a specialty in which most colleagues and competitors are not at each other’s throats. “My practice area is very collegial,” he says.

In fact, he and his colleagues, including Gray, have a regular study group. “Trusts and estates lawyers, we are all studious types,” she says. “We’ve been out of law school 30 years, but we still need to study up.”


Since he doesn’t drive, Halley usually walks or buses to work from his Milwaukee home. Sometimes he bikes or takes a cab, and, in the latter case, he’s befriended a Somali cab driver who has shared his life and experience as a Muslim. “He is my connection to the Muslim world. I was riding with him on the day after 9/11. We talked a lot about what he believes in. It’s been a real experience for me, especially after all the negative things that have been said about Muslims. I wouldn’t have that in my life if I didn’t have this vision problem.”

Reading is difficult, but every year Halley listens to about 20-25 books on his iPod. He’s a big fan of Tracy Kidder and frequently gives away copies of Mountains Beyond Mountains to friends. The book chronicles the story of Dr. Paul Farmer, who opened a medical clinic in Haiti that grew into an international medical relief organization. “He’s my hero. I have given away so many copies of this book just because it is so inspiring. It’s about the power of the individual,” Halley says. “It’s an example of how one person’s vision for change can make a difference if they’re really committed.”

Halley tries to make a difference as well. He has served on a number of boards, including Dominican High School and the Wisconsin Eye Research Institute. He’s also done a lot of pro bono work throughout his career, including assisting with Whyte Hirschboeck Dudek’s Pro Bono Guardianship Clinic at Children’s Hospital of Wisconsin.

He and his wife are most proud of their three daughters. The twins took the medical route he abandoned: Meghan is in East Africa studying medical anthropology, while Beth is in medical school at Ohio State. Their third daughter, Laura, is a high school social worker in the Bronx. “My daughters are much more interesting than I am,” he says.

Given this attitude, it’s hardly surprising that Halley wondered why this magazine wanted to profile him in the first place—even though he’s been ranked among the top 10 attorneys in Wisconsin for the last three years. “If you’re going to be in Super Lawyers, you need to talk about the people you work with,” he says. “I’m just trying to be one of the top 10 lawyers on the 17th floor.”

As we said: Trouble.

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