On the eighth day of trial, after just three hours behind closed doors, a Cook County jury returned a verdict that made history: $66M for the family of a 39-year-old mother of four who suffered catastrophic blood loss after a botched cosmetic surgery. It was the largest judgment ever against a plastic surgeon in Illinois.
For Craig Squillace, who helped lead the trial, the number wasn’t what mattered most. What stayed with him was the family – their grace, their courage and the way they told their story.
“They should have been celebrating Christmas together,” Squillace says. “Instead, it was another holiday without the person who meant everything to them.”
That verdict captured what defines Squillace’s style in the courtroom: quiet confidence and empathy. He prefers to let the work speak for itself, describing himself as a steady hand – someone who asks the right questions so a family can tell the story of its loss.
“I’m guiding them down the road with questions that let them tell their story,” says Squillace. “It’s not about me. It’s about helping the jury understand who this person is, what they went through and why it matters.”
It’s an approach that runs deeper than courtroom strategy. Squillace’s restraint – his willingness to guide instead of perform – has shaped his climb from college messenger to top partner handling some of Illinois’ most complex injury and wrongful-death cases.
For more than two decades, Squillace has built a career at Clifford Law Offices representing victims of catastrophic crashes, medical negligence and unsafe products. His docket reads like a map of human fragility: highway collisions, construction injuries, aviation disasters. In 2015, he secured a record $4M settlement in Will County for the mourning family of a woman killed in a trucking crash. He’s helped win multimillion-dollar settlements against automakers, tire dealerships and airlines – and in one case, an $11M settlement for the family of an insurance executive killed in a small-plane crash.
What’s kept Squillace at Clifford isn’t the verdicts but the people – the colleagues he works alongside and the clients he’s proud to represent. His approach is simple: “Treat every client as if they were your family.”
Lawdragon: Did you always know you wanted to be a lawyer?
Craig Squillace: I was very fortunate to be introduced to law while I was in college. I was a sophomore at Illinois State at the time and I heard through a mutual friend that this office had an opening. So I was coming home for breaks and working here in the back room in the summers and winters. I’d always been interested in government, it’s something that’s captivated me for as long as I can remember. So when I started working here and got to see how the system operated, it just clicked. I knew right then I wanted to become a lawyer.
Working for Mr. Clifford only deepened that feeling. You get to see incredible things happen here. When I was approaching the bar exam, Mr. Clifford offered me a position with the caveat that I had to pass the bar – which I did. I became an associate here and worked many years before being fortunate enough that Mr. Clifford elevated me to a partner.
LD: What did you learn from working with him?
CS: The client is always right. We are in a client-driven business, and if you're going to be successful in this business, you have to have an understanding of what the expectations are and what your client wants. One of the things I remember from early on, and I still hold this to be true, is he taught me you should treat every client how you’d want your family to be treated in a similar circumstance. That's important because most people have never been involved in litigation and they're hurt. So there's a stress level that exists and they're looking for you to reinforce that it's going to be okay. To let them know that we're not only on their side, but we're with them on this journey together.
LD: How else do you work with clients who have gone through traumatic events?
CS: People who’ve been through trauma need to feel validated – that what they’re doing, seeking representation and pursuing justice, is okay. It might sound simple, but many clients need reassurance that exercising their legal rights is completely justified.
Throughout the litigation, there are hard moments – frustration with how long things take, setbacks in recovery, grief that resurfaces around holidays. My role is to acknowledge those feelings, to let them know it’s okay to feel what they’re feeling. When clients feel seen and understood, it builds trust. They come to understand that you're more than just a lawyer; you're an advocate for them.
LD: Can you tell us about an early case where you really connected with a client – a moment that confirmed you’d chosen the right path?
CS: I remember a wrongful death case I handled in Will County – a 60-year-old woman who was killed, crushed between two semis. It was a terrible, tragic crash. She left behind two adult children, and her daughter was the administrator of the estate. I spoke with her constantly throughout the case.
Even today, every so often she’ll send a text just to say hello. What really stayed with me was how open she was about her grief and how this loss changed her life. My role wasn’t to fill the silence or try to fix everything – sometimes people don’t need you to talk, they just need you to listen. And in moments like that, you really understand what it means to do this work.
It might sound simple, but many clients need reassurance that exercising their legal rights is completely justified.
LD: Talk to me about your style in the courtroom.
CS: I am who I am – that's kind of my approach. I’m a straight shooter. I'm going to tell you this is how I practice and this is how we're going to work. One of the biggest things that I take pride in is that even though the defense is on the other side and they're advocating for their clients, it doesn't mean you can't respect them and you should because at the end of the day, they have a job to do just like we have a job to do. In the law, sometimes it’s okay to say thank you to opposing counsel. That doesn't make you weak.
LD: Did you always want to be a trial lawyer?
CS: Yes. I love the courtroom. I love being in front of a judge. To me, that's what being a lawyer is. I love the opportunity of being in front of a jury. When you're there advocating for your client and you're presenting the case or you've got your client on the stand and you're walking through an examination and seeing and watching how the jury reacts to different testimony or how the particular client may talk about an event or loss – seeing them connect. Those puzzle pieces, when the case comes together and you get to argue those pieces and see the jury connect the dots and put it together – it’s challenging, but also, that's the reward at the end of the day when the verdict comes in your favor.
LD: You’ve handled a wide range of motor vehicle cases over the years. What drew you to that area of practice, and are there any cases that stand out to you?
CS: Early in my career, I worked with Judge Robert Walsh, whose caseload included automobile, trucking and premises cases. My practice naturally evolved from that, and I found I really enjoyed the pace and variety. Every case presents its own challenges – no two are ever the same.
One that’s always stayed with me involved a teenager who suffered a traumatic brain injury while riding in the backseat of a car. It was a tough liability case. It took persistence and a lot of advocacy, but we reached a settlement that truly changed that young man’s life. Those are the kinds of outcomes that make this work meaningful.
LD: Can you recall any cases where you’ve gone into totally uncharted waters for yourself?
CS: I’ve handled many wrongful-death and personal-injury cases – everything from wrong-way drivers to complex premises liability claims. Those are some of the toughest cases because you’re often arguing over what someone should or could have done differently.
Every case presents its own challenges. Even when the legal framework is familiar, the facts are never the same, and you’re often dealing with situations that don’t fit neatly into a template. You have to evaluate what happened, what could reasonably have been done differently, and how to explain that clearly and credibly.
One case involved a woman with a severe knee fracture that led to years of surgeries and infections. Another involved a legally blind man struck by a commercial vehicle – a tough case where we still secured a recovery. I had a slip-and-fall case during a blizzard, where we proved the property owner created an unsafe condition while plowing snow.
Every case is different, but they all come down to the same thing: finding accountability in situations where life changed in an instant.
LD: What do you enjoy about learning something new, and how do you approach that process with each case?
CS: You have to carve out time for it. When a case falls outside your usual experience, you need to dig in – read, talk to experts and stay curious. I think as we get further along in our careers, it’s easy to assume we already know it all. But every case has its own nuances. If you stay open to learning, even after years of doing this, you’ll keep getting better – and your clients benefit from that.
LD: What can you tell us about the $66M verdict against the plastic surgeon last year?
CS: I was fortunate to try the case with with Brad Cosgrove. It was a horrific situation for Ms. Corcoles and her family. What resonated with the jury wasn’t just the defendants’ egregious conduct – it was hearing directly from her family. They spoke so beautifully about who she was, what she meant to them, and how deeply her loss was felt, especially with the holidays approaching.
All I did was guide them. They were the ones who told their story, and they did it with such honesty that it moved everyone in that courtroom. I was honored to be part of that team and to help a truly remarkable family get the justice they deserved.
LD: The jury deliberated for just three hours.
CS: Yes – they clearly understood the story. It was incredible and it was all because of the family.
LD: How long was the trial?
CS: Eight days. The verdict came down right before Christmas, on December 20th.
Every case is different, but they all come down to the same thing: finding accountability in situations where life changed in an instant.
LD: With regards to your current caseload, are there any trends you’re seeing?
CS: A lot of my work right now involves wrongful-death auto cases – families who’ve lost loved ones in collisions. One of the toughest parts is dealing with limited insurance coverage. You sit across from someone who’s lost their mother or son, and you have to explain that the available policy is $25,000 or $50,000. No amount will ever reflect that loss, but sometimes that’s all there is. It’s one of the hardest realities of this work.
I’m also seeing more cases involving rideshare drivers. Uber and Lyft have completely changed the landscape – not just how people get around, but how we handle these cases. Fewer young people even want to drive now, and the old taxi market has almost disappeared. The challenge is that the legal side hasn’t caught up. Most people don’t realize what they’re agreeing to when they click through those rideshare terms, and that creates real hurdles when something goes wrong.
LD: What do you find most fulfilling about your work and your career?
CS: I know it sounds cliché to say helping people, but it’s the truth. Because of my caseload, I meet people from every walk of life. Every story, every problem is different – and I learn something from each one. But I remember one case that’s always stuck with me. The defendant had a rare neurological disease that caused him to lose control one day and drive the wrong way, hitting a family. My clients suffered terrible losses, but the defendant and his family were suffering too – through no fault of their own.
When I took their depositions, I had a choice: go in hard, or treat them with compassion. I chose the latter. There was no need to be cruel. They were living their own nightmare. That’s what this work reminds you of – everyone has pain, and empathy goes a long way.
LD: What advice would you give to younger lawyers who are working in this space?
CS: Be authentic. I think a lot of times when you start out, you try to be someone you're not, and when you do that, you get yourself in more trouble than you should. Become okay with criticism. The criticism is there to help you evolve. I think everyone's a little scared to ask questions; no one wants to admit that they may not know something. But remember – it’s called the practice of law for a reason. So ask questions because that allows you to learn and become a better attorney, not only for your clients, but for the firm.
LD: What do you like to do outside of the office?
CS: I enjoy cooking. I enjoy spending time with my family. I want to soak up quality time with my kids, my wife and my dog. That's where I find the most enjoyment.
