Profile: Philip Pillsbury

Out of order is how this insurance-bad-faith lawyer approaches trials

Stephen Ellison
2020 September

Tradition and principles carry a lot of weight in the courtroom, but that doesn’t mean a lawyer has to approach every trial conventionally. Just ask Philip L. Pillsbury Jr., founding partner with Pillsbury & Coleman LLP, whose formula for trials might catch people off-guard.

“We bring a lot of young lawyers in, and … one of the things I do when the young lawyers come in is I tell them we try every case here backwards,” Pillsbury explained. “That always catches them by surprise. We decide this early on. When we’re sitting around brainstorming the case, this is when we start to try the case backwards.”

Here’s how it works, according to Pillsbury: The first thing he and his team do is ask what, precisely, is the jury going to be asked to do. What decision are they going to be asked to make? Then he asks: What are the jury instructions and why will the judge instruct the jury in this way?

That’s followed by asking: What are your causes of action, and what is the evidence being put in front of the court? Once all that is determined, Pillsbury’s team is back to how they’re going to frame the complaint, how they’re going to frame the issues, and most important, what their themes are for the case, he explained. Finally, they figure out how the evidence plays into those themes.

“If you’ve really done it backwards, you’ll have a vision of the case and how it’s going to work,” he said. “I find some people make the mistake and say, ‘Well we’ll figure all that out later, let’s get discovery going. Let’s get the complaint going, maybe we can settle the case.’ I never think of a case that way. Every case that comes to our office is a trial case. … That’s how we do it.”

He’s no stranger to record verdicts

Indeed, that’s how it’s done, and the results show it’s been done well. Pillsbury has obtained a number of multimillion-dollar verdicts and settlements over the years including a $26.5 million verdict in 1998 in Vann v. The Travelers, which called for $25 million in punitive damages, one of the largest such awards in the country to be affirmed on appeal.

Among many other significant wins, Pillsbury in 2008 also secured more than $400 million in insurance proceeds for a national manufacturer facing more than 50,000 asbestos lawsuits.

But it hasn’t always been about what he can accomplish in monetary awards. Over time, Pillsbury discovered he could use his court skills and legal savvy to make a difference in other areas. And after one particular case, in which he and a paralegal triumphed over a whole team of lawyers across the aisle, he decided to apply what he learned by helping an organization that was a critical service to the community.

Pillsbury became the chairman of St. Luke’s Hospital in San Francisco, where eighty percent of the client base was Medicare or Medi-Cal. The hospital easily could have gone under, but for Pillsbury’s actions. The Sutter Health system had been essentially poaching St. Luke’s doctors in a way that he believed violated antitrust laws. So, he called on two lawyer friends and brought an antitrust action against Sutter.

“We eventually resolved that case – at the end, we settled,” Pillsbury said. “Sutter agreed to pay a substantial amount of money to rebuild practices at St. Luke’s, and we also received $10 million to put back into community health services. Fast forward to today, and St. Luke’s has been rebuilt. It’s a brand-new hospital, they call it Mission Bernal. It was something not just anyone could do – you have to have a sense of what justice is and who your audience is, and you have to have the ability to pick really good lawyers. We were able to put that together. It was something that was a big part of my life.

“What I learned how to do and had the luck to do was spread my life out in different areas – the environment, education, health – not only through litigation, but also by using the ability to articulate a point of view and articulate what is just,” Pillsbury continued. “A jury wants to do justice, and they understand what justice is. So, my job in a plain way is to show them that my client has a just cause.”

Treading his own path quickly

Born and raised in San Francisco, Pillsbury came from a family of doctors. He chose law because his sister “sort of badgered” him into it, telling him more than once he should be a lawyer. Once he thought about it seriously, it actually made sense, he said, as there were things a person could do in law that he or she really couldn’t do in other ways of life.

So, after he graduated from Middlebury College in Vermont, Pillsbury went to law school at what was then Northwestern College and is now called Lewis and Clark College in Portland, Oregon. He chose the school for its preeminence in environmental law and in trial work, as he had designs on becoming an environmental trial lawyer. But, of course, it didn’t work out that way, and he started his career at a litigation firm in San Mateo that didn’t do any environmental practice.

“They represented insurance companies, so it was the furthest thing from an environmental law firm as you could get,” Pillsbury recalled.

As it turned out, Pillsbury was there for only a year. The principal litigating partner told Pillsbury he was leaving and starting his own firm and asked if Pillsbury was interested in coming along. So, a year into his law career, Pillsbury became a name partner in a firm representing mostly insurance companies on home office cases, he said. He learned a lot about insurance, about how home-office cases work and about how carriers work – how they evaluate cases. It was another test as to whether or not it was what he wanted to be doing with his life.

Pillsbury eventually moved up into San Francisco, heading the branch office of the firm, and got a call one day asking him to go back to San Mateo and anchor the firm from there. He declined the offer and decided to stay in San Francisco.

“I hung out a shingle, and began to work on the plaintiff side,” he said. “I had some terrific cases and clients. There were lean times for a couple of years – I had a young family, a young son, ultimately ended up with four children. It’s hard to have your own practice when you’re doing that, but I was lucky enough to have some good luck.”

Persuasive triumph

Before he went all in on the plaintiffs’ bar, Pillsbury had a memorable trial against a formidable foe in Contra Costa County. He went up against the legendary e. robert wallach  (a/k/a “lower case bob”) in a medical malpractice case in which he was defending an accused doctor whose patient had an undiagnosed brain tumor. Wallach was a Hall of Fame trial lawyer, and Pillsbury was reminded of that fact all too often during the trial.

“I remember going up there every day for that trial,” Pillsbury recalled, “and every day someone would ask me, ‘You got a trial?’ And I would say, ‘Yes.’ And they would ask against who. And when I told them it was bob wallach, they would move away from me as if I had a disease. They didn’t want to catch bob wallach from me.

“He is such a fabulous lawyer that he put this case together in front of the jury, brick by brick, piece by piece, and it was seamless,” Pillsbury continued. “But we had some good fortune. We developed some doubling theories and were able to show the jury that when the patient had last visited the doctor, the tumor wouldn’t have been visible by the doctor or even by an MRI because (an MRI) could only see one cubic centimeter. We were able to work back in time, using slides to demonstrate that, at the time, an MRI could not see anything less than one cubic centimeter.”

Pillsbury told an old story as an analogy to persuade the jury about the biological doubling theory for cells: The doubling theory starts with a cell or two cells, and then as each cell continues to double, the mass grows exponentially and enables one to calculate when the mass will get to a certain size.

In his opening statement, Pillsbury talked about the tale of the Pasha of Persia, who was delighted with a game that came to him called chess, Pillsbury explained. The Pasha wanted to know where the game originated and was told it was from a small village in a tiny corner of Persia. The Pasha insisted the man come forward and offered the man his weight in gold. But the man was humble and asked only that the Pasha get a chess board and place a grain of wheat on the first square, two on the second, four on the third and so on until the board was full.

“By the time you move all the way around the board, 64 squares, that 64th square would represent more wheat than was grown in the entire world last year,” Pillsbury said. “So, I explained that to the jury, and it caught their attention. I said, ‘We have a very small tumor, and this is how fast it doubled, but it never got to the point where it was one cubic centimeter. That became the theme of the case, and fortunately, the jury saw it our way.”

During the trial, Pillsbury got to know Wallach very well and admired his skills and demeanor. He thought if he could be a plaintiffs’ lawyer like Wallach, it would be something worthwhile, and he eventually moved in that direction, he said.

“He had the ability to let the jury know his client was the most important person in the world for him, and he was able to try this case against anyone,” Pillsbury said of Wallach. “Turns out he didn’t have the facts.”

Family and the environment

When he’s not working, Pillsbury spends time with his grandchildren and supports his children both emotionally and economically, something that’s very important to him, he said. He also spends a lot of time with the Yosemite Conservancy, for which he served as chairman for a number of years and continues to serve on the board.

“We just completed the Mariposa Grove, we’re now completing Bridalveil Falls, Lower Yosemite Falls, working on housing for the park, working on making it a better experience,” he said. “That takes a lot of time. It’s a wonderful organization, and I enjoy that.”

He’s also a chancellor for his church, enjoys playing golf a couple of times a week and cycling. “I stay pretty busy,” he admitted.

On the subject of passing along advice to young lawyers, Pillsbury said he’s in a position to do so often. Here’s what he usually tells them:

“One, in our office, the enemy is not inside – the enemy is out there,” he said. “By that, I mean opposing counsel, people who are trying to stop what you’re trying to do with your client. Two, don’t take yourself too seriously, but be serious about your work. Understand that working with your client is the most important privilege that we have.

“And if you are a trustworthy lawyer, you’ll make good friends on the opposite side, and you’ll be able to do wonderful things for clients. Not always, but that’s the goal.”


Getaway spot: Windy Gap, above Golden Trout Camp in the Eastern Sierra

Go-to Music: Bob Dylan, Visions of Johanna; Grateful Dead, Box of Rain; Puccini, Turandot

Recommended reading: Atul Gawande: “Being Mortal”; Hilary Mantel: “The Mirror & the Light”; Scott Turow: “The Last Trial”

Dream Job: The one I have

Words to Live By: “Now the ears of my ears awake, and now the eyes of my eyes are opened.” – e.e.cummings

Stephen Ellison

Stephen Ellison is a freelance writer based in San Jose. Contact him at

Profile: Philip Pillsbury

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