Chicago Business Litigation Lawyer Blog
A lot of lawyers say they are “trial lawyers.” Then the case gets real. The judge sets deadlines. The other side files a motion that actually matters. A key witness gets cold feet. The documents tell a story your client does not like. That is the moment when you find out whether your lawyer is built for the courtroom or built for paperwork.
James V. DiTommaso is built for the courtroom.
James earned his J.D. from Chicago-Kent College of Law, and if you know Chicago-Kent, you know what that means. Chicago-Kent is not known for producing lawyers who hide behind the comfort of endless letters and endless “let’s see what happens” litigation. Chicago-Kent is known for its trial advocacy culture. The school’s trial program has been a national leader for decades, and its trial teams have competed and won at the highest level, including National Trial Competition championships in 1988, 2007, 2008, and 2015. That kind of environment changes how a lawyer thinks. It teaches you that credibility is everything, preparation beats improvisation, and the courtroom is not a place to “try something” for the first time.
That mindset is exactly what business owners need when the dispute is not theoretical and the money is not monopoly money.
Business disputes are personal even when the legal issues are corporate. A partnership fight can destroy a company faster than any competitor. A fraud case can shake a client’s confidence in everyone around them. A dealership dispute can trigger lender panic and manufacturer scrutiny. In those moments, you do not want a lawyer who is learning on your time. You want someone who treats litigation like it is a profession, not a hobby.
Chicago-Kent teaches that litigation is a craft.
James’s background at Chicago-Kent was not just a diploma on a wall. He earned a Business Law Certificate, and he was on the Dean’s List. He also served on the Executive Board for the Chicago-Kent Justinian Society. That combination matters because it is the intersection of two worlds that most lawyers do not blend well. Trial focused thinking and business focused judgment. Clients need both.
Here is the problem we see over and over again. A business owner wants an aggressive litigator. But the owner also needs practical advice that does not burn the company down while the lawsuit is pending. Too many attorneys pick one lane. They either posture, fight, and turn every issue into a war, or they hesitate, negotiate too long, and let the other side take advantage of the delay. James’s style is different. The approach is disciplined. The case is built methodically. The pressure is applied strategically. The goal is to win, but to win in a way that protects the client’s business and leverage.
Trial advocacy is not about being loud.
A strong trial lawyer is calm under fire because they know what matters and what does not. They know the difference between a motion that is theatre and a motion that changes the outcome. They know how to pin down facts early so the other side cannot rewrite history later. They know how to turn a messy dispute into a clear story a judge can understand and a jury can repeat.
That is what trial training gives you. Not swagger. Structure.
James brings that structure to the cases he handles at DiTommaso Lubin, P.C. Whether it is a business ownership divorce, a breach of fiduciary duty claim, a non compete dispute, a defamation case, or a high stakes commercial lawsuit, the plan is the same. Build the record. Control the narrative. Force the other side to commit to positions early. Expose contradictions. Then use that work to either settle on strong terms or take the case through trial.
If you have never been through litigation, here is something you should know. The most important work happens long before anyone says “your honor” in a courtroom. It happens when your lawyer is choosing the claims and defenses that actually fit the facts. It happens when your lawyer is preparing you for the deposition you are not excited about. It happens when your lawyer is reading the financial records with the mindset of a cross examiner. It happens when your lawyer is deciding whether to file for emergency relief because the business cannot survive delay. Continue reading ›