Benjamin Lee Cregger

What made you want to go to law school?

I was inspired by the work of the Low-Income Taxpayer Clinic, a coworker being treated very poorly by a former employer, and a sticky situation I had while working as an accountant when I was asked to commit, but didn’t commit, what I felt (and now know) was unlawful tax evasion. I wanted a career and a purpose that I was proud of and never felt like I needed to make an ethical compromise to succeed in. Law school offers a lot of great tools that can be used for a wide range of purposes. I am very grateful to have had the privilege to be a part of Lewis & Clark’s program.

Why did you choose Lewis & Clark?

I originally picked a few places to apply for that had offered good law review and clinic options, classes on my initial interest of tax law, and ideally had a strong commitment to the community and the environment. I went to the admitted student’s day for another JD program, and it just didn’t feel like the right fit. It is absolutely worth it to go to the admitted student’s day, if you can, because there is so much that a website can’t convey, and it is a major decision. I was also waitlisted for my original top pick, leaving me with only about a month to organize a move right before the start of school, after I was accepted there late, and that seemed logistically challenging to also juggle while also helping organize a funeral ceremony during that same timeframe. I was honestly a little unsure until my first day of classes, during Summer Institute, but then I immediately realized that Lewis & Clark was the perfect choice for me, and I have not looked back since. It ended up being everything I wanted. My advice: Apply for several programs and see what ends up being right for you. It might end up being a little different than what is initially expected.

What have you been doing since graduation?

Around graduation I originally had an offer that I intended to accept, to be the director of a Low-Income Taxpayer Clinic, providing low cost or no cost legal services for those unable to otherwise access critical legal aid services, however it was withdrawn when I fell a few points shy on the bar exam. Fortunately, I was also offered a judicial clerkship shortly after receiving the bad news. I am grateful that I had the opportunity to work at the courthouses and I think it is a fantastic opportunity for anyone to consider after law school. Ideally, you won’t stumble on getting licensed like I have, but if you do—and an unfortunate consequence of the current system is that some always do—there are still plenty of fantastic options and experiences available. Being a clerk was sort of like my 4L and 5L, as I feel like I learned so much. Particularly for anyone interested in or curious about litigation and courtroom advocacy, civil or criminal, should really consider a clerkship. There is so much there to see, what works and what doesn’t, from a much different perspective than class can provide. School is just the first step on what is hopefully a lifelong journey of learning.

How did Lewis & Clark prepare you for your career?

It did not seem like it at the time, but during my first year I had a professor who appeared to be really hard on me and was pretty straightforward about several criticisms regarding my writing. I was putting in so much work, dedication, and passion—really trying to improve my writing to be the best possible future advocate I could be but didn’t seem to achieve any of the positive results I desired. We come from two radically different backgrounds and have wildly different ideas about what the purpose of law, and communications, in society should be. And that, oddly enough, is a really great thing! During litigation, one side is probably going to lose, or make some sort of compromise. A judge is not always convinced of every lawyer’s best available argument. Even a lawyer’s client might not always agree with what would otherwise be great work. Bad results happen to people who try their best. As best I can tell, bad results eventually happen to everyone, and it is essential to know how to recover and adapt. For me, Lewis & Clark’s program was a challenge but that is what I wanted and what I think law school should be. And one of the most valuable skills is being able to work with someone adversarial that you fundamentally do not agree with in a way that is hopefully collegial and productive. While it was a disappointment at the time, being able to take a few early falls in the safety of school was incredible preparation for what followed. What matters is trying again and not giving up hope for the better world, the just and fair world, that you dream of.

What would you say is the most important thing you learned at Lewis & Clark?

It was during the pandemic, and someone very dear to me was terminally ill. I was so focused on school, trying to build a career, that nearly all of my attention was there instead. And I know that is what they wanted for me to do because that is how you love and care for someone. But my biggest regret was not hitting pause, to take a little longer to get there, and be in the place I should have been. It is all to easy to get caught up in school, work, and the causes we are passionate about. But the most important cause, the most important work, is to also take care of yourself. If I could do it all over again, I would have taken time off school to take care of something more urgent and graduate a year later. I am sure the school would have worked with me to let me focus on a dying family member, but I foolishly never asked.

List up to three activities that you were involved in at L&C. Pick the ones that are most important to you and tell us why.

NEDC was an amazing opportunity to get involved. Animal Law Review was, for me, the most educational. And the chance to be included at the Low-Income Taxpayer Clinic was incredibly inspiring.

Tell us about a meaningful Lewis & Clark academic experience that happened outside of the classroom.

At least back during my 1L, we had these amazing presentations during lunch. The free lunch, as a broke student, was great but really it was just an incredible opportunity to explore and learn more about a wide range of legal topics. I tried, and failed, to go to them all… maybe not the best strategy but I loved it. I learned a lot of stuff, not on the syllabus, and still passed my graded classes. It is a really special opportunity, to just focus on learning and absorbing as much as you can, from as many sources as you can. If someone offers you a free CLE, even if you do not need the credit, it is always worth trying to make it.

Do you have any advice for students making their final law school choices?

You have to be the one passionate and excited about whatever it is. What works great for one person might not for another. But also, nothing is perfect. So there needs to be some compromise as well. I wouldn’t compromise on anything essential, however. A school picks who it offers acceptance letters to but that is really just half of the picture. The program also needs to fit with what your goals, aspirations, and desires are. Like a good job interview, it is about what vision both sides have for the other and if those things are mutually in alignment or not. It was the most important choice in my life and I am grateful to have had the privilege not to feel rushed or forced into anything. I think a lot of people are very unhappy, in school and afterwards, because they did not take the time to genuinely consider what was right for them while also being realistic about what is worth compromising on and what is not. I think a gram of prevention is worth a kilo of cure, in that regard: If you can, strategize now the best that you are able. Things will change, expect the unexpected, but having a ballpark estimate of what it is that you want, what is realistic, and what you can compromise on is incredibly valuable. Adjustments are going to happen but this is an important step in your life and worth spending some time to sit with.

What was the hardest thing about adjusting to law school?

When I was a judicial clerk during criminal proceedings, I often found myself resonating and having the most in common with many of the defendants. My life, before law school, was much different than many others who take that journey and I feel, without the kindness and guidance of others, my life would have instead taken a destructive path. In my personal life, I share precious little in common with what I perceive to be the common ground among lawyers and law students. My values, and my beliefs, are often in tension with others. It is difficult, I suspect for a lot of people, to build lasting connections. In the best of times, additional perspectives can be invaluable. But there is a personal cost as well, to never feel quite like you fit in or do not entirely belong where you would like to be. I think the legal profession is in dire need of broader, and more diverse, backgrounds and experiences as well as a culture of tolerance and inclusivity. In the future, hopefully we can do more to help cultivate that further and ease the burden of being different because those differences add a tremendous net value.

Who was your mentor on campus? Why did you consider this person your mentor?

JB was the first lawyer who spoke to me like a colleague and equal and showed, by example, how to help make this world a better place. I am so grateful, and fortunate, that I met her so early in my law school journey.

What was your favorite spot on campus?

The best spot on campus is, of course, the library during a fall day, when the leaves are changing color and it is just a little too cold or damp to be outside for very long. There are these towering windows that look out on the state park that is a part of the campus. It is the best part of the whole trail. How many stressful tests has that majestic tree stood through? Surely, we can also stand another. That bird, that squirrel, even that slug have all found some ingenious way, not just to survive, but thrive in the face of adversity. That library is just another part of the forest that happens to have books, instead of mushrooms, in it. I hope that we will protect all of it, forever, to safeguard what we have borrowed from the future.

What is your favorite thing about living in Portland?

The most important thing about a city is a robust public transportation system and a commitment to taking care of everyone in the community. Portland is far from perfect in those, and other, regards but it makes a substantial effort to be. It is a fantastic place to call home.