Many Californians, even those passionate about chess, may not be familiar with the name of Patrick Wolff. Grandmaster Wolff has been a significant figure in the California chess community for decades. As a two-time U.S. Chess Champion and a respected author and coach, Wolff has made substantial contributions to the chess world, both through his competitive achievements and his efforts in promoting the game. For California’s chess enthusiasts, discovering Wolff’s work could provide valuable lessons and inspiration, enriching their understanding of the game and its rich history. For California voters, learning about such an esteemed candidate is essential for choosing the best person to be our next Insurance Commissioner.
Please enjoy my interview with GM Patrick Wolff.
Who introduced you to chess?
My father, when I was 5 years old.
Where was your first scholastic chess tournament? How did you do?
Western Massachusetts scholastic (K-3) regional qualifier. I came second, at the age of 9. The next year, I was Massachusetts state scholastic champion, 4-6 grades.
Who was your chess hero growing up?
Bobby Fischer, because I loved My 60 Memorable Games. It was very sad to learn later his manifest flaws as a person.
Winning the 1983 National High School Championship and the 1987 U.S. Junior Championship was quite an achievement. Who were your coaches during this period?
John Curdo, and then Edmar Mednis.
Who did you consider to be your biggest rivals at that time in your life?
Alexei Dreev was my nemesis after he beat me and came first in the World Cadet Championship in 1983. In the US, my biggest rivals as a junior were Stuart Rachels, Alex Fishbein, Max Dlugy, Joel Benjamin.
Do you feel that chess had an impact on your college admissions process?
Yes, I’m quite sure it helped me get into Yale out of high school, and then into Harvard later on as a transfer student.
How did you manage to balance college life with your chess career?
Badly! 😂 I dropped out of Yale after Sophomore year to play professionally. Then when I eventually transferred to Harvard after several years, I took a semester off to be Anand’s second in the 1995 World Championship, to write a book about that match, and to win the US Championship. But I eventually graduated and started my career outside of chess.
Tell me about the the Wolff Cup?
My friend Chris Chabris started it, as an annual commemorative match between Harvard and Yale since I went to both schools.
On your road to becoming a Grandmaster, you obviously traveled a lot. What was your favorite tournament location?
There are too many to name just one!
You won the U.S. Championship in 1992 and again in 1995. Could you please take a moment to describe your recollection of these tremendous accomplishments to the current generation of California chess players.
When I won in 1992, it was a watershed moment that took me to a new level, which was made possible by working for several months as Anand’s second in his match against Ivanchuk. When I won in 1995, it was a wonderful capstone to my career, as I was already at Harvard and planning soon to move on — and that victory was made possible by working as a second in Anand’s World Championship match against Kasparov.
How has chess connected you to other people, especially those in business and finance?
Chess has always been a way to meet people, and many people who learn about my chess experiences find it fascinating. It’s a good calling card!
What lessons has chess taught you that you applied to your business ventures?
Getting very good at chess taught me how to learn anything if I apply myself, and it taught me to think strategically and to persevere.
How did you become so knowledgeable on how insurance companies operate in California?
I spent four years building an insurance brokerage business from 2001-2005 at a major bank, and then 20 years after that as a financial analyst, so I started from a strong knowledge base. Then I took most of 2025 to apply myself to learn insurance regulation in California. I’m good at learning.
Can you use chess as an analogy to describe the current insurance crisis in California?
The current regulation has been managed like a chess player who does not understand the core principles of development, pawn structure, king safety, material, initiative, etc. To someone who does not know basic strategy, the game looks impossible. But to someone who does understand, it all makes sense and is perfectly solvable.
Whether on the chessboard or in the business world, you are known as a great planner. What is your plan to fix California’s insurance market?
We have to hold insurance companies accountable, increase choice and competition, and improve transparency. I published an op ed that explains it at https://calmatters.org/commentary/2026/01/insurers-california-competition-wildfires/. And you can read more on my website at https://patrickwolff.com/my-plan.
Thank you for your time. How can readers find out more about your platform and help out your campaign?
Go to https://patrickwolff.com/ to learn about my campaign and contribute online at https://secure.ngpvan.com/XdzwfjNj5ky0W00y8sLrjQ2.