Blue Ocean Global Technology Interviews William (Bill) Choslovsky | Partner at Ginsberg Jacobs LLC

Bill Choslovsky is a seasoned litigator and restructuring attorney with over 25 years of experience, known for his practical, solution-oriented approach. A Harvard Law graduate and former clerk to both state and federal judges, Bill combines legal acumen with a strong financial foundation. He has litigated major class actions and counseled diverse clients through complex bankruptcies and workouts. Bill is deeply committed to pro bono service, earning the U.S. District Court’s highest honor for his advocacy in civil rights litigation. Beyond the courtroom, he serves his community through nonprofit and civic engagement, and still finds time to coach youth baseball and write passionately.

Tell us about your professional life. Why did you choose to work in the legal industry?

Contrary to the typical path of following in one’s father’s footsteps—my father was a doctor—he astutely recognized that a career in medicine might not align with my skill set.

My fascination with the power of the written word and oratory skills began to take shape during a high school course called The Supreme Court. We delved into recent US Supreme Court opinions, engaging in arguments on both sides. What stood out for me was not the partisanship of choosing a side, but rather the art of crafting compelling arguments and the challenge of persuasion.

In college, I took a speech communication course to sidestep a writing requirement. Surprisingly, it turned out to be a pivotal experience. Reading about speech communication theory, I discovered the concept of inoculation—presenting opposing arguments with a small piece of their merit. This idea, akin to a vaccine introducing a trace of the virus, fascinated me and has stayed with me throughout my career. The study of speech communication and its application in the legal field became a compelling aspect of my journey.

As the years have passed, my attraction to the legal profession has evolved. Whether it’s presenting in court or crafting persuasive briefs, the challenge of making a compelling case remains a driving force. While my colleagues in real estate law seek harmonious transactions where everyone can be a winner, I find the dynamic nature of litigation more appealing. In this area, there are winners and losers, and—even in defeat—there’s a sense of fulfillment from being in the midst of the action.

What does your typical day look like?

My typical day has undergone significant changes since the onset of the pandemic, reshaping my routine and work dynamics. Previously, I would frequently commute to federal or state court, a practice spanning three out of five days each week. These visits primarily involved routine motions and scheduling matters rather than high-stakes trials or impactful motions, such as those determining the exclusion of an expert. Even today, routine matters continue to dominate approximately 90 percent of my time.

A positive outcome of the pandemic-induced adjustments is the increased efficiency and cost-effectiveness. Thanks to virtual court proceedings via Zoom, my commute time has significantly decreased. Now, I find myself attending court virtually three days a week, mainly during the morning hours for routine matters.

Ideally, I allocate weekends or late nights, when the office is quiet and phones are silent, for my true passion: writing. I enjoy the process of writing and—perhaps with a touch of self-assurance—I believe my unique touch adds significant value.

So, a typical day involves reviewing work from associates (particularly in discovery, where document requests and interrogatories are assembled). Despite having associates, one area where I may fall short is delegation, especially when it comes to depositions and critical tasks like responding to a motion to exclude someone. My day is predominantly consumed by hands-on tasks rather than client pursuit, a choice I make despite my career stage. While transitioning to a more client-focused role might be advisable, I take pride in being a hands-on lawyer.

What is one trend in your industry that excites you?

When it comes to legal industry trends, there are some aspects I’m not too fond of, such as the increasing reliance on AI and outsourcing, making legal work more standardized and less reliant on lawyers’ thinking. Also, the shift to hybrid work arrangements, where associates and people have less in-person interaction, is something I find disheartening. I believe there’s value in human beings physically being together and having spontaneous conversations. The reactions that happen when people interact in person are invaluable, and I think we’re losing some of that.

However, a trend that excites me, particularly in terms of technology, is the ability to handle cases virtually. This shift, accelerated by the pandemic, allows me to appear in cases around the country that I might not have taken before. Virtual proceedings have made geographical barriers less relevant, enabling me to lead a case in Alaska, for example. This trend has expanded opportunities for legal professionals and, in some ways, made the legal system more accessible.

Regarding AI, while I have reservations about its impact on routine tasks and non-litigation work, I see its potential benefits, especially in transactional matters like drafting contracts. The efficiency and accuracy demonstrated in AI experiments for drafting legal provisions, as I witnessed in a recent seminar, were quite impressive. For routine tasks in the transaction world, such as corporate documents or real estate contracts, AI can be a valuable tool.

However, I believe that litigation, my specific area of practice, will be less affected and will adopt AI later compared to transactional areas. Writing a persuasive brief involves a level of creativity and strategic thinking that may not be easily replicated by AI. While AI may have an impact, I believe it will be less pronounced in the realm of litigation than in transactional work.

How have you differentiated yourself, and what underpins your success?

When clients hire me, they know it’s about an 80 percent positive experience and 20 percent potentially frustrating. The 80 percent is that I’m fully committed. Despite the advice not to become emotionally invested, take things personally, or micromanage, I go all in. While being a bit of a control freak might have its downsides, clients appreciate that dedication. They might find it challenging initially, but once they’ve worked with me, they often want me for every other case.

From the client’s perspective, they know that even if I’m sending emails at 3 a.m. or pushing them to review a document, I’m doing it with their best interests in mind. It’s akin to having an exercise trainer: you might dislike them, but you appreciate the results when you’ve shed those pounds. There’s no magic formula, and my style isn’t for everyone. I am demanding, and I have uncompromising standards.

I can be rigorous and be a stickler for details. I often say there’s one right way to make your bed and an infinite number of wrong ways. My approach is to encourage doing things the right way, especially in tasks like discovery, where there’s a clear and effective way to proceed.

In essence, my attention to detail and the fact that I’m hands-on with most of the work set me apart. Clients appreciate seeing me and one associate on the bill rather than a lengthy list of associates. They value knowing that the work is done well when I’m involved.

What is something unique you offer to your clients?

I’d like to think I’m one of the best writers out there. I’m sure there are people who take depositions as well, if not better than me. I consider myself a strong advocate in the courtroom before a judge. However, my command of the written word makes me unique, and frankly, a lot of clients may not discern or appreciate the difference. The reality is that, for nine out of ten pieces of legal writing, it probably won’t make a significant difference, especially if the focus is simply on results, winning or losing the motion.

In that sense, you might question the necessity of uniqueness. So, okay, I wrote an A-plus brief. If it had been a B-minus, the outcome may have been the same. My joke to clients is “Here’s the good news: if this small motion in this local court somehow gets appealed to the US Supreme Court, I don’t need to do much more. I already did everything necessary for the original motion. I over-researched it and did all this stuff.” The bad news comes if the case is not going to be appealed to the Supreme Court. Then I have erred on the side of doing too much, but that’s who I am. I give it my all, make alternative arguments, and try to cover all bases to maximize the odds.

What is a personal or professional experience that has had a profound impact on your life and career?

People always tease me about quoting my dad all the time, but he has had the most significant impact on my life. He came from nothing, truly. He was a man of his word and a no-nonsense guy.

According to him, the biggest impact on his life among his four children (I have three siblings), came from my younger sister, who was born profoundly retarded—nobody likes the “R” word, but I like it. When people say someone’s disabled, you don’t know if they have a bad knee or if they have seizures, wet their pants, have a limited five-word vocabulary, and function at a one-year-old level. That’s what my sister was and what she operated at.

I took on a pro bono case for the facility where my sister lived. Facing formidable opponents, including the United States Department of Justice, the state of Illinois, the ACLU, and Equip for Equality, my team and I found ourselves challenging a settlement that we believed would adversely affect the disabled individuals in such facilities.

At the end of the nine-hour fairness hearing, my father, at the time in his late 80s, took an unexpected stand in the courtroom. His heartfelt testimony about the life lessons he learned from my disabled sister left an indelible mark. The judge, Chief Judge Holderman, who had initially been dismissive of our intervention, had a change of heart. He rejected the proposed settlement, ordered our intervention, and set the stage for two years of negotiations that prioritized the well-being of the residents.

Years later, at an award ceremony where Chief Judge Holderman honored me for Excellence in Pro Bono and Public Interest Service, I seized the opportunity to emphasize the sincerity of his commitment to justice. I handed him a piece of paper containing his preliminary thoughts from the night before the fairness hearing—a document where he had originally deemed our case futile. Witnessing his emotional response and acknowledgment of his own transformation was a powerful affirmation of the impact a dedicated legal advocate can have.

This case serves as a testament to the genuine pursuit of justice and the ability of the legal profession to create meaningful change. It is a source of immense pride, reminding me that victories in the courtroom extend beyond monetary gains and have the power to shape lives positively.

What is something you are grateful for?

I am grateful that my parents lived long enough to meet my kids and that my kids knew them. That’s important to me. And I have gratitude for the same thing we all have, which is an award of health. I am also grateful for finding one woman in this world who mostly understands me and puts up with me.

What are your sources of inspiration?

The strange thing for me is that happiness and inspiration come from largely unhappiness. I feel good when I can help fix a problem. This doesn’t have to be solving world poverty, global warming, or anything as big. For instance, I have one super sweet neighbor, about 85 years old. And I like helping shovel her yard when it snows—and she doesn’t even necessarily know who shoveled it.

Outside of work, what passions or interests do you pursue?

I enjoy nonfiction writing. When asked why I devote time to writing letters to the editor or op-eds, I joke that it’s a form of therapy that’s not only cost-effective but, hopefully, more impactful on the world.

Recently, I received a surprise email from a friend informing me that a brief letter I submitted a week before had made its way into the Chicago Tribune. The letter was a condensed version of my thoughts on current events, with a hint of sarcasm. In one sentence, I quipped, “Now that our mayor and the city council have solved the Middle East crisis, tackling crime, taxes, schools, and migrants should be a breeze.” The punchline stems from the Chicago City Council’s recent resolution on Israel, and this was my way of humorously expressing my views.

While I acknowledge that my writing often revolves around current events rather than fiction, it’s a satisfying endeavor that not only brings me joy but also holds the potential, however modest, to influence or contribute to meaningful conversations. So, when asked about my pursuits outside of work, writing remains a fulfilling and expressive outlet for me.

What is your favorite quotation?

I quote my dad a lot, and maybe his quotes weren’t original. One that I like is “Talk is cheap.” I grew up hearing that a lot. Another one I put on the signature block of my emails from Albert Einstein is “Curiosity has its own reason for existence.” Even though it can be annoying, as my wife will tell you, asking questions is generally a healthy habit that moves the ball.

What advice would you give your younger self?

I’d tell my younger self to be careful about what he wishes for, specifically regarding attending a prestigious school. While a great school is essential, it’s important not to confuse the brand with the education. I emphasize the significance of the brand by showing my Harvard law degree, even framed in Latin, highlighting its fancy nature. However, the point is not to be self-deprecating but to also highlight that I received a world-class education at the University of Illinois in Russian history and accounting.

I caution my younger self to recognize that goals are good, but understanding the why behind those goals is crucial. The brand may matter in our world, but it’s essential to differentiate between a brand and the actual education one receives. I reflect on my experience at Harvard Law School, where I felt I learned little compared to the rigorous education I received during my undergraduate studies.

I have concerns about the current emphasis on education and question the purpose of college today. I think the focus has shifted over the past few generations from being 80 percent about learning in a specific discipline and 20 percent about maturing and networking. Now, it seems reversed, with only 20 percent about learning the discipline.

In hindsight, I’d advise my younger self that if the goal is to be a lawyer, it’s unnecessary to obsess over perfect grades; just ace the LSAT and get into only one school. I have observed that many successful colleagues attended various schools and excelled in their craft. My joking advice to my younger self is to be careful about what I wish for because I might just get it.

While others might suggest that I should have advised my younger self to chill out and not take myself so seriously, I believe it’s valuable to be absorbed with a deep passion for something. I use the example of Girl Power Talk, emphasizing the importance of having one uniting passion to build around. I encourage my younger self and my children to find their “it,” the passion that drives them, without compromising or needing all the answers right away. The advice is to be passionate about something and let everything else follow in time.