Chicago Business Litigation Lawyer Blog
Clients call us when they are in a sticky situation. That is usually not the first time something went wrong. The problem has been building. The partner stopped being transparent. The manager started siphoning business. The competitor started poaching customers. The contract got ignored. Then one day it becomes urgent. There is a hearing coming. There is a TRO on the table. There is a demand letter that cannot be ignored. The business owner suddenly needs answers that are both fast and correct.
In those moments, the lawyer who understands how judges think has a real advantage.
Before joining DiTommaso Lubin, P.C., James V. DiTommaso served as a judicial extern to Justice Thomas E. Hoffman of the Illinois Appellate Court, First District, Sixth Division. During that externship, he assisted in drafting opinions and bench memorandums. That experience is not just a resume line. It is a perspective shift. It teaches you what arguments actually move the needle inside chambers and what arguments sound good only to the lawyer making them.
Here is the reality most clients do not see. Judges are not looking for drama. They are looking for a principled reason to rule. They want clarity. They want credibility. They want to understand what the law allows them to do, and they want to do it without creating a mess.
When you have worked inside the appellate process, you learn quickly that the record is the case.
A business dispute can feel like a thousand moving pieces. But the court is going to rule based on what is properly presented, properly supported, and properly framed. That is why James’s externship experience matters in everyday business litigation. It pushes the case toward what courts value: organized facts, clean legal theories, and a timeline that makes sense.
A judge’s view of a contract dispute is not “who is angry.” It is “what does the contract say, what was performed, what was breached, and what remedy is available.” A judge’s view of a fiduciary duty case is not “who feels betrayed.” It is “who owed duties, what conduct crossed the line, what damages resulted, and what evidence proves it.”
That is the difference between storytelling and proof.
James applies that discipline to the cases he litigates. When a client is facing an emergency situation, the goal is not to file something fast and hope. The goal is to file something strong and specific. A motion for emergency injunctive relief only works if the facts are tight, the law is clear, and the harm is real. Judges can smell exaggeration. They see it every day.
The same is true in partner disputes and business ownership divorces. One side often tries to freeze out the other side by controlling information. That is not just unfair. It is a litigation tactic. The best response is not to yell about fairness. The best response is to use the legal tools available and build a record that shows the court what is happening in concrete terms.
A lawyer with appellate experience understands how orders are written and why that matters. The wording of an injunction can decide the next six months of the case. The language of a discovery order can determine whether you actually get the documents you need or you spend months arguing about loopholes. The framing of an issue can decide whether you win a key motion or you lose momentum. Continue reading ›